Category: Politics

CHICAGO — Former Illinois Rep. Jesse Jackson Jr. fell short in his attempt to return to Congress on Tuesday, after resigning more than a decade ago amid a federal corruption investigation.

Cook County Commissioner Donna Miller defeated him and a host of other candidates to win the Democratic primary for Illinois’ 2nd district, a seat currently held by Rep. Robin Kelly, who left to run for the Senate.

Jackson’s comeback bid transformed the race into a high-profile showdown, with the former representative leaning on his deep name recognition. But Jackson — who resigned in 2012 and served prison time after pleading guilty to wire and mail fraud for misusing $750,000 in campaign funds — was unable to successfully reframe his past as a redemption story.

Meanwhile, Miller consolidated support across key parts of the district and benefited from spending by a group aligned with the American Israel Public Affairs Committee, which funneled more than $4 million into ads promoting her campaign. The contest drew national attention in part because the group, Affordable Chicago Now, gave Miller’s campaign substantial airtime in the Chicago media market and funded mail pieces highlighting her record.

The spending helped elevate Miller’s profile even as a separate political action committee, the Leading the Future PAC, which is funded by OpenAI stakeholders, spent more than $1 million to promote Jackson after he signaled support for the industry with op-eds and ads.

Miller focused her campaign on her work on public health, public safety and budget oversight. She also underscored her longstanding ties to Democratic women’s organizations, as vice president of Illinois Democratic Women, former president of the Democratic Women of the South Suburbs and past board chair of Planned Parenthood of Illinois and its political action committee.

She made a concerted effort not to attack her opponents, saying she was “the only candidate in the race” to do so.

Other notable names in the race included state Sens. Robert Peters and Willie Preston.

The 2nd District, which stretches from Chicago’s South Side into the south suburbs and rural counties, is heavily Democratic and Miller is expected to win easily in November.

​Politics

The Illinois primaries have seen gobs of spending, both in the highly watched Senate race and further down the ballot in competitive open House seats.

Groups affiliated with the American Israel Public Affairs Committee have poured millions of dollars into key contests, potential 2028er and Democratic Gov. JB Pritzker has found himself at odds with several prominent Black leaders in the state, and generational fights continue to plague the Democratic Party post-2024.

Here’s what POLITICO is watching today.

Can AIPAC avoid another fumble?

AIPAC faced backlash from moderate Democrats last month after inadvertently boosting a progressive candidate in New Jersey who said Israel has committed a genocide in Gaza. It’s hoping not to make the same mistake again.

The group is facing a major test of its political muscle in Illinois as Democrats increasingly scrutinize Israel and AIPAC itself. It’s spending heavily in several House races, most notably in the contest to replace retiring Rep. Jan Schakowsky in the 9th district.

But Democratic strategists have warned that the group’s attacks on Evanston Mayor Daniel Biss — the grandson of a Holocaust survivor who has criticized Israel — have created a late opening for progressive insurgent Kat Abughazaleh, a Palestinian-American who’s an even more vocal critic, rather than effectively boosting the AIPAC-preferred candidate, state Sen. Laura Fine. AIPAC has made a sharp pivot in the final stretch of the campaign, turning its focus squarely on Abughazaleh instead.

“There’s been a strategy shift,” said a person directly familiar with AIPAC’s thinking, granted anonymity to discuss private conversations. “Our primary goal in Illinois is to prevent potential ‘Squad’ members from being elected to Congress.”

The big question for Tuesday will be whether that change in strategy happened too late to avoid another embarrassment for AIPAC.

Will JB’s involvement help or hurt him?

Pritzker has been vocally supporting, and heavily funding, Lt. Gov. Juliana Stratton’s campaign for Senate against Reps. Raja Krishnamoorthi and Robin Kelly. That move has rankled some prominent Black leaders.

“A sitting governor shouldn’t be heavy-handing the race,” Congressional Black Caucus Chair Yvette Clarke, whose caucus is supporting Kelly, told Punchbowl earlier this month. “Quite frankly, his behavior in this race won’t soon be forgotten.”

The worry from Black Democrats is that Kelly and Stratton — both Black women — could end up splitting the Black vote, with Pritzker’s endorsement driving that wedge further. That may help Krishamoorthi win the race and kill their chances of electing a Black woman to the Senate this cycle.

Krishnamoorthi has led most public polls of the race and had a big cash advantage early on, allowing him to get up on TV earlier than his opponents. Pritzker’s money has helped Stratton close the gap, while Kelly sits in third in most public polls.

“People are conflicted as to whether or not they should go with the best candidate who they like, or do they go with what the polls are saying as the most viable candidate,” former Democratic Chicago Mayor Lori Lightfoot, who supports Kelly, said in an interview last week. “That’s the tension and the conflict that I’m hearing kind of across the board, but particularly among Black Illinoisans.”

What do all the races say about the future of the Democratic Party?

Both the Israel debate and racial tensions — as well as the growing generational divide in the Democratic Party — have dominated Illinois’ primary contests.

Tuesday’s results will be another early test, following Texas earlier this month, for where the party is headed as it still grapples with across-the-board losses to Republicans in 2024.

How do the outside influences fare?

More than $35 million has been poured into TV ads on Illinois races, according to AdImpact, with tech interests leading the way: pro-AI and pro-Crypto industry groups have combined to spend more than $15 million. It’s a dizzying sum that has shocked many veteran Illinois political strategists who are long accustomed to bruising campaigns.

Some candidates have openly courted — and practically begged for — support from these groups. Former Rep. Jesse Jackson Jr. — who is running to reclaim the IL-02 seat he once held — used AI in an ad to enhance former Rep. Bobby Rush’s voice (D-Ill.) after it was damaged from treatment he underwent to battle throat cancer.

The groups’ huge spending to get allies in Congress could shape the heated policy debate over how to regulate two fast-growing industries. How well their chosen candidates fare will help guide their future spending later this year.

Who turns out?

Turnout among Hispanic voters was a strong point for Democrats in the Texas primary, not to mention several special elections in recent months, driven by backlash to the Trump administration’s aggressive immigration enforcement along with continued economic uncertainty.

We will see whether that continues in Tuesday’s primaries, particularly in Chicagoland — which was shaken by a deportation blitz of its own last fall but where most of the primaries are for safe blue seats.

There’s also the question of turnout in primaries where support for Israel has been a major issue. A Senate primary should bring voters to the polls across the state, but POLITICO will be watching for how much higher turnout is in the 2nd, 7th, 8th and 9th districts to gauge how much Democrats’ intraparty disagreements about the issue — and the flood of outside money that has come with that — uniquely drives voting.

Alec Hernández and Jessica Piper contributed to this report.

​Politics

CHICAGO — The American Israel Public Affairs Committee is making a nearly $22 million bet in Illinois that its money, if not its policy views, can still hold sway in Democratic politics.

In three of the four Illinois House races it’s targeting, AIPAC appears to be using shell PACs to largely conceal where that money is coming from rather than spend from its main super PAC vehicle, United Democracy Project. Like in other recent contests, their ads focus on anything but Israel.

But AIPAC appears at risk of inadvertently helping the candidate most hostile to its views in the race to replace retiring Rep. Jan Schakowsky — just as it did in New Jersey last month. The group has taken a sharp tactical shift in recent days, pivoting from attacking a Jewish candidate who has criticized Israel and focusing instead on a Palestinian-American candidate who has been more outspoken.

Interviews with a dozen Democratic elected officials, candidates and strategists — including both supporters and critics of Israel — revealed growing concerns about AIPAC’s interventions. Strategists warn that AIPAC’s attacks on Evanston Mayor Daniel Biss, the grandson of a Holocaust survivor, created an opening for progressive social media influencer Kat Abughazaleh, a Palestinian-American who is a vocal critic of Israel and appears to have late momentum in the race, over AIPAC’s preferred candidate, more moderate state Sen. Laura Fine. In the past week, the group has pulled down all of its anti-Biss messaging, but it could prove too late.

“There’s been a strategy shift,” said a person directly familiar with AIPAC’s thinking, granted anonymity to discuss private conversations. “Our primary goal in Illinois is to prevent potential ‘Squad’ members from being elected to Congress.”

Tuesday’s primary will be the first test of AIPAC’s political muscle in the 2026 primary season after amassing nearly $100 million in its warchest, even as polls show more and more Democrats have negative views of Israel — and of the group itself.

“AIPAC may deliver another candidate who is plainly not on their agenda and … the concerns about their interventions within the primary electorate are only going to intensify,” said David Axelrod, a longtime Chicagoan and former senior adviser in President Barack Obama’s administration. “These ads are not branded as AIPAC for a reason, so there’s a recognition that they are a controversial presence in Democratic primaries.”

AIPAC recently spent $2 million to sink former Rep. Tom Malinowski (D-N.J.) in a special election primary. Malinowski, a pro-Israel moderate who would not support unconditional aid to Israel, lost to Analilia Mejia, a progressive organizer who has said Israel committed genocide in Gaza. The move infuriated centrist Democrats, who saw it as a spectacular self-induced fumble — and are worried it may be happening again.

“No one wants to see another New Jersey 11 … and everyone should be concerned about it happening,” said one Democratic donor adviser close to AIPAC who was granted anonymity to speak candidly about the dynamics.

The organization has become increasingly controversial on the left for its full-throated support of Israel’s war in Gaza and is facing a new layer of hostility in the wake of Israel’s joint attack with the U.S. in Iran. Among Democrats, 62 percent think America is too supportive of Israel, compared with just 22 percent who think the support is about right and 8 percent who think it’s not supportive enough, according to a Quinnipiac University poll released last week.

Democratic candidates and strategists expect AIPAC to intervene in a range of House primaries in the coming months, as well as the Senate primaries in Michigan and Minnesota. They’re watching to see how the group’s interference plays with voters amid the backdrop of the war.

“You’re going to see more of this unfortunately” across the country, said former Chicago Mayor Rahm Emanuel, a noted Democratic strategist now weighing a run for president, of the influx of outside spending — from AIPAC to crypto groups. “Illinois is literally the first stop on the way to an ugly future, where billionaires will be the dominant players and candidates will be pawns in their world.”

In Illinois, an AIPAC-aligned super PAC called Elect Chicago Women, had spent heavily against Biss on TV and digital ads, while also spending more than $4 million on TV ads and mailers boosting Fine. In recent days, another AIPAC-aligned group, Chicago Progressive Partnership, put out ads attacking Abughazaleh and propping up another progressive in the race, Bushra Amiwala, in an apparent effort to split the vote.

Local strategists noted the abrupt shift when the Biss attacks stopped earlier this month.

“It looks like they’re changing their tactics” after the New Jersey backfire, said an Illinois Democratic lawmaker, granted anonymity to discuss the issue candidly. “Is there evidence that [AIPAC] is adapting and taking lessons from the last election? Yes.”

Biss, for his part, predicted there would be “backlash” to AIPAC’s moves in Illinois in future primaries.

“They’ve chosen to make clear that it’s unacceptable to them to have members of Congress who don’t believe in a no strings attached blank check of military aid to the current Israeli government, no matter what they do in Gaza,” Biss said “So that’s what people in the district and around the country will be interested to see what the outcome is.”

Abughazaleh sees the shift to attack her as a sign that AIPAC is “panicking” to control the race. “They’re realizing that they didn’t take us seriously, and that people aren’t looking for the status quo. So they are panicking,” she said in an interview.

Fine has opposed adding conditions to U.S. aid to Israel, though she has expressed general frustration at the role of “dark money” and the lack of transparency from political action committees, saying it’s “a big problem in our political system.”

AIPAC’s super PAC declined to comment on its involvement in Illinois, including its use of pop-up super PACs to filter funds to candidates. AIPAC spokesperson Deryn Sousa said in a statement, “Our members are focused on building strong bipartisan support for the U.S.-Israel partnership in the 120th Congress.”

The group is also spending heavily for its preferred candidates in the races to fill seats left open by Reps. Robin Kelly and Raja Krishnamoorthi, who are running for the Senate, and Danny Davis, who is retiring.

AIPAC’s allies are not confident about their chances in Kelly’s district. The group is backing Cook County Commissioner Donna Miller, but former Rep. Jesse Jackson Jr. (D-Ill.) has been bolstered by more than $1 million in spending from a pro-cryptocurrency super PAC. Plus, he has sky-high name recognition, especially in the wake of the recent death of his father, the Rev. Jesse Jackson Sr.

Pro-Israel Democrats feel more confident their preferred candidates can win in two other races.

Chicago City Treasurer Melissa Conyears-Ervin has benefited from nearly $5 million in positive ads from AIPAC’s main super PAC, United Democracy Project, in a crowded 13-candidate primary for Davis’ seat. State Rep. La Shawn Ford has strong name recognition in the district and Davis’ endorsement, but he has struggled to keep up with fundraising.

In Krishnamoorthi’s district, moderate former Rep. Melissa Bean has benefited from nearly $4 million in supportive messaging from the “Elect Chicago Women” group that’s also supporting Fine in the 9th.

AIPAC’s critics argue that the group’s moves in Illinois, particularly concealing the funding sources of its super PACs, demonstrate that “they themselves understand how toxic they are,” said Jeremy Ben-Ami, president of the progressive J Street group, which bills itself as “pro-Israel, pro-peace.”

“In every part of their political work, they’re doing this surreptitiously,” he added.

Jessica Piper and Andrew Howard contributed to this report. 

​Politics

HOCHUL’S AD CAMPAIGN: Gov. Kathy Hochul’s office is using taxpayer money to fund an advertising blitz promoting her agenda, brushing up against a ban on governors appearing in promotional material.

State law prohibits elected officials from appearing in ads paid for with state funds.

Hochul doesn’t directly appear in any of the ads. Instead, they encourage people to visit a state-run website where she’s prominently featured talking about wanting to cut red tape to build affordable housing.

“They’re skirting the very intent of what that law was meant to do, and that’s using taxpayer dollars to promote the image or likeness of the governor,” Republican Assemblymember Matt Slater said. “It’s clearly something that needs to be looked into so we can figure out what consequences she should be facing if she is in fact violating the law.”

The ads have appeared over the past week on Facebook, YouTube, and at least one billboard. The governor’s office said a FOIL request would be required to see the full scope.

One example is a YouTube commercial that simply states “Let Them Build” and directs people to the state’s website. The Executive Chamber has spent between $10,000 and $15,000 on that ad — one of 21 to air on YouTube or Google over the past week. The ad has been viewed one million times.

“The state routinely engages in awareness and education campaigns on critical policy priorities and this campaign was designed in compliance with all ethics laws,” said Hochul spokesperson Jen Goodman.

Reinvent Albany’s Rachael Fauss said that if the 20-year-old law had been written today, “it probably would take into consideration” campaigns like this.

“From a technical perspective, she may not be violating the law,” she said. “But I think the spirit of the law is to not have the governor’s likeness be promoted through the use of taxpayer funds. That was the intent of it. Unfortunately, this is an area where the law hasn’t kept up with the way people consume media and ads these days.”

The ban on advertising came about after former Gov. George Pataki ran state-funded commercials during an election year in which he encouraged people to register in a new healthcare program. Ethics reforms passed as part of former Gov. Eliot Spitzer’s inaugural agenda included language prohibiting the practice.

Hochul isn’t the first elected official to brush up against the intent of the law in recent months. New York City Mayor Zohran Mamdani’s likeness has appeared on WiFi kiosks, a practice that’s permitted since the city is given the screentime for free. And Mamdani, unlike Hochul, isn’t up for reelection anytime soon.

“She’s got plenty of campaign funds that she could be using to pay for these things,” Slater said. “What she’s doing right now is spending taxpayer money to enhance her image when she’s on the ballot this year.” — Bill Mahoney

FROM THE CAPITOL

PRICING POLITICS: Democratic state Attorney General Letitia James is throwing her support behind a bill meant to crack down on retailers’ use of algorithmic pricing.

James was in Albany this morning to back legislation meant to halt the practice, which uses a consumer’s personal data to set individually tailored prices.

The bill, backed by Assemblymember Michaelle Solages and Deputy Senate Majority Leader Mike Gianaris, is part of a broader push being made by elected officials to address peoples’ pocketbook concerns.

“This online pricing model hits hardest where it hurts the most — food, medicine, diapers and other essentials,” James said at a news conference. “We all have all been focused on the issue of affordability across this state.” — Nick Reisman

FROM CITY HALL

EVIDENCE HUNT: The former NYPD sergeant accusing former mayoral aide Tim Pearson of sexual harassment wants to get her hands on the evidence that prompted the Mamdani administration to stop paying for Pearson’s legal bills.

In 2024, the former sergeant, Roxanne Ludemann, sued Pearson, a confidant and top adviser to former Mayor Eric Adams, accusing him of sexually harassing her at work and then professionally retaliating against her when she rejected his overtures.

Thanks to an unusual arrangement greenlit by Adams’ Law Department, Pearson received taxpayer-funded private lawyers to defend him against Ludemann’s suit. But Mamdani’s corporation counsel, Steve Banks, announced last week that he had rescinded Pearson’s arrangement, citing unspecified “new evidence” that warranted terminating it.

In a court filing late Friday, John Scola, an attorney representing Ludemann, demanded that the Law Department provide his client with access to the evidence in question, arguing it’s relevant to her ongoing case.

“Produce all documents, records, evidence, reports, memoranda, and materials of any kind that constitute, refer to, or relate to the ‘new evidence’ relied upon, reviewed, considered, or referenced by corp counsel in making its determination to decline or withdraw representation of Defendant Timothy Pearson in this matter,” Scola wrote in the filing.

Also last week, Banks terminated a similar arrangement that allowed Jeffrey Maddrey, an Adams ally and former NYPD chief of department, to receive taxpayer-funded attorneys in the Pearson matter, too. Maddrey is accused by Ludemann of helping Pearson retaliate against her.

Scola’s filing demanded access to the information that prompted Banks to slash Maddrey’s arrangement as well.

Pearson and Maddrey, who resigned from city government in late 2024 after being ensnared in unrelated corruption investigations, have denied any wrongdoing.

A Law Department spokesperson did not comment when asked today about Scola’s demand.

New York City taxpayers have already paid more than $620,000 to cover Pearson’s legal tab alone. — Chris Sommerfeldt

FINANCE SHUFFLE: Mamdani is zeroing in on a pick to run the Department of Finance, a normally under-the-radar agency that has taken on new prominence amid the mayor’s push to raise property taxes.

Mamdani’s administration is in talks to hire Richard Lee for the job, according to three people with knowledge of the discussions who were granted anonymity to discuss an internal personnel matter.

Lee currently serves as director of the City Council’s Division of Finance. That means his move to Mamdani’s finance department would leave Council Speaker Julie Menin without her top budget adviser amid increasingly tense negotiations over the city’s $127 billion spending plan for the upcoming fiscal year.

The Council is conducting budget oversight hearings throughout the month to better ascertain how city agencies are planning to operate amid a precarious fiscal situation. The city is facing a projected multi-billion dollar deficit over the next fiscal year, and Mamdani’s administration is relying on cash reserves, optimistic revenue projections and an increase in property taxes to bridge that gap and balance the spending plan for the fiscal year beginning July 1.

Increasing levies on property owners would require approval from the Council, and Menin has dismissed the idea as a nonstarter. She has argued the city needs to look for other ways to cut costs beforehand. The mayor, by contrast, says drastic steps like property levy hikes can be avoided if Albany gives the city the authority to raise local taxes on millionaires and corporations — proposals Menin has declined to support.

Lee, should he ultimately join Mamdani’s administration, would be working for the finance department as it tabulates a key variable — the assessed value of property in New York City — which helps determine how much revenue the city collects from owners each year.

Read the story from Joe Anuta and Chris Sommerfeldt in POLITICO Pro. 

AROUND NEW YORK

— MACHIAVELLIAN MAMDANI: The mayor forced his political will on fellow lefty lawmakers, including by squashing Tiffany Cabán’s congressional prospects and threatening Chi Ossé. (The New York Times)

— ADAMS OFFICIAL UNDER PROBE: The former commissioner of the city’s probation department under Mayor Eric Adams is being investigated by the Manhattan district attorney. (Gothamist)

— MAYOR DINES WITH KNICKS: Mamdani broke his Saturday Ramadan fast with Senegalese Knicks player Mo Diawara. (GQ)

Missed this morning’s New York Playbook? We forgive you. Read it here.

​Politics

President Donald Trump is bringing back 2020. Many Republicans wish he wouldn’t.

Conversations with nearly a dozen GOP state and county chairs and strategists reveal a party largely eager to move on from relitigating Trump’s election grievances, which they’re worried may detract from an economic message that actually motivates voters. But the president won’t let it go, subpoenaing 2020 election records and putting pressure on lawmakers to pass legislation to overhaul voter registration laws.

As Republicans stare down a treacherous midterm landscape, there’s a growing view inside the party that focusing on “stolen election” claims and voter fraud will kneecap them in the general election: That messaging might play well with the MAGA base in the primary, but it could alienate moderates tired of rehashing an election from nearly six years ago.

“I’m always one to believe you should look forward, not backward,” said Charlie Gerow, a Pennsylvania-based GOP strategist and Trump convention delegate who hosted a meeting of fake electors in 2020 at his Harrisburg-based public affairs firm. “It would be better if the midterms focused on the recovery of the economy and all the good things the Republican administration and Congress are doing to move the economy forward.”

In recent weeks, Trump has turned his sights on Maricopa County — Arizona’s largest county — subpoenaing records just weeks after the FBI raided an elections office outside Atlanta. He has revisited grievances that the 2020 election was “rigged,” suggested Republicans should nationalize elections and is demanding that lawmakers make passing the SAVE America Act, which would put in place stricter voting requirements, their “No. 1 priority.”

“Part of me understands it, and part of me just wants to move forward,” said Todd Gillman, chair of the Monroe County Republican Party in Michigan.

“Focus on the things that matter to everybody throughout the whole country,” he said, “or we’re going to have a problem in a few months.”

Trump does have backing from a number of Republicans, including some battleground-state GOP chairs who are not only embracing the president’s election probe, but openly encouraging his administration to audit their states’ records as they continue to push allegations of fraud from 2020.

Bruce Parks, the chair of the Washoe County, Nevada, GOP, said he would “absolutely” welcome a probe into his county and Clark County, the two largest in the state. And Jim Runestad, the chair of the Michigan Republican Party, suggested a review of records in Detroit, long a focal point of Trump’s 2020 election conspiracies.

“There’s no problem at taking a look at this and making sure everybody’s comfortable,” Runestad said.

Still, others say the risk is that voters simply don’t care — or have moved on. Republicans, including Trump’s own advisers, increasingly want him to focus on the economy ahead of the midterms.

That comes as polling repeatedly shows that economic issues — not election issues — top voters’ list of concerns. In a February POLITICO Poll, more than half of all Americans — 52 percent — said the cost of living was a top issue facing the U.S. By comparison, less than a quarter — 23 percent — said a top issue was the U.S.’ democracy being under threat, a view held predominately by Democrats.

Those cost of living worries are now being exacerbated by Trump’s war in Iran, which is driving up gas prices and wreaking global economic havoc as it enters its third week.

The White House said Trump’s efforts are aimed at restoring confidence in elections and reiterated the importance of passing the SAVE Act.

“[Trump] is committed to ensuring that Americans have full confidence in the administration of elections, and that includes totally accurate and up-to-date voter rolls free of errors and unlawfully registered non-citizen voters,” spokesperson Abigail Jackson said in a statement.

Buzz Brockway, a GOP strategist and former state representative in Georgia, called election issues a “huge distraction,” adding: “Nobody outside of a small dedicated group are talking about this, they’re talking about the economy, they’re talking about, now, the price of oil.”

In Georgia, long an epicenter of Trump’s repeated efforts to litigate the 2020 election, some Republicans say voters are now largely “immune” to the issue that’s been rehashed endlessly for the past five years.

Some state-level GOP officials are hoping Congress passes the SAVE Act — despite the reluctance of many Republican lawmakers — so it will give them enough cover with MAGA voters but allow them to avoid talking about election issues themselves.

While Trump’s “stolen election” claims may still be a driving force for some primary voters, the general electorate is focused elsewhere. And if Republicans make those grievances central to their midterm message, they risk falling into a similar trap Democrats confronted during the 2024 presidential election — when former Vice President Kamala Harris’ warnings about democracy won over already loyal Democrats but failed to sway enough of the swing voters she needed to clinch the presidency.

“You’ve got to at least touch that base,” said one Georgia-based GOP strategist, granted anonymity to speak candidly. But “once you’ve got the nomination, then I think it really collapses down into economic issues.”

That dynamic can create a political conundrum for Republican candidates.

“A savvy Democrat will put a candidate on the spot and say, ‘You agree with [Trump], don’t you?’ and make a mess,” Brockway said. Republicans have “got to figure out a way to deflect that question somehow, in a plausible way that doesn’t alienate this loud minority.”

​Politics

In the 15 days since President Donald Trump launched Operation Epic Fury on Iran, Sen. Ruben Gallego (D-Ariz.) is approaching nearly a dozen media appearances, offering his often visceral reaction to the conflict.

Gallego, a 46-year-old combat veteran who deployed to Iraq as an infantryman in 2005, has emerged as a blunt, clear voice for the Democratic Party on foreign policy, speaking as someone whose own generation experienced the forever wars.

There he was on CNN’s “The Source with Kaitlin Collins” saying Secretary of State Marco Rubio was doing “CYA” and noting that the “MAGA base is pissed.” There he was sitting down with the AP speaking “as someone who lives with PTSD,” adding “it’s not been an easy week.” And there he was on Derek Thompson’s podcast, speaking about “going town to town searching for insurgents” 21 years ago, “but there was no clear direction of what victory looked like, what the end goal was, what was going to be the after-action report on Iraq.”

Gallego isn’t alone. Sen. Mark Kelly (D-Ariz.), a Navy captain who flew combat missions during Operation Desert Storm in 1990, has also racked up a run of high-profile media appearances, as has former Transportation Secretary Pete Buttigieg, a U.S. Navy Reserve intelligence officer who deployed to Afghanistan. Maryland Gov. Wes Moore, who served in Afghanistan in the Army’s 82nd Airborne, went on local radio this week to link Americans’ affordability woes to the war.

In a year after many Democrats pined for a metaphorical fighter, the party is now having a conversation with itself about whether it needs a literal fighter — a veteran who can speak with credibility on issues of war and national security.

In an interview with POLITICO, Gallego spoke of “dodging bullets, IEDs, RPGs, clearing towns and then coming back to the same towns with insurgents” and of “losing friends and still not understanding what the end goal was the whole time.”

“It leaves a mark on you, and you start seeing it happening again, you know, you don’t really think about the politics,” Gallego said. “You think about the people who are going to be potentially dying. And that’s why I think I was not hesitant to speak my mind on that.”

Later this month in San Antonio, Texas, Gallego will join VoteVets Action for its third town hall featuring potential 2028 Democratic presidential candidates, promising “fresh voices to the national conversation — those who have worn the uniform and served alongside us, who connect with everyday Americans others can’t,” according to a promotional video. (They’ve also done town halls with Buttigieg and Michigan Sen. Elissa Slotkin.)

“On foreign policy, the Dems need a candidate who is seen as strong/tough — not in rhetoric or bravado political platitudes but who conveys a sense of judgement and resolve with which voters connect instinctively,” said Doug Wilson, the former assistant secretary of Defense for Public Affairs during the Obama administration and co-lead of Buttigieg’s 2020 foreign policy team.

The “Iran war underscores the need” for such a candidate, Wilson added.

Whomever the Democrats select as their nominee could potentially face a Situation Room-steeped ticket deep with national security credentials, including a Marine Iraq war veteran in Vice President JD Vance or Rubio, with his secretary of State experience.

Depending on how the many conflicts the U.S. is engaged in at the moment resolve, that experience could cut against them.

But right now, Democrats who can match those bona fides have some currency others without them can’t.

“That’s obviously going to be helpful to them,” said Matt Bennett, co-founder of the center-left think tank Third Way. “It’s gonna be a big part of what they’re talking about for the next little while. But you know, how long does it last? We just don’t know, right? In my professional lifetime, foreign policy stuff and national security has mattered in a presidential race once — in 2004. That’s it. Otherwise, it comes up, but it’s not driving the conversation.”

Some potential Democratic candidates without such credentials have still managed to break through amid the Iran news cycle. Sen. Jon Ossoff (D-Ga.) has said the White House has treated aspects of the war “as a video game,” in a clip gaining traction on X. “When American service members killed in action are returning to the United States in flagged-draped coffins, and even more Americans have lost limbs or suffered terrible brain injuries or are fighting for their lives, this White House treats war like a game, and it’s a disgrace,” Ossoff said.

When asked whether military service is an essential for the party’s eventual nominee, Gallego acknowledged there is a benefit for someone who can “speak with that type of credibility.”

“I’m not the type of person that’s like, ‘you have to be a veteran — Iraq War veteran,’” Gallego said. “This is a democracy. We’re still one, and there’s a lot of people that can bring valuable experience and knowledge. But you know, someone that actually has a nuanced understanding of foreign policy; that doesn’t go to the total knee-jerk reactionism that sometimes we see where we go to the point of, you know, isolationism; or the other way, where we go to full neocon. There needs to be a very balanced way to how we approach the world.”

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​Politics

Rep. Andy Barr (R-Ky.) has locked down his House district for over a decade. Democrats think his Senate bid presents them an opening in a seat that has raced away from the party.

Kentucky’s 6th District — anchored by Lexington in the heart of the Bluegrass State — hasn’t elected a Democrat to Congress since Ben Chandler in 2010. Barr has held the seat since 2013 and has proven difficult to dislodge. The last time a Democrat came close was in 2018, when fundraising juggernaut Amy McGrath came within about 3 points of defeating him.

But Barr won his last reelection in 2024 by 26 points, outperforming President Donald Trump, who carried the district by 15 points according to calculations from The Downballot.

If Barr had sought another term, Democrats privately concede they stood little chance.

But with Sen. Mitch McConnell (R-Ky.) retiring and Barr opting to run for his seat, a rare open seat is now in play — and firmly on Democrats’ target list.

In the Democratic primary, two candidates have emerged as frontrunners, according to national Democrats watching the race: Zach Dembo, a Navy veteran and former federal prosecutor, and Cherlynn Stevenson, a former Kentucky state representative. Each is offering a different theory for how to flip the deep-red district.

The question of how a Democrat could win the seat dominated a Democratic primary debate earlier this month, where candidates leaned on sharp criticisms of the Trump administration, ranging from its decision to strike Iran to affordability issues as a result of the president’s tariffs.

Stevenson has branded herself a “Mountain Democrat,” leaning into her Appalachian roots and pitching herself as someone who could mend the disconnect between the party and rural voters by focusing on cost-of-living pressures and access to affordable health care. She said her upbringing in a small mining town in eastern Kentucky and years living in Lexington allow her to bridge the district’s urban-rural divide.

“Winning right here in Kentucky requires cultural fluency and trust,” Stevenson said in an interview. “I know how to talk to working families, rural communities and independents because I am one of those people.”

She’s also got experience flipping seats. She was the first woman and first Democrat elected to represent Kentucky’s 88th state House district, where she also served as state House minority caucus chair.

Dembo, meanwhile, is pitching himself as a “Beshear Democrat” — a nod to Democratic Gov. Andy Beshear, who performed well in the 6th District during his 2023 reelection campaign.

“This is 100 percent a flippable district,” Dembo said in an interview, pointing to headwinds from “all of the terrible decisions of this Republican Congress.”

He has emphasized his experience as a Navy JAG officer and former federal prosecutor, arguing his resume gives him crossover appeal in a Republican-leaning district. Dembo resigned from his position at the Justice Department during Trump’s second term, saying he could no longer remain in his role amid what he described as corruption and the Trump administration’s “abuse of the criminal justice system.”

Both Dembo and Stevenson have posted solid fundraising numbers. And Republicans have a contested primary as well, in a race that includes state Rep. Ryan Dotson and former state Sen. Ralph Alvarado.

“We’re giving Republicans a run for their money in places that they never thought they would have to compete before, and now they do,” said DCCC spokesperson Madison Andrus.

But the race will still be incredibly challenging for Democrats, even though the DCCC has had the seat on its “Red to Blue” battleground list. Kentucky’s federal delegation remains overwhelmingly GOP. The seat also got nominally redder during the post-2022 redistricting process, making it even tougher terrain than during McGrath’s close call in the last Trump administration midterms eight years ago.

Most election watchers believe the seat is well outside the core House battleground as well, and it has not attracted notable outside spending, underscoring how steep the climb would be for Democrats to win even without an incumbent on the ballot.

Republicans dismissed the Democrats’ optimism outright.

“Democrats have been enjoying too much bourbon because their Kentucky 6 wishes are delusional,” said NRCC spokesperson Zach Bannon. “Republicans are poised to keep KY-06 red to retain and expand our majority.”

​Politics

Democrats in competitive primaries keep fighting about corporate PAC money. It has opened up a muddy and sometimes performative debate.

The issue has played out in contested Senate primaries, where Democrats have pledged not to accept corporate PAC money to signal their support for campaign finance reform and show voters that they are not beholden to special interests. Among the Democrats seeking to distinguish themselves: Lt. Gov. Juliana Stratton in Illinois, Lt. Gov. Peggy Flanagan in Minnesota, and both state Sen. Mallory McMorrow and former public health official Abdul El-Sayed in Michigan.

Corporate PACs, which raise money from their employees and distribute it to candidates, usually give in similar amounts to Republicans and Democrats. For several cycles, a growing number of Democratic candidates have sworn off the money, citing the outsized influence of business interests on politics.

But for many, the pledges not to take the money are mostly symbolic. Candidates who aren’t currently in office receive almost no corporate PAC donations anyway, as more than 99 percent of those funds have gone to sitting senators or representatives this cycle, according to a POLITICO analysis of data from the Federal Election Commission. And rejecting one specific type of donation doesn’t actually mean candidates can’t receive support from outside interests — often in much larger amounts than corporate PACs are allowed to send.

Corporate PAC money can also still end up indirectly supporting new candidates: A majority of Democratic senators receive the funding, as do official party groups, both of which donate to and otherwise help Senate hopefuls.

As a result, the escalating debate over corporate PAC money has comparatively little impact on Democratic candidates’ ability to raise money — but it has created an opening for heated attacks from all sides.

Stratton rejected donations from corporate PACs, but millions of dollars in support she has received from a super PAC has been the focus of a flurry of attack ads from Rep. Raja Krishnamoorthi (D-Ill.), one of her top rivals who himself has received millions in super PAC support. Flanagan and McMorrow have both faced criticism for accepting corporate money in past roles, despite their pledges not to do so in their respective Senate races now.

While the push by some Democrats to reject corporate money goes back several cycles, even emerging as a point of contention in the party’s 2020 presidential primary, the focus in Senate primaries is newer.

For Democrats looking for any advantage in crowded races, rejecting the money carries potential electoral benefits. Polling shows the issue resonates not only with a Democratic base interested in money-in-politics reform but also with independent and Republican voters.

“Pledging to forego corporate PAC money is one way that candidates signal to voters that they reject business as usual in Washington and want to work to fix our broken campaign finance system,” said Michael Beckel, director of money in politics reform at Issue One, a nonprofit advocacy group.

Still, “even when a candidate rejects a PAC check, there are still ways for corporate interests to curry favor,” Beckel said.

The debate among Democrats comes at a time when corporate PACs account for a smaller share of funds influencing races. Corporate PACs face strict limits for their political giving, $5,000 per cycle, a number that has not changed in decades, even as individual giving limits are indexed to inflation. Far more funds now flow through super PACs — which candidates are free to criticize but don’t have to reject.

And the questions are unlikely to fade: The Democratic National Committee has sought to explore how it could limit corporate money, along with harder-to-trace “dark money” that flows through nonprofit groups, in the party’s 2028 presidential primary.

“I think it just shows this fundamental shift even inside the Democratic Party, that running on anti-corruption is no longer a niche position,” said Tiffany Mueller, president of End Citizens United, which backs Democrats supportive of campaign finance reform and has, since 2018, had candidates sign pledges that include a promise to reject corporate PAC money.

The group’s pledge this cycle, which includes several money-in-politics reforms, has gotten signers quicker than past pledges, Mueller said.

In Illinois, where early voting is already underway ahead of Tuesday’s primary, Stratton has made rejecting corporate PAC money a key component of her campaign in a three-way primary against Krishnamoorthi and Rep. Robin Kelly. The lieutenant governor, who was endorsed by End Citizens United, accused both opponents of benefiting from a “broken” campaign finance system.

“I’m the only candidate rejecting corporate PAC money, because my campaign is about the people of Illinois, not special interests,” she said in a statement.

Kelly, in an interview, defended her own record of accepting some donations from corporate PACs, saying that the funds over the years supported Democrats and never influenced her voting record. She noted the much greater flow of super PAC money supporting both of her opponents.

“When I came to Congress, I didn’t know my dues were going to be the level that they were. I didn’t know that I was expected to give money to my other colleagues, or people that wanted to be my colleagues,” Kelly said. “And frankly, the money I collect, that’s where a lot of it has gone through the years, paying dues to the DCCC.”

While Stratton has sought to carve out a lane as the reformer, Krishnamoorthi’s campaign has gone after her finances, with ads running on both television and digital accusing her of taking “corporate and MAGA money” and calling attention to a super PAC backing her. Krishnamoorthi’s campaign did not respond to a request for comment.

Stratton has benefited from $11.8 million from a super PAC linked to Illinois Gov. J.B. Pritzker, with additional support from the Democratic Lieutenant Governor’s Association. Meanwhile Fairshake, backed by major cryptocurrency interests, has spent nearly $10 million attacking her to help Krishnamoorthi.

The scrutiny on corporate PAC money in primaries comes as a majority of sitting Democratic senators continue to take those donations for their campaigns and leadership PACs. That includes several senators who have actively been endorsing in the primaries, including Sen. Chris Van Hollen (D-Ct.), who has endorsed Flanagan in Minnesota, and Sen. Martin Heinrich (D-N.M.), who has endorsed both Flanagan and McMorrow.

Corporate PACs can — and do — give larger donations to party committees. That has been a point of conflict in Minnesota, where opponent Rep. Angie Craig has hit Flanagan for corporate PAC donations accepted by the DLGA while she was its chair. The group is now backing her campaign along with Stratton’s.

Flanagan’s campaign has said she did not have sole decision-making power over the DLGA’s donors. In a statement to POLITICO, a spokesperson for Flanagan accused Craig of “trying to distract from the fact that she’s taken millions of dollars from corporations and special interests.”

“Peggy is the only candidate in this race to reject corporate PAC money,” the spokesperson said. Craig’s campaign declined to comment.

The divide extends from safe-seat races to the most competitive. In the Michigan Senate primary, which sets up a must-win open seat for Democrats looking to take back control of the upper chamber, the issue has already arisen in candidate forums. El-Sayed, who previously ran for governor, has sought to distinguish himself on the basis that he has never taken corporate PAC money.

“There’s only one candidate in this race who’s understood corporate money to be the central disease of our politics from day one when they ran in 2018,” said Sophie Pollock, a spokesperson for El-Sayed’s campaign, in a statement.

Rep. Haley Stevens, meanwhile, received donations from corporate PACs as a representative and has continued to for her Senate campaign. Her campaign spokesperson, Arik Wolk, noted she repeatedly voted for campaign finance reform and recently received an “A” grade from End Citizens United on its anti-corruption scorecard.

And although McMorrow previously accepted corporate PAC money for her state legislative campaign and leadership PAC, she has rejected it for her Senate campaign.

“As a first-time candidate, there were people who said, ‘We need to fight like the Republicans fight. If we don’t, we will lose,’” McMorrow said in an interview. “And I’ve learned through my time in the legislature that, you can’t talk out of both sides of your mouth, that people won’t trust you. And also, not only can we fund campaigns without corporate PAC dollars, but frankly, we need to.”

​Politics

Leading Washington strategist Juleanna Glover publicly argued for a third-party presidential candidate halfway through Donald Trump’s first term, calling for a “morally lucid” leader akin to abolitionist Abraham Lincoln.

At the same time, she was privately trading emails with Jeffrey Epstein — a decade after he went to jail on child prostitution charges — to share possible presidential tickets “outside the partisan lanes.”

Glover even offered some “radical combinations” in an August 2018 email to a group of “third party thinkers” she then forwarded to Epstein via his now infamous address jeevacation@gmail.com. Her list of dream tickets mixed and matched figures like former Facebook executive Sheryl Sandberg, former Republican Govs. Larry Hogan of Maryland and Nikki Haley of South Carolina, and Microsoft tycoon Bill Gates, coincidentally an Epstein associate himself.

Glover proposed: “Biden/Romney? Bill Gates/Hogan? Bloomberg/Haley? Howard Schultz/Bob Corker? Sandberg/Kasich?”

Their correspondence about centrist fantasy politics was only a small piece of a professional and political relationship that stretched across more than a year. Their workaday messages about third party campaigns, conversations that could have easily been with a well-regarded opinion columnist, underline the degree to which a large number of influential people treated Epstein as if he was just another rich guy to be courted rather than a convicted sex criminal with a troublesome reputation.

Glover, who has long been a leading Never Trump figure, told POLITICO in an interview that her motivation for engaging with Epstein was solely focused on unearthing any potential information that could sink Trump’s reelection.

Despite that claim, there are no emails between Glover and Epstein that show her soliciting information from him about Trump. While she referred POLITICO to a fellow Never Trumper to corroborate that motivation, a second person involved in some of her interactions with Epstein at the time, said they were not aware of her approach.

And in an interview, Glover acknowledged she had also asked Epstein for help in a business matter in 2017 involving her then-most prominent client, Elon Musk, and Saudi Arabia. In one Tesla-related email, Glover said that if Epstein was advising any sovereign wealth funds wanting to help “a prominent company go private,” she could help. In the second email to Glover, Epstein criticized Musk for not being “fluent” in how to deal with Middle Easterners’ “bluster” and “bloviating bragging” after Saudi funding did not come through.

Glover took a stab at helping reintroduce Epstein to parts of mainstream society and made a brief attempt to fashion him into a champion of democracy, arranging a meeting with the head of the nonprofit group Freedom House in 2017. And it wasn’t just Glover advising Epstein — he also offered suggestions on how to talk to New York Times reporters writing about Musk’s rumored drug use.

Glover’s and Epstein’s relationship encompassed several dozen emails, two in-person meetings and a number of calls, according to a POLITICO review of the Epstein files released by the Department of Justice. Her name returns 191 results in the files, although many mentions are duplicates.

Glover characterized the relationship as a limited series of interactions comprised of 31 emails that she sent him, of which 12 dealt with logistics and 15 regarded Tesla. (The Tesla emails showed that Glover was leveraging the relationship with Epstein to help her client.) She said they had two meetings and three calls. She said the remaining were two emails on third party politics, one on MAGA stalwart Steve Bannon and the last connecting Epstein to a pro-democracy nonprofit. Glover said that he was never a client and she “never took anything of value from him.”

Their dynamic, catalogued here in full for the first time, further demonstrates the expansive reach of the late sex offender’s connections across the political spectrum. His Rolodex ranged from moderate former Republicans like Glover to Bannon and giants of the American left like Noam Chomsky.

Glover, a former aide in the George W. Bush White House and an adviser to John McCain’s presidential campaign, had by 2017 largely moved on from professional electoral politics and built a thriving practice as an adviser to executives and corporations seeking to navigate the media landscape.

Her townhouse in Kalorama is a gathering place for a wide array of D.C. operators, think tankers, campaign funders and journalists. She has built goodwill across the town and a thriving personal network in part with her willingness to host book parties, new job celebrations and more: Indeed — she was a co-host of an engagement party in 2023 for the author of this article, and has thrown book parties for multiple past and present POLITICO reporters.

Glover consulted for Axel Springer, POLITICO’s owner, several years ago, according to a company spokesperson.

‘Captive’ to Elon Musk

Glover came to know Epstein through another type of fixer who was also advising him on PR strategies. The journalist Michael Wolff, a shared acquaintance of the two, first mentioned Glover to Epstein in March 2017 as she was consulting for Musk.

“I rolled the dice when Michael Wolff asked me to meet with Epstein against the backdrop of Epstein talking publicly about Trump,” she said in a statement. “My interactions with Epstein were in service to that objective; not to help him in any way or improve his image. Wolff was seemingly positioning me as someone smart enough for him to take advice from.

“To wit, I repeatedly steered Epstein to talk to top investigative journalists including Jim Stewart of the NY Times and Epstein eventually did so, ultimately talking to Stewart about writing his book. I never knew what Epstein was planning to say, but a Pulitzer Prize-winning journalist almost found out,” she said, referring to Stewart.

At the time of her interactions with Epstein about Stewart, Musk’s move to try to take Tesla private led to a Securities and Exchange Commission probe and rumors of drug use. He needed all the communications help he could get.

“[T]here’s a Washington PR type named Juleanna Glover with whom you might want to chat,” Wolff wrote to Epstein that spring. “Elon Musk basically owns her now and I’m not sure she can take on other clients, but she will have a valuable perspective on how you get to where you want to be.”

Two months later with the subject line “More PR,” Wolff reminded Epstein that they had spoken about Glover, reupping the Musk connection.

“She’s captive to him, so not hireable. But she’s exceedingly smart and well connected and has interesting things to say,” he wrote. “She can offer an extremely informed overview on how to think about larger steps. Not so much about the trial per se, but going forward. Anyway she is in NYC on Thursday with some time if you wanted me to arrange a meeting.”

Within an hour, Epstein wrote back, “Yes please.”

Three days later, Epstein, Glover and Wolff had lunch together on a day that Epstein was set to have breakfast with private equity investor Leon Black and dinner with director Woody Allen and his wife Soon Yi Previn, according to his schedule. (Black has been accused of sexual assault by two women but has denied all allegations.)

Wolff has written books critical of the president and in 2016 even told Epstein “you’re the Trump bullet” to stop his rise given their former relationship. Last November, Wolff posted an Instagram video in which he said, “These two men, Jeffrey Epstein and Donald Trump, had the closest of relationships for more than a decade.”

Trump has said he wasn’t involved in any of Epstein’s criminal activity and that they had a falling out years ago. Epstein was once a frequent visitor at Mar-a-Lago and court records indicate that Trump flew at least once on one of Epstein’s planes and his phone numbers were in Epstein’s directory. There’s no evidence to suggest Trump took part in Epstein’s trafficking operation.

Wolff said in a statement that he worked on an effort with Glover to get Trump to publicly respond to questions about his relationship with Epstein during the 2016 presidential campaign. Glover said that Wolff had called her in the fall of 2015 to try to have reporters ask Trump about Epstein. That’s why Wolff emailed Epstein that year regarding how Trump might handle questions about their shared history.

“In 2017, I encouraged Juleanna to see Epstein in the hope that she might help convince him to go public about what he knew about Trump,” he said. “I believe she suggested to Epstein that Jim Stewart at the Times would be receptive.”

Glover referred POLITICO to an anti-Trump political consultant, Rick Wilson, with whom she had been in touch about Epstein in 2015, years before her correspondence with Epstein began.

Wilson told POLITICO that he and Glover had a phone call in the fall of 2015 to try to figure out if Epstein had any dirt on Trump.

“She’s a great communicator, and that’s why people seek her out, and that’s why she was so valuable in this anti-Trump fight at the time,” he said. “She was definitely in the pursuit of trying to stop Trump.”

In the summer of 2018 she asked Epstein about Stewart, who was writing a piece on Musk.

“Do you like Jim Stewart?” she wrote to Epstein in August 2018. “Will send him to you for deep backgound [sic] convo if you like? But only if you like.”

“[N]o thanks,” Epstein replied. “I live in dark background.”

During several days in August, the two exchanged emails and calls about Musk, who was looking for wealthy investors to buy out shareholders.

“If you are advising re: sovereign wealth funds looking to help a prominent company go private, let me know if I can help w any approp additional information,” she wrote Epstein on Aug. 12.

“Clever,” he replied. She also offered a primer on how Tesla’s Autopilot worked.

Epstein passed along names of potential candidates to join Tesla’s board, suggesting former Treasury Secretary Larry Summers, former Obama White House counsel Kathy Ruemmler and Margaret Thatcher, not realizing she had been dead for five years. (Summers and Ruemmler have apologized for their connections to Epstein and left their jobs after their ties to him were highlighted in the files.)

Epstein also offered to “help shape your story” and gave Glover advice on how Musk should talk on the record to Stewart or then-Times reporter Landon Thomas Jr. about the situation.

“Will try,” Glover replied.

Two days after Epstein’s death, Stewart wrote a column recounting a meeting he had with Epstein in which he claimed to know information about wealthy and famous people that was “potentially damaging or embarrassing, including details about their supposed sexual proclivities and recreational drug use.”

Thomas Jr. left the Times in 2019 after he solicited a major charitable gift from Epstein, who’d been a source, according to an investigation by NPR and a statement the publication made to the New York Post. Thomas Jr. declined to comment to NPR and didn’t respond to a request for comment from POLITICO.

Stewart said in a statement that he wasn’t aware at the time of any relationship between Glover and Epstein and didn’t know about anything Epstein might have told her.

“As I would with any potential source, I reached out to Epstein because I’d heard he was recruiting board members for Tesla at the behest of Musk,” he said. “Epstein wanted to meet in person, so I went to his townhouse. (I subsequently wrote about that encounter.) I don’t recall using anything Epstein had to say in any story about Musk. He certainly didn’t ‘shape’ any story I was involved in.”

Times spokesperson Danielle Rhoades-Ha said in a statement that Thomas Jr. hadn’t worked at the Times since 2019 “after editors discovered his failure to abide by our ethical standards. Times editors were not aware at the time of Thomas’s now-public emails with Epstein.”

Referring to Musk, Epstein told her that he only said “great things about your boy” while sharing that “some of the papers are looking into whether you [sic] boy was on drugs.” He then asked Glover if there are “different colors of cocaine. ? ! ectasy [sic]. (I know zero about drugs).”

“Nothing to it,” she replied. “He barely even drinks.” She acknowledged three days later, “Oh and re burning man, he hasn’t gone in years but may go w his musician girlfriend the last weekend in aug – that is the best the rumor mongers can do.”

After the Times published the interview, Elon Musk Details ‘Excruciating’ Personal Toll of Tesla Turmoil, Epstein emailed Glover, saying “good work – interview apart from the one short seller comment. :)”

Glover responded: “Glad you think it improves situation.”

The exchanges about Musk show how their relationship was a give-and-take compared to a more formal adviser-client set up with Epstein giving positive feedback to one of the nation’s leading communications strategists on her own media approach. At the same time, Glover also steadfastly defended her client, insisting he didn’t do drugs less than a month before he smoked marijuana live on The Joe Rogan Experience.

Glover said that her interactions with Epstein about Musk came during a tense time as Tesla’s leadership was pushing hard to take the company private, which Musk had announced the Saudis and Crown Prince Mohammed bin Salman were key to getting done.

“Epstein had bragged that he was close to MBS, so I reached out,” she told POLITICO. “Musk was unaware that I’d done so. I shared publicly available information about the company, with the intent that Epstein would advise the Saudis to hold steady on their commitment to Musk to take the company private. I was trying to encourage him to weigh in with the Saudis to keep their word to Musk. I do not believe he was in any way useful to this effort as there are no known communications with MBS in the DOJ files.”

Musk didn’t respond to requests for comment.

An attempt at a pro-democracy rehabilitation

Glover’s firm Ridgely Walsh emphasizes “bespoke public affairs services” and the DOJ files reveal the kind of strategic matchmaking services she might offer clients. For Epstein, who needed to burnish his image, she found an advocacy group in need of funding.

After their first lunch meeting in May 2017, Epstein thanked Glover for her time and said he was happy to meet the leadership of the democracy nonprofit Freedom House as he tried to overhaul his public reputation after he pleaded guilty in 2008 to soliciting prostitution from a minor and was sentenced to 18 months in jail. (He served 13 months on a work release program that allowed him to go to his office during most days.)

“The pro- deomcracy [sic] funding is a good idea, no matter what positive fallout it may have on me personally,” he wrote.

He also invited Glover and a guest to see the Tony-award winning play Oslo, in which he bragged that he had bought out the entire Vivian Beaumont Theater at Lincoln Center so that many U.N. diplomats could attend. “[Y]ou would be part of the private gatherings. Many interesting people will attend,” he noted.

Glover doesn’t appear to have replied to Epstein’s invitation but seven weeks later she told Epstein she had secured a date for Michael Abramowitz, the then-head of Freedom House, to come see him. They were all supposed to meet in person on July 24, but Epstein ended up being out of town so the three joined a call. Glover, who has long worked for international dissidents of various stripes, connected the two via email after the call with Abramowitz responding, “nice to meet you. Talk soon I hope.”

A month later, Abramowitz emailed Epstein, saying he hoped he had a good summer and had enjoyed talking to him. While he sent four attachments about the organization, Epstein had the brusque reply “thx” with a link to an article on HuffPost promoting his work funding scientists. (The articleno longer appears on HuffPost.)

The pair ups didn’t always work, although for Freedom House the mismatch turned out to be a positive. Numerous politicians have had to give away Epstein donations to charitable causes and other figures associated with the late sex offender have lost their jobs or resigned from posts.

Freedom House referred a request for comment to Abramowitz.

“I was asked to have a conversation with him about philanthropy,” Abramowitz said in a statement. “It was a brief phone call, and Freedom House never accepted money from him.”

Glover said she connected Epstein to Abramowitz because Epstein was interested in funding nonprofits. Glover and her firm have experience working with pro-democracy efforts including work on the Magnitsky Act, much of which she does pro-bono. (The Magnitsky Act allows the U.S. government to punish foreign officials for human rights abuses.)

“We do much work in the pro-democracy space, so I asked Freedom House to talk to Epstein about what overseas nonprofits might prove to be the most effective in supporting democracy efforts in Russia and Eastern Europe (at that time Russians were in the streets in large numbers protesting Putin),” she said.

“There was also growing awareness about Putin directing interference in the U.S. 2016 election and the U.S. was certainly not going to step up to support free elections given Trump’s growing closeness to Putin so I suggested Epstein do it,” Glover said.

“I suspected these foreign groups would welcome his money in their vital, but cash-strapped work,” she added. “I have apologized to the good leaders of Freedom House for connecting this storied institution to this monster. Nothing came of that conversation. Epstein of course lied about his intent and/or ability to marshal money.”

A warning about Steve Bannon

There were tensions embedded in Epstein’s relationship with Glover, a classic establishment GOP operator, and his similarly newfound friendship with Bannon, the conservative firebrand who was separately giving him strategic advice. It’s an illustration of Epstein’s success at cracking the political world that he was able to maintain relations with both of them.

In their 2018 correspondence about unconventional presidential tickets, Epstein took care to write “(not bannon)” when telling Glover that his other “friends with great knowledge of the system” thought the third party idea was “brilliant.”

Glover replied back with a link to a New York Times op-ed she authored about third parties “that says something of the same.”

In December 2018, Epstein replied back to a blast from Glover sharing a POLITICO Magazine op-ed she had written about how Joe Biden should run on a unity ticket with Mitt Romney.

“[Y]ou are right of course,” Epstein wrote.

Months earlier, Glover passed along a request by the BBC to put the outlet in touch with Wolff about Epstein. Wolff forwarded it to Epstein, who told him to get more information on the matter.

“On the job,” Wolff replied.

Glover emailed him to say she was going to be in New York City the next day and wanted to check in. Epstein wrote back that he “would have loved to however i am in the caribean [sic] please try again next time.”

“Will do,” Glover replied. “Take care.”

In April, Glover checked in again to ask if Epstein would be free in a few days in New York City, adding “Hope all is well.” He told her he was not in town that day. But the two met up in July after Glover emailed him again asking if he was in Manhattan, adding “Hope all is great.”

On her way to the meeting at his Upper East Side mansion, she apologized for being a few minutes late, saying “I am so sorry!”

Among the topics of discussion at their meeting was Epstein’s dealings with Bannon.

“On reflection, I don’t think any good can come from Steve being in your sphere,” Glover wrote to Epstein the next day. “I have only met him once but there is a malice and manipulative vengeful nature there that can only cause you harm. He will use his access to you to leverage something unwelcome – not sure what, but he’s conjuring dark forces and access to you is only energizing him.”

Epstein thanked her, and added, “I will take advice.” (Despite telling her that, hecontinued to talk to Bannon up until his arrest the next year on new sex trafficking charges and sat down for interviews with Bannon for a documentary he was making.)

Asked why she had warned Epstein about Bannon, Glover told POLITICO that Epstein had mentioned to her he was seeing Bannon later in the day during their July 2018 meeting. “I warned Epstein away from Bannon, as I thought Bannon would block Epstein from saying what he knew about Trump,” she said.

A spokesperson for Bannon declined to comment.

The last instance of Glover in the files is in March 2019 when Epstein emailed hera link to a letter to the editor of the Times that his four lawyers had written defending Epstein and saying “the number of young women involved in the investigation has been vastly exaggerated.” It continued that the earlier “case lacked the credible and compelling proof that is required by federal criminal statutes.”

She did not reply.

He died by suicide in his New York jail cell five months later on Aug. 10, 2019.

​Politics