Donald Trump

Associates

NYC Real Estate Magnate

Donald Trump and Jeffrey Epstein operated in the same New York–Palm Beach social circuit from the late‑1980s until a very public split in the mid‑2000s.

Photographs, video, flight logs, real‑estate records and court filings confirm regular contact—parties at Mar‑a‑Lago, shared flights, Epstein's presence at Trump's 1993 wedding and a 2003 birthday "gift book."

Their friendship cooled after a bitter 2004 bidding war for a Palm Beach mansion and, according to several contemporaries, Epstein's conduct toward young women at Trump's club, and by 2007 Trump had barred him from Mar‑a‑Lago.

Though no evidence links Trump to Epstein's sex‑trafficking crimes, the association has remained politically radioactive, resurfacing in congressional fights over unreleased "Epstein files," new media leaks and Ghislaine Maxwell's 2025 DOJ interviews.

  Early proximity (1987‑1992)

Both men owned property in Manhattan and Palm Beach and were first photographed together at charity events in the late‑1980s. Time's recent timeline notes that "by 1989 they were already fixtures at the same parties."1

An NBC camera crew filming Trump in November 1992 captured him dancing with Buffalo Bills cheerleaders, then pointing women out to Epstein and whispering in his ear.2 The footage undercuts later claims that they were only casual acquaintances.

  Height of the friendship (1993‑2003)

Newly surfaced CNN‑verified photos place Epstein at Trump's Plaza Hotel wedding to Marla Maples in December 1993.3

Flight logs introduced at Ghislaine Maxwell's 2021 trial show Trump, 11‑year‑old Eric Trump, Epstein and Maxwell flying from Palm Beach to Teterboro on 13 Aug 1995.4 A separate 1997 Palm Beach→Newark hop is listed in pilot David Rodgers's ledger, released by Law & Crime.5

In a 2002 New York Magazine profile, Trump called Epstein "a terrific guy… He likes beautiful women as much as I do, and many of them are on the younger side."6

A Wall Street Journal exposé (2025) revealed a leather‑bound 2003 birthday compilation for Epstein containing an illustrated note purportedly from Trump; Trump now sues the Journal, denying authorship.7

  Business overlap & breaking point (2004)

Both men tried to buy the bankrupt Maison de L'Amitié ocean‑front estate. Vanity Fair and the Washington Post describe an aggressive auction that Trump won with a $41 million bid, souring the relationship.89

  Fallout and ban (2005‑2008)

Page Six (2007) and a Business Insider reconstruction cite Mar‑a‑Lago staff who said Epstein was "banned" after he approached an 18‑year‑old locker‑room attendant for massages.10 Lawyer Brad Edwards later testified he "heard" of the ban but could not confirm it independently.11

When Palm Beach police opened a sex‑offense probe into Epstein in 2005, Trump stopped taking his calls, telling reporters in 2019: "I was not a fan… we haven't spoken in 15 years."12

  Legal and political shadows (2008‑2019)

Epstein's 2008 plea drew no public defense from Trump, who instead began floating that Bill Clinton was the visitor to "Orgy Island."13

A 2016 "Jane Doe" lawsuit accusing both men of 1994 rape was filed, dismissed, re‑filed and dropped again—Politico's docket coverage notes no evidence advanced beyond the complaint.14

When Epstein was rearrested in July 2019, archival NBC video and WaPo interviews with party promoter George Houraney resurfaced, confirming 1992 events and underscoring the depth of the past bond.152

  Re‑emergence of evidence (2020‑2025)

EventDetails
Maxwell trial logs (2021)Added six previously unknown Trump‑Epstein flights, according to Miami Herald reporting.16
Congressional pressure (2024‑25)GOP and Democratic lawmakers now subpoena unreleased DOJ "Epstein files"; Politico details infighting over Attorney General Pam Bondi's limited release and Trump‑allied efforts to constrain it.17
Fresh imagery (July 2025)CNN K‑File and Washington Post each published newly digitized 1990s photos and videos, renewing public interest.318
Tech‑billionaire claims (2025)Elon Musk alleged Trump appears in hidden files—the Post analyzed and found no substantiating documents yet.19
Maxwell's DOJ interviews (July 2025)Washington Post confirms she "answered every single question" about 100 figures; Trump denies considering a pardon.20

  Why the split?

There are several narratives for why they stopped being friends.

FactorEvidenceWeight
Real‑estate rivalry2004 Maison de L'Amitié auction reports from WaPo & Vanity Fair.Strong
Mar‑a‑Lago misconductStaff‑sourced accounts of Epstein recruiting spa workers; Business Insider summary.Moderate
Legal risk managementTrump begins distancing as 2005 police probe surfaces, per WaPo chronology.Moderate
Personal animusTrump's own statement: "The reason doesn't make any difference" (2019).9Weak (non‑specific)

  Evidence log

CategoryConcrete items
Visual media1992 party tape; 1993 wedding photos; multiple Getty images (1987‑2004).23
Travel recordsAt least 7 documented flights (1995‑1997, 2000).45
Contemporary quotesTrump's 2002 "terrific guy" remark; Epstein's 2017 tapes bragging of closeness (Daily Beast PDF).621
Written artifacts2003 birthday "gift book" note attributed to Trump.7
Club logs & banPage Six / BI accounts plus lawyer testimony.1011

  Conclusion

Documentary evidence places Trump and Epstein in a friendly, mutually useful relationship from the late‑1980s until 2004‑07, anchored by shared social circles, real‑estate interests and a taste for lavish parties.

The friendship ended amid a property bidding war and rising fears around Epstein's behavior at Trump's club. Since 2019, every fresh leak—flight logs, photos, birthday notes—has reignited political pressure, but to date no released record ties Donald Trump to Epstein's sex‑trafficking crimes.

  • DOJ "Epstein files" and Maxwell's debriefing remain sealed
  • Trump's WSJ libel suit over the birthday note may require forensic review

  References

  Footnotes

  1. Trump Epstein Relationship Timeline, Time Magazine

  2. Trump Epstein Mar-a-Lago Party, Washington Post 2 3

  3. CNN Epstein Trump Transcript, CNN 2 3

  4. Trump Epstein Flight With Son, Business Insider 2

  5. Epstein Flight Logs Maxwell Trial, Law & Crime 2

  6. Epstein International Moneyman Mystery, New York Magazine 2

  7. Epstein Birthday Book Trump, New York Magazine 2

  8. Trump Epstein Real Estate Rift, Vanity Fair

  9. Trump Epstein Palm Beach Mansion, Washington Post 2

  10. Trump Epstein Palm Beach Fallout, Business Insider 2

  11. Trump Epstein Connection Addressed, Business Insider Africa 2

  12. Trump Epstein Terrific Guy Quote, Washington Post

  13. Epstein Conspiracy Theories Politics, Washington Post

  14. Trump Teen Rape Suit Dropped, Politico

  15. Trump Epstein Party Video Story, Washington Post

  16. Maxwell Logs Trump Epstein Flights, Miami Herald

  17. House GOP Epstein Files Warning, Politico

  18. Epstein Controversy Timeline Trump, Washington Post

  19. Musk Trump Secret Epstein Files, Washington Post

  20. Maxwell DOJ Trump Interview, Washington Post

  21. Epstein Tapes Trump Closest, U.S. House of Representatives

Published on July 26, 1987

6 min read