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.”

Glover confirmed to WIRED that she was looking to coordinate with Epstein on persuading Saudi Arabia’s Public Investment Fund to commit to financing the take-private deal, an arrangement Musk had previously discussed with the fund’s representatives. PIF did not immediately respond to a request for comment on whether any of its representatives were ever in contact with Glover or Epstein about the deal.

“At the time, Tesla’s leadership was pushing hard for ways to help complete the public-to-private transaction Musk had announced,” Glover says. “The Saudis, and [Saudi Crown Prince Mohammed bin Salman], were key to that. I’d heard that Epstein was close to MBS, so I reached out.”

Glover said that Musk was “never aware” of her communications with Epstein. There is no evidence that Musk directed Glover to contact Epstein in the matter.

Glover talked up Tesla to Epstein in subsequent correspondence, noting its gross profit margin and the potential of its energy business, which she claimed was “projected to be larger than the automotive business.” She also alluded mysteriously to the promise of Autopilot, Tesla’s driver-assistance system, calling it “the elephant in the room all see but don’t comprehend.”

Epstein expressed certain doubts, citing the importance of “cash flows” and “STABILITY. in all its forms.” Glover responded in part by defending Musk’s performance as an executive. “Interesting fact about leader is that those around him accomplish the impossible because they witness his ethics and drive—yes sometimes also too transparent and without artifice, but that is always as a reaction to a perceived injustice or malfeasance,” she wrote. Epstein countered that “bottom line is at the core,” though he also assured Glover, “I only say great things about your boy.”

It was clear, however, that Musk’s troubles around that period made Epstein wonder if a deal was possible. In an email where he laid out reasons why Saudi money was far from a sure thing, he wrote that with Musk there was “concern over the recent strings of outbursts. earnings call etc. Thailand. emotional performance.” The mention of “Thailand” was presumably a reference to Musk’s “pedo guy” tweet and the resulting fallout.

Glover still believed Epstein could help rescue a possible deal that Musk had announced without proper assurances. “I shared publicly available information about the company, with the intent that Epstein would advise the Saudis to hold steady on their commitment to Musk to take the company private,” she tells WIRED. “I was trying to encourage him to weigh in with the Saudis to keep their word to Musk.”

In an August 13 message to Epstein, Glover estimated that they’d need a maximum of $10 billion in cash for the deal, saying that this was “solely my own opinion.” A few hours later, Epstein relayed this figure to financial reporter Landon Thomas Jr., then at The New York Times, framing it as a number that came straight from Musk: “elon said they need less than 10b in cash,” he wrote.

In addition to speculating about deal terms, Epstein and Glover compiled a list of names in an email thread with the subject line “Other Names.” Glover confirms to WIRED that these “were Epstein’s recommendations for potential board members” at Tesla.

In an August 16 message, Glover suggested “Former Dep AG and Pepsico GC Larry Thompson? Richard Parsons? Janet Napolitano? Indra will have more time after 10/3? Jill Abramson?” Epstein replied with a list of his own: “jill . best of list. so far. . larry summers? kathy ruemmler. margaret thatcher ? someone like a sen mitchell or bill richardson. . samantha powers?”

Margaret Thatcher, the former prime minister of the United Kingdom, had died five years earlier. None of the other recommended candidates appear to have served on Tesla’s board. After beginning to work up the list with Epstein, Glover emailed him, “Thx. Msg sent.” Asked if this meant she had forwarded any of the names to Musk, Glover was unsure. “I can’t recall what this was referencing,” she says. “It was a long time ago.”

Epstein and Glover simultaneously strategized on how Musk might navigate tricky media coverage of his travails: “as im sure you are aware some of the papers are looking into whether you boy was on drugs,” Epstein wrote to Glover in mid-August of a forthcoming Times piece. “Nothing to it,” Glover replied. “He barely even drinks.” She later predicted that “what they’ll figure out is that he is pathologically transparent and way too honest.” The pair at one point arranged to speak by phone about the coverage.

Epstein told Glover in an email that he was “Happy to help shape your story,” offering to do so with “No fingerprints.” He drew the line, though, at a “deep background” conversation with James B. Stewart, one of the four Times reporters to share a byline on the story, telling Glover: “no thanks. I live in dark background.” The article, published August 16, was centered around an hourlong interview with Musk, who discussed his emotional fragility and feelings of burnout. It also addressed concerns among Tesla board members about his use of the sedative Ambien.

It seems that Epstein saw the profile as a win. In an August 20 exchange where he asked Thomas if the “tesla thing” was “put to bed,” the reporter answered: “I think his talking released some of the immediate term pressure on him — even if [it’s] for a short while. It was a smart move.” Epstein wrote back, “agreed.” In the course of that exchange, Thomas indicated that Epstein had played an important role in setting up the Musk interview, telling the financier that “the Elon get was epic,” adding, “You delivered!”

Epstein also commended Stewart on the piece. “Good work- interview, jeffrey,” he texted the reporter on August 17.

The article contained no mention of or comment from Epstein. But despite his email to Glover about refusing to comment for the piece, Wall Street Journal business reporter Tim Higgins wrote in Power Play, his 2021 book about Tesla, that Epstein did sit for a background interview with Stewart, who had heard rumors that Epstein was aiding a search for a new Tesla chairman at Musk’s direction.

When the Times asked Musk about this, he hit the roof, Higgins reported: “Epstein, one of the worst people on Earth, actually told NYT that he was working with Tesla and me on the take-private,” Power Play quotes Musk as venting to Glover, “and, under that guise, confided in them ‘concerns’ that he had about me. That was incredibly creepy and diabolical.” When Musk got on the phone to deny Epstein’s claims, according to Higgins, the call turned into the lengthy interview that gave the Times the meat of their article.

The press did relatively little to repair Musk’s reputation, and Tesla shares tumbled. It would also do nothing to salvage a theoretical Saudi-backed bid to buy Tesla. On September 27, when the SEC sued Musk over his August tweet, Epstein emailed Glover, “rough road ahead sorry.”

Stewart texted Epstein the same day to relay the news of the SEC complaint. “Yup,” Epstein responded, “most people believe the middle easterners. bluster. Bloviating bragging. its their language. elon just wasnt fluent in it.”