United States prosecutors and federal law enforcement spent over a year examining ties between Jeffrey Epstein and Customs and Border Protection officers stationed in the US Virgin Islands (USVI), according to documents recently released by the Department of Justice.

As The Guardian and New York Times have reported, emails, text messages, and investigative records show that Epstein cultivated friendships with several officers, entertaining them on his island and offering to take them for whale-watching trips in his helicopter. He even brought one cannolis for Christmas Eve. In turn, Epstein would bring certain officers his complaints about his treatment at the hands of other CBP and federal agents. Most of the interactions described in the records occurred years after Epstein pleaded guilty to charges of sex crimes in Florida in 2008.

The CBP officers were never charged for any crimes related to Epstein, and at least one later retired from the agency with a pension, suggesting that the government ultimately didn’t find any wrongdoing. The documents do, though, describe patterns of behavior—two of the officers referred to Epstein as a “friend”—that one government ethics expert described as inappropriate and possible violations of federal guidance. They also contain grand jury subpoenas that specifically name the officers and compel the recipients, which were largely financial services firms, to aid federal prosecutors who were looking into allegations of a conspiracy to defraud the US government.

CBP and the Southern District of New York US Attorney’s Office, which led the investigation into Epstein, did not respond to requests for comment.

For years, Epstein allegedly brought countless women and girls as young as 12 to his private island, Little Saint James, according to a 2020 complaint filed by the former USVI attorney general. Epstein would often fly in and out of USVI on his private jet.

In order to depart from USVI to other parts of the US, Epstein’s plane had to be cleared by CBP, according to a November 2020 FBI interview report with Epstein’s personal pilot, Larry Visoski.

Visoski told the FBI that some passengers were college students with letters from their schools explaining why they were traveling. Other times, according to the report on Visoski’s interview, Epstein traveled with a woman who had a foreign passport. If CBP officers started questioning these passengers, Visoski said, Epstein would intervene and start arguing with the officers.

Visoski, though, told the FBI that Epstein made an effort to be friendly with CBP officers, at times instructing Visoski to collect agents’ contact information. (In an email to one CBP officer, Epstein wrote, “as you know Im very respectful of people just doing their job.”) Over the years, emails and text messages show, various CBP officers would try to reach out to Epstein, either directly or through Visoski or other associates. Sometimes, Epstein would have the officers out to Little Saint James.

In May 2014, for example, Visoski emailed Epstein, “While going through customs in STT, our nice person gave me his cell contact.” The pilot added that the “nice person” would be available to visit Little Saint James that week. Visoski also attached the person’s contact information. The next day, Epstein’s island estate manager emailed Epstein to let him know the person, a CBP officer, would be picked up on Wednesday for lunch. (It’s unclear whether this lunch ever happened.)

Emails in 2015 and 2016 show that Epstein would have another officer, Glen Samuel, come to Little Saint James to perform steel pan drums—a side gig Samuel informally advertised at one point on his Facebook page. In a January 2015 email thread, Epstein asked an associate to clarify Samuel’s rate. The associate replied, “Mr. Samuel says he does not intend to charge you. He considers you a friend and was doing this for you. If you wish to give him something, he is appreciative, but there is no fee.” Samuel did not respond to a request for comment.