The Justice Department’s latest Epstein document dump is resurfacing uncomfortable connections—putting two more senior figures in President Donald Trump’s orbit squarely in the frame.
Last Friday, the Department of Justice released more than 3 million pages tied to convicted sex offender Jeffrey Epstein, reigniting scrutiny of the powerful figures who crossed paths with him over the years—including several members of Trump’s inner circle.
Among those named in the latest tranche are Secretary of the Navy John Phelan and Ben Black, Trump’s personal pick to lead the U.S. International Development Finance Corporation.
Black, a financier and son of billionaire Apollo Global Management founder Leon Black, was quietly sworn in last December after a narrow 51–47 Senate confirmation vote. The ceremony took place just weeks before the House Oversight Committee released another trove of Epstein-related records.
One document reveals an email exchange between Lesley Groff, Epstein’s longtime executive assistant, and Ben Black and his brother Joshua. The subject line was bluntly titled “Jeffrey Epstein.”
In the message, Groff described Epstein’s interest in commissioning a portrait of the brothers as a gift for their father. “Jeffrey has co-signed an artist at the New York Academy of Art,” she wrote, adding that Epstein hoped the brothers would be open to sitting for the piece. Groff noted that an associate had previously met the artist and suggested the brothers “may have seen the finished work.”
The email also explained that each brother would need to meet the artist at least once, before closing with a polite prompt: “Please let me know if you are interested.”
There is no indication in the file that the portrait was ever commissioned—or that either brother accepted the offer. But the correspondence underscores Epstein’s familiarity with the family.
That connection is not new. Leon Black, Ben’s father, has long faced scrutiny over his ties to Epstein. The billionaire previously acknowledged paying Epstein roughly $170 million for what he described as tax and estate planning services.
While Leon has denied any knowledge of Epstein’s sex trafficking operation, a 2024 settlement with the U.S. Virgin Islands attorney general concluded that some of the funds paid to Epstein were used to “fund [Epstein’s] operations.”
Leon has also moved in Trump-adjacent circles, drawing congressional scrutiny in 2018 during investigations into foreign influence surrounding the 2016 election.
The Daily Beast has reached out to Ben Black through the U.S. International Development Finance Corporation for comment.
Another newly released file places Phelan aboard Epstein’s private plane in 2006. A flight manifest shows Phelan listed among passengers traveling from London to New York on Epstein’s Boeing 727—often referred to as the “Lolita Express.”
Six names remain redacted in the file. One of the visible names listed on the flight document is Jean-Luc Brunel, the French modeling agent later accused of raping minors and trafficking young women. Brunel died in a French prison cell in 2022 while awaiting trial.
A source close to Phelan confirmed to CNN that he was on the flight but said he did not know it was Epstein’s plane until he arrived. The source said Phelan’s interaction with Epstein was virtually nonexistent and described the flight as the only time the two ever crossed paths. According to the source, Phelan was invited aboard by the late Bear Stearns CEO Jimmy Cayne, not Epstein himself.
Phelan, a major Republican donor, has been a consistent Trump ally. He helped raise millions for Trump’s campaigns and hosted a high-dollar fundraiser for the then-president-elect ahead of the 2024 election.
White House officials have maintained that Trump does not appear in the newly released DOJ materials. However, the latest dump has surfaced the president’s name in a litany of files, including a complaint that alleged Trump engaged in oral sex with a minor.
The Daily Beast has reached out to both the White House and Phelan for comment.
