For years, former President Donald Trump has insisted that he was “no fan” of Jeffrey Epstein, the convicted sex offender whose name has been linked to some of the world’s most powerful men. But a fresh, in-depth review by CNN’s KFile team has reignited public interest in their relationship, pulling together photos, videos, flight records, and court documents to paint a more detailed picture of how close the two men once were.

A Comprehensive Timeline of Their Connection

The CNN review, led by senior editor Andrew Kaczynski, traced Trump and Epstein’s interactions across nearly two decades. The pair were repeatedly photographed at Mar-a-Lago parties, weddings, fashion shows, and New York society events in the 1990s and early 2000s.

The report didn’t rely on speculation. Instead, the journalists sifted through hundreds of hours of footage, lawsuit exhibits, and legal filings to establish a timeline of contact between the two.

What the Flight Logs Show

One of the most talked-about findings involved Epstein’s flight records, which have been central to many court cases. Trump’s name does appear in these logs, documenting that he flew on Epstein’s private jet in the 1990s. While the number of flights attributed to Trump remains debated, CNN highlighted that these records prove he was not as distant from Epstein as he has claimed in recent years.

Associates Remember Them Differently

Adding weight to the timeline, interviews with Epstein’s acquaintances suggest that their relationship was once friendly and familiar. CNN reported that multiple people within Epstein’s circle described Trump as a regular social contact—contradicting Trump’s later insistence that he barely knew him.

Why This Matters Now

The renewed spotlight on Trump’s Epstein ties comes as the former president continues to dominate headlines ahead of the 2026 midterm election cycle. For critics, the investigation underscores a long-standing pattern of Trump downplaying or distancing himself from figures who later became liabilities. For supporters, it raises the question of how much responsibility a political figure should bear for associations from decades past.

The Bigger Picture

CNN’s KFile investigation doesn’t claim Trump engaged in Epstein’s crimes, but it does highlight a pattern of proximity, access, and social overlap that contradicts Trump’s public denials. At a minimum, the evidence adds nuance to the narrative and raises important questions about accountability, transparency, and the company kept by public figures.

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