In a bombshell internal email from a federal prosecutor in January 2020—now exposed in the newly unsealed Epstein files—investigators learned Donald Trump flew on Jeffrey Epstein’s notorious private jet far more times than previously known, at least eight trips in the 1990s, including four alongside Ghislaine Maxwell and one alone with Epstein and a mysterious redacted 20-year-old woman.T

What Revealing Exchanges Surface in the Newly Unsealed Jeffrey Epstein Emails That Repeatedly Reference Donald Trump, Casting Fresh Light on Their Long and Complicated Relationship?

The latest unsealed Jeffrey Epstein emails, released in November and December 2025 by House Oversight Democrats and the Justice Department, contain dozens of references to Donald Trump, illuminating the depth and complexity of their association spanning decades. Drawn from over 20,000 pages subpoenaed from Epstein’s estate, these messages—primarily from Epstein to Ghislaine Maxwell and journalist Michael Wolff—paint a picture of lingering proximity even after their public fallout.

In a 2011 email to Maxwell, Epstein described Trump as “the dog that hasn’t barked,” noting that a trafficking victim “spent hours at my house with him” yet Trump never mentioned it publicly. Another 2019 message to Wolff asserted Trump “knew about the girls” and had asked Maxwell to “stop,” apparently referencing recruitment at Mar-a-Lago. Wolff, in a 2015 exchange, suggested Epstein leverage their history for “valuable PR and political currency” if Trump distanced himself.

Separate DOJ releases in December 2025 revealed internal prosecutorial notes on flight logs, showing Trump aboard Epstein’s jet at least eight times in the 1990s—far more than previously reported—including four with Maxwell and one solely with Epstein and a redacted 20-year-old woman. These predate Trump’s claimed 2004-2007 ban of Epstein from Mar-a-Lago over alleged misconduct.

Trump has denied wrongdoing or knowledge of Epstein’s crimes, emphasizing their estrangement and his role in Epstein’s 2019 arrest. The White House dismissed selective releases as attempts to “smear” him, while the DOJ flagged some claims as “untrue and sensationalist.” No evidence implicates Trump in illegal acts, but the emails underscore Epstein’s perception of influence and silence.

As over a million additional documents await review, these exchanges fuel bipartisan demands for transparency, highlighting how elite ties persisted amid Epstein’s predation and raising enduring questions about accountability in circles of power.