High above the Atlantic, a private Boeing 727 sliced through the clouds in early 2006, carrying a rising Wall Street executive who would one day lead the U.S. Navy—unaware, friends say, whose jet he had boarded until it was too late.
In the massive 2026 Epstein Files disclosures—millions of pages from the Justice Department—flight manifests confirm Navy Secretary John Phelan flew round-trip New York to London twice on Jeffrey Epstein’s infamous plane: outbound February 27 and return March 3, 2006. Listed alongside Epstein himself and others (including model scout Jean-Luc Brunel), Phelan was then at MSD Capital; a close friend later told reporters the ride was arranged by Bear Stearns CEO Jimmy Cayne, with Phelan never speaking to Epstein again.
No wrongdoing has been alleged against Phelan, yet these long-buried logs now cast a stark shadow over his ascent to one of America’s highest defense posts.
What other names—and stories—still wait in those redacted lines?
High above the Atlantic, a private Boeing 727 sliced through the clouds in early 2006, carrying a rising Wall Street executive who would one day lead the U.S. Navy—unaware, friends say, whose jet he had boarded until it was too late.
In the massive 2026 Epstein Files disclosures—millions of pages from the Justice Department released in late January—flight manifests confirm that John Phelan, now Secretary of the Navy, flew round-trip New York to London twice on Jeffrey Epstein’s infamous Boeing 727, known as the “Lolita Express.” The outbound leg departed New York’s JFK Airport on February 27, 2006, bound for London Luton, with the return from London to New York on March 3, 2006. Phelan is listed among passengers including Epstein himself and French modeling agent Jean-Luc Brunel—an Epstein associate later accused of sexual assault and rape of minors before his 2022 death in custody. Six other names on the March 3 manifest remain redacted in public versions.
At the time, Phelan was a senior executive at MSD Capital, the private investment firm managing billionaire Michael Dell’s fortune. Sources close to Phelan, speaking to outlets like CNN after the February 2026 revelations, described the flights as arranged by the late Bear Stearns CEO Jimmy Cayne, not directly by Epstein. They insist Phelan did not know the plane belonged to Epstein until boarding or shortly after, had minimal to no interaction with him during the trip, and never spoke to or associated with Epstein again. Phelan declined direct comment through a Navy spokesperson following the document release.
No allegations of wrongdoing have surfaced against Phelan in the files or related investigations. The flights occurred well before Epstein’s 2008 Florida plea deal for procuring a minor for prostitution, during a period when Epstein’s private jet ferried numerous high-profile figures in finance, science, and entertainment under the guise of legitimate networking and philanthropy.
The disclosures have nevertheless cast a stark shadow over Phelan’s ascent to one of America’s highest defense posts. Appointed by President Trump in 2024 as the 79th Secretary of the Navy—a role overseeing naval operations, shipbuilding, and policy—Phelan is a prominent Republican donor, art collector, and Trump ally who hosted fundraisers and raised millions for campaigns. The Epstein connection joins a pattern in the 2026 files of Trump administration figures with prior, often incidental ties to the financier, including Commerce Secretary Howard Lutnick and others.
While the manifests show no evidence of illicit activity on these transatlantic legs—no island visits, no reported presence of victims—the episode fuels broader scrutiny: How did Epstein’s network extend into Wall Street circles? Why were such rides accepted amid emerging whispers about his behavior? And what details hide in the remaining redactions or unreleased portions of the vast trove?
As analysis continues, Phelan’s case highlights the enduring ripple effects of Epstein’s elite associations—connections that, even if fleeting and unknowing, resurface decades later to challenge public trust in those who ascend to power. No proof links Phelan to Epstein’s crimes, but the flight logs serve as a reminder of how proximity to the disgraced financier can linger as a political liability in an era of forced transparency.
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