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Were there any business dealings between Donald Trump and Jeffrey Epstein?
Executive summary
Available reporting documents social and occasional business overlap between Donald Trump and Jeffrey Epstein in the 1990s and early 2000s, including visits to each other’s properties and at least one contested commercial episode tied to a beauty-pageant event at a Trump venue [1]. Trump has publicly said he broke off ties before Epstein’s 2008 plea [2], while recent political moves by Trump and his administration have focused DOJ attention on Epstein’s ties to others and have renewed scrutiny of past connections [3] [4].
1. A social-professional relationship, not hidden from contemporaries
Reporting and compilations show Trump and Epstein had a social and professional relationship beginning in the late 1980s and extending into the early 2000s, characterized by mutual visits to real-estate properties and appearances at the same social events [1] [5]. Journalists describe their interaction as “friends” during the 1990s and 2000s, which framed later political and legal scrutiny when Epstein’s crimes became widely known [2].
2. Documented business friction tied to a beauty-contest event
One concrete commercial episode often cited involves a 1993 “American Dream Calendar Girls” event at Trump Castle in Atlantic City. The venue’s operator later said it lost money; the promoter sued Trump in 1995 claiming he had been cheated out of a $250,000 fee and larger future earnings — a dispute presented in coverage as a business clash rather than evidence of long-term joint enterprises [1]. Rolling Stone and other timelines place this dispute amid the broader arc of social and transactional ties between the men [5].
3. No source here claims an ongoing formal business partnership
The set of documents and articles you provided describe social ties, property visits, shared events, and contest-related litigation — but they do not assert a long-term, formal joint business partnership between Trump and Epstein. Available sources do not mention a corporate joint venture or sustained co-ownership arrangement beyond social dealings and episodic commercial friction [1] [5].
4. Trump’s public position: “broke off ties” before criminal conviction
Trump has said he cut off his relationship with Epstein before Epstein’s 2008 guilty plea; contemporary outlets record Trump’s statement that he broke off ties and stress his contention that the association ended years earlier [2]. Reporting also notes Trump’s efforts, years later as president, to direct scrutiny toward Epstein’s connections with other prominent figures — a move interpreted by some critics as political deflection [3] [6].
5. New political context has reopened scrutiny and released documents
In late 2025, the release of tens of thousands of emails from the Epstein estate and subsequent political action — including Trump directing Attorney General Pam Bondi to investigate Epstein’s ties to several Democrats and business figures — has reignited interest in all associations recorded in the archive [7] [3]. The Justice Department’s assignment of a top prosecutor following Trump’s urging is documented in multiple outlets [4] [3].
6. Competing interpretations and possible motives in recent investigations
Some Republicans and Democrats pushing to make Epstein-related files public argue transparency is necessary; other Republicans (including some quoted critics) say Trump’s ordering of investigations could be a “smokescreen” to delay or block full file releases because active probes can legally withhold documents [7] [6]. Coverage emphasizes that political incentives — to deflect attention, to demand transparency, or to protect reputations — shape how these revelations and probes are portrayed [6] [8].
7. What these sources do not say or prove
The materials provided do not present evidence that Trump participated in Epstein’s criminal activities, nor do these sources assert a long-running business partnership beyond episodic property visits and social interactions; they also do not provide exhaustive transactional records between the two men. Available sources do not mention detailed contractual business ventures or joint companies backed by both men [1] [5].
8. Bottom line for readers
If your question is whether there were contacts and at least one dispute involving a business event at a Trump venue — yes, reporting documents social ties and a contested commercial episode [1]. If your question is whether the sources supplied here prove a formal, sustained business partnership or criminal collaboration between Trump and Epstein, the sources do not make that claim and do not contain the transactional proof needed to conclude so [1] [5].