Boris Epshteyn sits in Oval Office meetings so quietly that some attendees don't realize he's there. Trump puts him on speakerphone without warning the room. He speaks with the president so frequently that Trump has joked he's "like my psychiatrist," offering the kind of unflinching support that functions as presidential therapy.
In a White House where proximity equals power, Epshteyn has become one of the most influential figures in Washington. He is not just present at the table. Trump actually listens to him.
The president's senior personal counsel operates almost entirely out of public view, but his fingerprints are on the most aggressive legal offensive any sitting president has mounted against the media and tech companies. Trump has extracted settlements or wins totaling at least $89 million from ABC, CBS, Meta, Google, and X. The BBC, CNN, The New York Times, The Wall Street Journal, and even the Pulitzer Committee remain in active litigation.
Beyond the courtroom wins, Epshteyn shaped Trump Media as its chairman and wields significant influence over the Justice Department through his close relationship with acting Attorney General Todd Blanche. He appears in the Oval Office roughly once weekly and is "constantly" on the phone with Trump otherwise.
But his elevation comes with criticism even from within Trump's own camp. One adviser described him bluntly: "He's 100% hype man and cheering section for POTUS. It's sometimes a bit much." Another Trump political operative called him "the keeper of dog-sh*t ideas" and worried that his power was growing unchecked.
Epshteyn's rise accelerated during the 2024 election cycle when Trump faced four criminal cases and two civil ones. Rather than seek settlements or negotiate, Epshteyn charted a scorched-earth strategy: fight on every front, appeal everything possible, and flood the zone with political pressure on judges and prosecutors. When Trump won a landmark Supreme Court presidential immunity ruling, it validated the gamble.
"Boris delivered in the crucible of battle where either Trump was going to be in prison or be president," said Steve Bannon, the influential MAGA podcaster. "Boris was the guy who got it done."
What made Epshteyn's approach work was its sheer audacity. "What Boris advised and what the president did was frankly insane, completely risky," one Trump adviser acknowledged. "But it worked. That's why Boris is where he is."
His path to Trump's inner circle began a decade ago when Trump saw Epshteyn defending him on cable television. Epshteyn, a former McCain campaign adviser, gradually filled the void left after Michael Cohen's 2017 indictment. When Trump's criminal troubles accelerated under the Biden administration, Epshteyn became his primary legal strategist.
He remained loyal even when others fled. In 2021, as Trump faced party abandonment following January 6, Epshteyn stood firm alongside political adviser Susie Wiles while much of the Republican establishment turned away.
The $1.8 billion "anti-weaponization" fund that Epshteyn helped negotiate last week offers a window into the criticism he faces. The controversial settlement, which Trump's administration subsequently scrapped after bipartisan congressional outcry, drew unflattering comparisons to his more successful litigation work.
Questions about Epshteyn's enrichment have circulated for years. His custom-made suits, Bentley, and preference for exclusive steakhouses fuel speculation in Trump circles about his finances. A friend defended him, noting he had already accumulated wealth before joining Trump and purchased his car six years ago. "Boris has lived the exact same lifestyle for the past decade," the friend said. "Any suggestion to the contrary is founded on baseless rumors and innuendo."
An internal investigation during the transition examined whether Epshteyn had monetized his Trump access through pardon work or side deals. Trump's team settled the matter internally and kept Epshteyn on the payroll despite the inquiry.
Even Elon Musk's rising star in Trump's orbit did not dislodge him. Though the billionaire clashed with Epshteyn during the transition and his influence with Trump surged, the president retained his counsel. That decision itself signals something about how firmly Epshteyn has anchored himself.
White House communications director Steven Cheung described Epshteyn as "an original" in Trump's circle, praising his pugnacity, longevity, and loyalty. One Trump insider and attorney who watched Epshteyn refuse a lucrative pardon scheme offered by a fellow Trump operative offered his own assessment of Epshteyn's character: "He's ethical."
The influence is real, and for now it appears durable. Trump listens when Epshteyn talks, and in a fractious administration where egos constantly collide, that trust may be worth more than any title.
Author James Rodriguez: "Epshteyn's ascent tells you everything about how Trump operates: he rewards loyalty and ruthlessness above all else, even when the strategy seems insane to everyone watching."
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