In the twisted world of Jeffrey Epstein’s elite circle, newly unsealed files expose a chilling scheme: the convicted predator boasted of handpicking a fiery, glamorous woman—later linked to Donald Trump in rumored romance whispers—as part of his calculated playbook to bond with powerful men through shared “trophies.

Revelations from Jeffrey Epstein’s 2003 50th birthday book, released by House Democrats in September 2025, have reignited scrutiny of his close ties to Donald Trump. A particularly disturbing page features a novelty check and caption joking that Epstein “sold” a “fully depreciated” woman to Trump for $22,500, highlighting their shared world of money, power, and women.

The entry, contributed by Mar-a-Lago member Joel Pashcow, shows Epstein holding a giant fake check signed “DJ Trump.” The woman’s face is redacted, identified as a European socialite in her 20s whom both men pursued. Sources describe intense rivalry: Epstein dated Norwegian heiress Celina Midelfart, a fiery blonde businesswoman, while competing with Trump. Flight logs confirm she flew on Epstein’s jet multiple times in the 1990s.

Trump, then dating Midelfart, reportedly “won” her temporarily before moving on to Melania Knauss. Epstein allegedly boasted of “giving” Trump his ex-girlfriend, per leaked emails and accounts. The “depreciated” joke implies a transactional view of women, echoing Epstein’s trafficking patterns.

This calculated pairing raises unsettling questions: Was it mere playboy banter, or part of Epstein’s strategy to entangle influential men for leverage or kompromat? Trump and Epstein socialized extensively in the 1990s–early 2000s, partying at Mar-a-Lago and New York events with young models.

Trump once called Epstein a “terrific guy” who liked “beautiful women… on the younger side.” Their fallout around 2004–2005 followed a property dispute, but the birthday book—compiled by Ghislaine Maxwell—captures their bond at its peak.

No evidence implicates Trump in Epstein’s crimes, and he denies wrongdoing. Yet the “sale” jest, amid December 2025 file releases showing their photos together, fuels speculation about intent. Critics argue it reveals a predatory culture; defenders dismiss it as crude humor among elites.

As Epstein’s network unravels, such artifacts expose how power blurred lines between friendship, rivalry, and exploitation. The fiery Midelfart rivalry underscores Epstein’s manipulative matchmaking—perhaps harmless to some, but profoundly disturbing in hindsight.