For Elon Musk, the US Justice Department’s release of 3 million additional files related to criminal investigations of Jeffrey Epstein last month was immediately embarrassing. Attention in particular fell on emails Musk sent the financier several years after he pleaded guilty to solicitation of prostitution and of procurement of minors to engage in prostitution in Florida and registered as a sex offender.

“What day/night will be the wildest party on your island?” Musk wrote in November 2012, for example, appearing to seek an invite to Little Saint James, Epstein’s private island in the Caribbean.

While there has been no confirmation that any such visit occurred, the messages contradict Musk’s long-standing insistence that he didn’t know Epstein well and had always rebuffed his overtures. Other files reveal that an associate of Musk’s spent weeks corresponding with Epstein behind the scenes of a major drama for Tesla and its embattled chief executive.

Musk did not return a request for comment.

A batch of emails reviewed by WIRED shows that in 2018, after Musk posted on social media that he was “considering taking Tesla private” in a move that never came to fruition, one of the CEO’s surrogates was sounding out Epstein for advice on financing the deal and potential board members for a reorganized Tesla. They also went back and forth over Musk’s leadership qualities.

Musk was having a difficult time in 2018, beset by challenges at his companies while his increasingly erratic behavior on social media seemed to take its toll on his public image. That June, as the world waited in suspense for the rescue of a Thai youth soccer team trapped in a submerged cave, he’d decided to involve himself. What he offered was a miniature submersible that he claimed could transport the children through narrow underwater tunnels to safety. The idea was rejected as impractical, with one cave diver dismissing it as a publicity stunt. Musk lashed out at this man on Twitter, calling him a “pedo guy.” He later deleted the post and apologized, but doubled down on the insult in emails to BuzzFeed News, which published them.

The incident led to that individual filing a lawsuit against Musk, alleging defamation, and Musk eventually won the court case a year later. But amid the unfolding PR disaster, Musk took counsel from the high-powered lobbyist and consultant Juleanna Glover as he sought to limit blowback. It was Glover who would later backchannel with Epstein about a plan to take Tesla private.

The idea of buying Tesla was sketchily outlined in another now-infamous Musk tweet. “Am considering taking Tesla private at $420,” he posted on August 7, 2018, adding: “Funding secured.” In fact, he had not secured those funds, and on September 27, the US Securities and Exchange Commission filed fraud charges against Musk, alleging “securities fraud for a series of false and misleading tweets.” Musk quickly settled to the tune of a $20 million fine, with Tesla paying an equal penalty, and stepped down as chairman of the electric vehicle company. (Musk neither admitted nor denied the truth of the SEC’s allegations.)

In the weeks between Musk’s reckless tweet and the SEC charge, Glover was working behind the scenes to make the deal a reality—and sought Epstein’s counsel, emails published by the DOJ show.

“If you are advising re: sovereign funds looking to help a prominent company go private, let me know if I can help w any approp additional information,” Glover wrote to Epstein on August 12. Epstein responded: “Clever.”