The relationship between former President Donald J. Trump and the late financier Jeffrey Epstein has again erupted into public scrutiny following a Wall Street Journal report alleging that Trump sent Epstein a sexually suggestive letter. According to the report, the note reportedly appeared in a leather-bound scrapbook allegedly compiled by Ghislaine Maxwell to mark Epstein’s 50th birthday in 2003. The note, reportedly in a scrapbook compiled by Ghislaine Maxwell to mark Epstein’s 50th birthday in 2003, featured a typewritten message over a naked woman’s outline, referencing shared secrets and signed with a squiggly “Donald” (Wall Street Journal, July 17, 2025)
Trump has strongly denied the allegation, calling the document a fabrication. He has since filed a $10 billion defamation lawsuit against the Journal, its publisher Dow Jones, parent company News Corp, its executive leadership, including Robert Thomson, and reporters Khadeeja Safdar and Joe Palazzolo. Trump announced the lawsuit on his social media platform, calling the story “totally fake,” insisting he “never wrote a picture,” and denouncing it as an attempt to revive controversies about his past ties to Epstein, connections he has repeatedly downplayed.
The report has intensified public attention on the long-running Epstein scandal. Epstein was alleged to have sexually exploited and trafficked underage girls while socialising with billionaires, royals, and politicians. Though his 2019 death in a New York jail was ruled a suicide, the circumstances surrounding it sparked widespread speculation and conspiracy theories.
Epstein’s transformation from financier to convicted sex offender with powerful connections remains clouded in mystery. His ties to former President Bill Clinton, Prince Andrew, and Trump have been dissected in court documents, media investigations, and congressional inquiries (The New York Times, Understanding the Epstein Saga).
From Palm Beach to Fallout
Trump’s relationship with Epstein began in the late 1980s or early 1990s when both men were prominent figures in Palm Beach, Florida. Trump had purchased Mar-a-Lago and was converting it into a private club, while Epstein was establishing himself in the area, purchasing a mansion nearby. They were reportedly often seen at social events in Palm Beach and Manhattan in the early 1990s (The New York Times, A Timeline of What We Know About Trump and Epstein).
In 1992, NBC filmed a segment at a Trump-hosted party at Mar-a-Lago where Trump and Epstein were captured laughing and gesturing toward young women, reportedly NFL cheerleaders. After Epstein’s 2019 arrest, the footage became a visual anchor for speculation about their friendship.
In a 2002 New York Magazine profile, Trump called Epstein “a terrific guy,” adding, “He’s a lot of fun to be with. It is even said that he likes beautiful women as much as I do, and many of them are on the younger side.” While unremarkable at the time, the comment later drew darker scrutiny.
Flight records revealed that Trump reportedly flew on Epstein’s private jet several times between 1993 and 1997, mostly on short domestic routes (NYT, Timeline). No records link Trump to Epstein’s island or the international flights that were later investigated. No direct evidence has tied Trump to Epstein’s criminal conduct.
In 2000, Epstein’s connection to Mar-a-Lago took a troubling turn. Virginia Giuffre, then a teenage locker room attendant at the club, was allegedly recruited by Ghislaine Maxwell under the guise of learning massage therapy (NYT, Timeline). Giuffre later became one of Epstein’s accusers, alleging years of abuse. She never accused Trump of misconduct and, according to Miami Herald interviews and court documents, stated that he never behaved inappropriately. Still, the fact that a victim was allegedly recruited at Mar-a-Lago remains a troubling footnote. Giuffre died by suicide in April 2025. Authorities ruled out foul play (NYT, Timeline).
A 2018 Miami Herald investigation exposed the scale of Epstein’s crimes, revealing that he allegedly abused about 80 women between 2001 and 2005. In 2025, the Justice Department found no proof Epstein had blackmailed powerful people, declaring in a July memo that no “client list” existed (NYT, Understanding the Epstein Saga). The findings reportedly fuelled public scepticism and debate over transparency.
By 2004, Trump's and Epstein’s relationship appeared to be deteriorating. Both men reportedly competed to purchase the Palm Beach estate Maison de L’Amitié. Trump outbid Epstein, later selling the property for nearly $100 million. Their relationship notably soured after the property dispute, and although Trump has claimed Epstein was later banned from Mar-a-Lago, the reasons for the alleged ban remain unverified (NYT, Timeline).
Plea Deals and Public Denials
Epstein’s first arrest came in 2005 following a police investigation in Florida. In 2008, he struck a plea deal, pleading guilty to lesser state charges and serving 13 months under a work-release arrangement. The deal shielded alleged co-conspirators and was approved by then–U.S. Attorney Alexander Acosta, who later became Trump’s Secretary of Labour. Acosta resigned in 2019 amid renewed scrutiny of the deal (NYT, Understanding the Epstein Saga).
When Epstein was arrested again in July 2019 on new federal sex trafficking charges, Trump distanced himself. “I knew him like everybody in Palm Beach knew him,” he said. “I was not a fan.” Epstein died in custody weeks later, with the death ruled a suicide. Guards reportedly failed to perform scheduled checks, and cameras reportedly malfunctioned. An autopsy confirmed suicide by hanging, but the circumstances reportedly sparked suspicions.
In 2025, the Justice Department released a memo reaffirming the suicide ruling and stating that no comprehensive “client list” had been found. The memo dismissed theories of foul play as unsupported (NYT, Understanding the Epstein Saga). Still, public trust remains strained. The DOJ had earlier promised to release flight logs and sealed materials but later reversed course, drawing criticism from across the political spectrum.
A Letter, A Lawsuit, and Lingering Doubts
In the wake of the Wall Street Journal report, Trump called for full transparency. Florida Attorney General Pam Bondi filed a motion in federal court in Manhattan seeking the unsealing of grand jury materials related to both the Epstein and Maxwell cases, according to The New York Times.
At the centre of Trump’s defamation lawsuit is the birthday letter allegedly written by him. According to the Journal, the scrapbook was one of many gifts prepared for Epstein’s 50th birthday. The page allegedly attributed to Trump included a message: “A pal is a wonderful thing. Happy Birthday, and may every day be another wonderful secret,” reportedly typed over a naked female figure, signed with a reportedly stylised “Donald.” As of publication, the Journal has not provided the original document to Trump’s legal team. Trump’s lawyers maintain the drawing and signature are fabrications, arguing he does not produce such documents.
Filed in the Southern District of Florida, Trump’s complaint accuses the Journal of publishing the story with “reckless disregard for the truth” and failing to authenticate the letter. The suit seeks $10 billion in damages. Legal analysts note the high bar for defamation involving public figures, who must prove the material was published with actual malice or reckless disregard for the truth.
The case has also raised concerns about press freedom. Days after the story broke, Journal reporters were reportedly barred from accompanying Trump on a trip to Scotland, what The New York Times described as alleged retaliation. The White House gave no explanation. Journalism organisations warned the move sets a troubling precedent.
