The release of new documents related to Jeffrey Epstein has revealed more details about the friendship he shared with Naomi Campbell. The two first met in 2001, marking the beginning of a friendship that lasted until 2016, when Campbell’s request to use one of Epstein’s private jets was initially denied, reportedly ending their relationship.

Campbell continued to associate with Epstein even after he was convicted of soliciting a child for prostitution and served time in prison. She invited him to multiple events, and the newly released records show that the two remained in regular contact via phone and email.

Among the events Campbell invited Epstein to was her 2004 birthday party in St. Tropez him to two events in Paris and Moscow.

The party in Paris celebrated Campbell’s 25-year association with Dolce & Gabbana. In Moscow, she invited Epstein, and Campbell co-hosted a NEON event alongside Dasha Zhukova, the wife of Russian billionaire Roman Abramovich.

While Epstein’s criminal conviction did not immediately end their friendship, Campbell’s unsuccessful request to use one of his private jets to travel to Miami reportedly caused a rift. According to recently released documents from the U.S. Department of Justice, an unnamed person emailed Epstein regarding Campbell’s request.

The emails do not provide a clear timeline of events preceding Campbell’s request, nor do they indicate whether Epstein had previously promised to lend his jet. Regardless, Epstein had reportedly left the city by the time the request arrived. He allegedly instructed the redacted contact to inform Campbell that he had to depart due to “weather.”

A few days later, the redacted individual emailed Jeffrey Epstein, writing, “Naomi has called back twice now saying she doesn’t have any backup plan as she really thought from you. This would work so she has booked the hotel and car and driver…” The message added, “She’s wondering if the plane can’t take you to where you are going, then go back and get her to take her to where she needs to be. She’s certainly spreading on this and hopes you will call her.”

Epstein reportedly asked his pilot, Larry Visoski, to find Campbell a charter. On Jan. 26, when the unnamed person reached out to the supermodel to arrange a meeting with Epstein, she did not respond. The next day, Jan. 27, the redacted individual wrote to Epstein: “FYI, I have called, texted and emailed Naomi that you will be in town today and tomorrow, but I have not been able to speak with her and she has not replied to anything.”

Naomi Campbell had previously traveled on Epstein’s infamous Lolita Express, as revealed in 2010. According to the documents, it was the fiasco over arranging the charter that ultimately ended the nearly 15-year friendship between Campbell and Epstein.