“Does my bad press give you pause,” Epstein said in the 2015 message.

Thiel responded, “If I had been afraid of bad press, I wouldn’t have gotten anywhere in life… But I hope you’re going well, and this cycle won’t go much further.”

Those emails, and hundreds of others in between, were contained in a cache of Epstein files released by the US Justice Department. While Thiel has said he met Epstein “a few times”, the correspondence reveals the depth and duration of a relationship which, as the emails show, was beneficial to both men.

According to the Epstein files, Epstein, whose emails often contained misspellings and stray punctuation, constantly invited Thiel over and was keen to meet with him as regularly as possible. However, in a November 2017 exchange, he ignored Thiel when discussing who would be the new Treasury Secretary in Trump’s new administration.

In an email to former US Treasury Secretary Larry Summers, he said that Thiel was an “autistic” with “no global understanding”.

Some details of their correspondence have been previously reported by the Stanford Daily, Wired and others. But Bloomberg’s review of the emails offers further insight into how Epstein wooed one of Silicon Valley’s biggest names, a billionaire contrarian who now has deep ties to the Trump administration.

A representative for Thiel declined to comment other than to say that he never visited Epstein’s island in the U.S. Virgin Islands. In a 2024 podcast with Joe Rogan, Thiel said he had met Epstein “a few times” after fellow Silicon Valley investor Reid Hoffman described him as “one of the smartest tax people in the world.” Thiel said he believed Epstein did not go to prison for so long because the crimes were not as serious as charged.

Thiel told Rogan that his willingness to meet with Epstein was a “moral weakness”, adding that he thought Hoffman “always had good judgment about people.” Hoffman recently told Bloomberg that the FBI has cleared him of wrongdoing and welcomed the investigation into Epstein’s connections “to expose those who committed crimes.” He did not respond to a request for comment on this story.

Andrew Mountbatten-Windsor, the former Prince Andrew who was stripped of his royal title last year, has denied the allegations.

Unlike some other prominent figures with whom Epstein courted, Thiel did not discuss sexual matters with him, according to emails reviewed by Bloomberg. In one exception, Thiel suggested that sexual reproduction was a “deceptive strategy” – part of a broader conversation about the role of deception in evolution.

The emails indicate that Epstein and Thiel also communicated over the telephone and the encrypted messaging app Signal, but the details of those communications are not fully known.

Epstein served about 13 months in custody in Florida from 2008 on charges of soliciting and procuring minors for prostitution. In 2019, he was charged with sex trafficking of minors, but was found dead in a New York jail cell before he could stand trial. Authorities concluded that he died by suicide.

The full details of when and where Thiel and Epstein met are not entirely clear. On at least 10 occasions, Thiel was invited to dine with Epstein, either at his Manhattan townhouse or elsewhere, though the emails make it unclear how many times he may have visited. They also discussed Thiel visiting Epstein’s homes in the U.S. Virgin Islands and New Mexico. Thiel did not visit Epstein’s island, his spokesman said. In the email, Thiel said it was very hot in the Caribbean in May.

According to an email from an Epstein assistant, Epstein attended a dinner hosted by Thiel and Hoffman in Palo Alto in 2015 for a group of Silicon Valley dignitaries, and he had lunch at one of Thiel’s offices in California.

Their digital exchanges began in 2014, about five years after Epstein was released from custody in Florida, and continued for more than four years, according to emails reviewed by Bloomberg. The exchange ended in 2019, just months before Epstein was arrested and sent back to prison.

The correspondence ebbed and flowed. They offered to introduce each other to high-profile contacts and discussed everything from cryptocurrencies and magic mushrooms to Brexit and mosquitoes. On the latter point, Thiel said he despises insects.

In an attempt to convince Thiel to meet him in the Caribbean, Epstein indicated that he had sprayed for insects. He wrote, “I spread mist over the island.” He also said he had not seen a mosquito “for years.”

They often did business to increase their wealth. In a 2015 email, Epstein advised Thiel that multimillion-dollar planes were a good way to get tax breaks — and sent an ad for a $12 million jet.

In another example, Thiel advised Epstein on buying shares of private Palantir Technologies Inc. — during a period of internal turmoil at the company — and suggested he should probably wait to get a “better price.”

Epstein wrote to Thiel, who was then Palantir’s co-founder, chairman and majority shareholder, on October 14, 2016, asking, “I am being offered a piece of Palantir at 5.5 views?”

Thiel replied, “$5.50/share? That’s a bit below ‘market’.” He then added, “I suspect you’ll be able to get an even better price sometime in the next 12 months.”

Palantir was then a private company, and BuzzFeed News later reported that it was struggling to retain trophy customers. It is unclear whether Epstein used the information in any trading. Palantir did not respond to a request for comment.

Epstein benefited from another recommendation from Thiel.

In October 2014, Thiel suggested that Epstein put “$10-20MM” into Valar Ventures, a fund focused on early-stage investments that the tech entrepreneur founded. “I will be happy to discuss further when I meet you in person,” Thiel wrote. Epstein will invest $40 million in two funds owned by Valar Ventures, the fund confirmed to The New York Times last year. According to the article, that investment is worth about $170 million today, making it the largest asset still held by Epstein’s estate.

Representatives for Velar did not respond to requests for comment.

According to a July 2018 email, Epstein described himself as “a lead investor with Thiel” in an attempt to convince a cryptocurrency startup to invest anonymously and encouraged him to reach out to Thiel.

A member of the “PayPal Mafia”, an early Facebook investor and co-founder of Palantir, Thiel has built a profile as a Silicon Valley contrarian. He has advocated liberal political views, was an early supporter of Donald Trump, supported the creation of autonomous floating communities in international waters and signed to have his body frozen after he died in the hope that it could be retrieved at some future time.

Recently, Thiel has spoken extensively on the Antichrist. Those with ties to the Trump administration include White House special adviser for AI and crypto David Sachs, Thiel’s colleague at PayPal, and vice president J.D. Vance, who joined Mithril Capital Management, a venture fund backed by Thiel after graduating from Yale Law School.

Epstein earned at least some of his wealth by running a wealth management firm that catered to wealthy clients. In 2008, he pleaded guilty to multiple state charges, including procuring a minor to engage in prostitution.

That same year, Epstein identified Thiel as the person he brought into his inner circle, according to the emails. At the time, Thiel was lecturing on the singularity, a theoretical scenario in which technological advances develop beyond human control. A friend of Epstein’s emailed him to say that he had seen Thiel speak on the singularity at a Google event and “didn’t think he knew what he was talking about.” However, according to the emails, Epstein wanted to meet with her.

The emails indicate that Epstein hoped to meet Thiel in 2011 through a contact with Ian Osborne, a former political consultant who discussed ties to influence in the tech world and brokered meetings between Epstein and other Silicon Valley entrepreneurs, according to the Justice Department cache. Osborne declined to comment. A person close to Osborne said the meeting never took place.

Thiel later said on Rogan’s podcast that he met Epstein in 2014 thanks to Hoffman.

In emails, Epstein regularly listed Thiel under “People to Watch” in his monthly schedule, and his assistant set a reminder to “call Peter Thiel.” DOJ files show that correspondence between the two was sometimes weekly but slowed by the end of 2018. The emails indicate that Epstein used Thiel to his advantage when inviting others into his circle, hanging on to him as a connection he could offer.

He also offered Thiel contacts with politicians and diplomats. This included Bill Burns, who was then Under Secretary of State and later became CIA Director, Anil Ambani, Indian businessman, politician and heir to India’s wealthiest family, and Ehud Barak, former Israeli Prime Minister.

Burns has since said that he “deeply regrets” meeting Epstein. A spokesman for Burns said he had not met Thiel through Epstein and that he “knew nothing about him” before two meetings with Epstein more than a decade ago as he was preparing to leave the government.

It is not clear whether Ambani and Thiel met or not.

A representative for Ambani declined to comment.

Barak apologized for their relationship in an interview with Israeli media earlier this year and said he regretted knowing about Epstein.

Emails indicate that Epstein’s accountant Richard Kahn also took an interest in Thiel.

Kahn requested that Epstein’s personal assistant, Leslie Groff, alert him when Epstein met with Thiel. He would exchange news articles with Epstein over the next few years, regarding Thiel’s allegiance to Trump, his political views, and his bid to buy Gawker, the news and gossip site he helped bankrupt by secretly funding a lawsuit.

In addition to investing in Thiel’s Valar Ventures fund, Epstein sought Thiel’s advice on buying Spotify shares and inquired about whether Facebook, of which Thiel was an early investor and was a board member from 2005 to 2022, had ultimately considered the tax issues for its ill-fated digital currency.

In an extended exchange, Thiel and Epstein discussed the role of “deception” in evolution, the idea being that animal and human predators mimic the appearance or behavior of something else in order to gain an advantage in survival or mating.

Thiel suggested that reintroduction was probably a “deceptive strategy”. Thiel wrote, “Making copies of yourself improves the chances = the predator only gets a copy, not you.”

Epstein responded that deception was “a device to protect or overcome free energy”.

“In short if the predator can read your algorithm, you are easy prey,” he wrote, later adding, “Deceptive confidence is also a winning game strategy.”