Boris Epshteyn: Trump's "psychiatrist" and counsel

"He's like my psychiatrist," Trump has joked, referencing how frequently he talks to Epshteyn — who typically offers such enthusiastic support that it's like therapy for the president.

• In Trump's fractious political world, though, such presidential praise draws criticism, including from within.
• "He's 100% hype man and cheering section for POTUS," one adviser said. "It's sometimes a bit much."

Driving the news: Though Epshteyn operates out of the spotlight, he was seen on national TV Monday night, standing in the same shot as the president at Game 3 of the NBA Finals in Madison Square Garden.

• Last week, Epshteyn's role in the settlement that created the highly controversial $1.8 billion "anti-weaponization" fund was detailed in the New York Times and Wall Street Journal. The administration scrapped the idea amid a bipartisan outcry in Congress.

Zoom in: As Trump's top personal attorney, Epshteyn has overseen a wave of unprecedented civil litigation from a president against the news media and social media companies.

• Trump has won or forced settlements with ABC ($16 million), CBS ($16 million, plus public service announcements), Meta ($25 million), Google ($22 million) and X ($10 million).
• Other Trump media targets still in litigation: BBC, CNN, The New York Times, The Wall Street Journal and even the Pulitzer Committee.

The big picture: Epshteyn became a force in Trumpworld by assembling the legal team and charting the risky strategy that paid off during the 2024 election cycle, when Trump faced four criminal cases and two civil ones.

• Channeling his client, Epshteyn made brinksmanship the default tactic, fighting on every front, appealing everything possible (winning a landmark Supreme Court presidential immunity declaration) and raising the political pressure on judges and prosecutors as cases unfolded in the heat of an election.
• "Boris delivered in the crucible of battle where either Trump was going to be in prison or be president," said Steve Bannon, influential MAGA podcaster and first-term Trump official. "Boris was the guy who got it done."
• "He's the president's fixer," said a frequent White House visitor.

Between the lines: Epshteyn's role extends beyond the courtroom. In April, he was named chair of Trump Media. Donald Trump Jr. serves as director.

• Epshteyn has significant influence in the Justice Department, Trump advisers say, because of his close relationship with acting Attorney General Todd Blanche, who replaced Pam Bondi.
• Epshteyn is in the Oval Office about once a week, a White House official said, and is "constantly" on the phone with Trump in between.
• Pointing to the needless political distraction of the aborted anti-weaponization fund, a Trump political adviser was less effusive about Epshteyn:
• "He's the keeper of dog-sh*t ideas," the adviser said. "And he has only gotten more powerful, maybe one of the five most powerful people around the president."

The intrigue: From custom-made suits to his Bentley to his penchant for taking meetings at a classic D.C. steakhouse, Epshteyn's wealth has been a constant source of speculation in Trump's circles.

• A friend of Epshteyn countered that he was successful before his current role, and bought his car six years ago. "Boris has lived the exact same lifestyle for the past decade. Any suggestion to the contrary is founded on baseless rumors and innuendo," he said.
• "I've tried to cut him in on a side deal for pardon work. And Boris said no. He's ethical," said one Trump insider and attorney who successfully persuaded the president to grant his client clemency.

During the transition, another team of Trump attorneys conducted an internal investigation to determine if Epshteyn had parlayed his connections to Trump, which Epshteyn denied.

• A Trump spokesman at the time characterized the inquiry as a "review" and said it had been settled internally. Trump kept Epshteyn.
• During the transition, Axios reported, Epshteyn also clashed with billionaire Elon Musk. Though Musk's star was ascendant in Trump's orbit, the president kept Epshteyn on, a sign of his staying power.

The backstory: Epshteyn, a former adviser to John McCain's presidential campaign in 2008, entered Trump's operation a decade ago when the then-candidate saw Epshteyn voicing support for his campaign on cable TV.

• When Trump's top legal counsel, Michael Cohen, was indicted in 2017 and had a falling out with Trump, Epshteyn slowly began filling his shoes.
• White House communications director Steven Cheung cited Epshteyn's pugnacity, longevity and loyalty, calling him "an original" in Trump's political circle.

In 2021, as Trump plotted his return to the White House at a time when many in his own party wanted him gone after the Jan. 6 Capitol riot, Epshteyn stuck by Trump's side along with Susie Wiles. She became Trump's top political adviser as Epshteyn handled legal affairs.

• Epshteyn became Trump's top counsel after the National Archives and President Biden's DOJ began criminally investigating Trump in the classified documents case.
• As the criminal cases grew, they became a potent weapon for Trump on the campaign trail. He argued that the prosecutions were political persecutions. It helped him win the GOP primary and galvanized his voters in the 2024 general election.
• Throughout, Epshteyn pushed Trump to fight the cases, make no compromise and take everything to trial, which others advised against.
• "What Boris advised and what the president did was frankly insane, completely risky," said a Trump adviser. "But it worked. That's why Boris is where he is."