When It Comes to Jeffrey Epstein, There Are a Lot of Strange Disney Connections

In accordance with the Epstein Files Transparency Act, which was signed into law on Nov. 19, 2025, the so-called Epstein files had to be released one month later. That kind of happened. The Department of Justice began a slow rollout on Dec. 19, starting with heavily redacted photos. To no one's surprise, Bill Clinton was featured the most.

Images of Clinton were released without any context. In one, he is sitting in a jacuzzi with his head tilted back. In another, the former president is swimming in a pool with Epstein co-conspirator Ghislaine Maxwell. President Donald Trump was not pictured in this latest batch. One of the more surprising characters to appear in the Epstein files is Winnie the Pooh. Say it ain't so! Here's what we know about the beloved bear's shocking inclusion in the files.

Seeing Winnie the Pooh leave the Hundred Acre Wood to spend time with Epstein was shocking, but easily explained. In the photo, the financier and an unidentified man are seated at a table. Behind them, someone dressed as Winnie the Pooh has their arms around the shoulders of Epstein and his companion. It's not known who took the photo.

Because Epstein lived in Florida, it's safe to assume this picture may have been taken in a dining establishment at Disney World. To figure this out, we turned to the kind of person who would undoubtedly know where this occurred: a Disney adult. Per the DisneyFanatic website, this photo, along with one of Epstein with Piglet, was snapped in The Crystal Palace on Main Street, at the Magic Kingdom. This whimsical restaurant is where all the animals of the Hundred Acre Wood come out for photos and friendship.

In February 2023, The New York Times reported on some questionable emails between Epstein and James E. Staley, who was the lead private banker of JPMorgan Chase. Staley was the man who made sure Epstein was a loyal client for 15 years. The emails were made public in a lawsuit filed by the attorney general of the U.S. Virgin Islands, where Epstein's island was. It accused JPMorgan Chase of having knowledge of Epstein's activities on the island.

"JPMorgan had a more than close-up view of Epstein’s sex-trafficking," said the lawsuit. They found that Epstein emailed Staley "photos of young women in seductive poses," and that the two had engaged in "discussions of sex with young women." After one visit to the island, Staley emailed Epstein to say he had fun. "Say hi to Snow White," he wrote. Prosecutors believed Epstein used Disney princess names as codes for young girls.

According to the Associated Press, because Epstein lived in Florida, numerous posts on social media have attempted to connect him to Disney. One claim stated that snorkeling trips that a Disney-affiliated tour provider ran were near Epstein Island. Disney later confirmed in an emailed statement that there were no tour stops on that island.