Peter Thiel

In 2007, Gawker Media published that Peter Thiel was gay. Thiel responded by secretly funding Hulk Hogan's invasion-of-privacy lawsuit against Gawker — providing an estimated $10 million or more over approximately three years. The funding was concealed from the public and from Gawker until after the verdict. In March 2016, a Florida jury awarded Hogan $140 million in damages. Gawker declared bankruptcy five months later and sold its assets. In May 2016, Thiel confirmed the scheme to The New York Times, explaining that he viewed it as "one of my greatest philanthropic things that I've done." The explicit goal was destruction of the outlet.

• —Gawker published a post about Thiel being gay in 2007; Thiel later said this was the precipitating event.
• —Thiel secretly retained a litigation finance firm and funded multiple lawsuits against Gawker over several years, with the Hogan case as the primary vehicle.
• —Hulk Hogan (Terry Bollea) was awarded $115M compensatory + $25M punitive = $140M total.
• —Gawker Media filed for bankruptcy in August 2016; its publications were sold to Univision.
• —Thiel to NYT (May 2016): "It's not like I knew about this four years ago and was waiting for the opportunity. For a long time I was angry about Gawker, and one of my friends lost his job because of Gawker."
• —The use of secret third-party litigation funding to target journalism is legal in the United States.
• —No criminal charges were filed against Thiel.

In 1999, before PayPal's IPO, Peter Thiel placed 1.7 million founder shares — valued at $0.001 per share, for a total of $1,700 — into a Roth IRA. At the time, the annual contribution limit was $2,000. Because the shares were entered at their private-market valuation rather than subsequent public-market value, the IRA captured an enormous gain permanently sheltered from taxation. By 2019, the account held $5,004,782,530 — five billion dollars — entirely tax-free, per IRS records obtained by ProPublica. The Roth IRA was designed as a retirement vehicle for ordinary workers; the annual cap in 2024 is $7,000. A middle-class worker maxing their Roth contribution would need over 700,000 years to accumulate $5 billion.

• —ProPublica obtained and published IRS tax records showing the balance as $5,004,782,530.37 in 2019.
• —The mechanism: enter pre-IPO shares at private-company valuation ($0.001/share); after IPO and appreciation, gains are permanently sheltered.
• —The maneuver was legal under US tax code at the time.
• —Congress subsequently moved to restrict so-called "mega Roths" — legislation was included in the Build Back Better Act (passed House, stalled Senate).
• —The 2024 annual Roth IRA contribution limit is $7,000 for workers under 50.
• —ProPublica reported that Thiel's IRA was one of several "mega Roth IRAs" identified in IRS records, but his was the largest.
• —No criminal charges were filed.

Palantir Technologies — co-founded by Thiel in 2003 and on whose board he has served since — built the core surveillance infrastructure used by US Immigration and Customs Enforcement (ICE) for targeted enforcement, case management, and deportation operations. Palantir's FALCON platform (Field Analysis and Continuous Threat Evaluation) integrates data across immigration records, criminal databases, social networks, and financial data to identify and track undocumented immigrants. ICE's Enforcement and Removal Operations (ERO) arm — the unit responsible for arrests and deportations — used Palantir tools during the 2018 family separation policy. Palantir also built predictive policing tools (LION) and intelligence platforms (Gotham) used by CIA, NSA, and local police departments. The company received an estimated $300M+ in US government contracts by the time of its 2020 IPO.

• —Palantir was co-founded in 2003 with CIA venture fund In-Q-Tel as an early investor.
• —The Intercept (March 2017): "Palantir Provides the Engine for Donald Trump's Deportation Machine" — detailed report on ICE contracts and FALCON deployment.
• —ICE ERO contract: $41M (2014); renewed and expanded through subsequent years; ERO is the unit responsible for immigration arrests and deportations.
• —During the 2018 family separation crisis, ICE's operational systems ran on Palantir infrastructure.
• —Palantir engineers internally debated the ethics of the ICE work; one engineer was fired after raising concerns (The Intercept, 2018).
• —Palantir's LION system was deployed for predictive policing in New Orleans without public disclosure; later exposed and discontinued.
• —Thiel remains a Palantir board member. The company went public in 2020; Thiel sold shares but retained board position.
• —No criminal charges have been filed against Thiel or Palantir executives for the surveillance work.

In 2009, Peter Thiel published an essay in Cato Unbound titled "The Education of a Libertarian." The key sentence: "I no longer believe that freedom and democracy are compatible." He identified two groups as the primary threat to the libertarian project: welfare recipients and women voters, whose participation in democracy had made "capitalist democracy" an oxymoron. This was not a private memo. It was a published argument, in his name, in a journal of record for libertarian thought. Nick Land later cited it as a watershed moment in the development of the Dark Enlightenment — the intellectual framework for the tech-right's anti-democratic turn. Thiel then put $15 million into a Super PAC supporting JD Vance's 2022 Ohio Senate campaign. Vance had previously called Trump "America's Hitler" and publicly identified as "never Trump." After Thiel began funding him, Vance reversed course, apologized to Trump, and won the Senate seat. Vance subsequently became Trump's Vice President. Thiel also backed Blake Masters' Arizona Senate race. The pattern is coherent: Thiel published that democracy is an obstacle to the capitalist project, then spent tens of millions to install candidates who would subordinate democratic institutions to that project.

• —Cato Unbound, April 2009: "The Education of a Libertarian" — Thiel writes "I no longer believe that freedom and democracy are compatible."
• —The essay blamed welfare beneficiaries and women voters for making "capitalist democracy" into an oxymoron.
• —Nick Land credited the essay as a foundational text of the "Dark Enlightenment" — the intellectual framework of the tech-right anti-democratic movement.
• —Thiel donated $15M+ to Protect Ohio Values, a Super PAC supporting JD Vance's 2022 Senate race.
• —Vance had previously called Trump "reprehensible," identified as "never Trump," and privately referred to Trump as "America's Hitler" (leaked texts).
• —After Thiel's backing, Vance reversed his Trump position, won the Ohio Senate seat, and became Trump's VP pick.
• —Thiel also backed Blake Masters' Arizona Senate campaign.
• —Co-created 1789 Capital (2022): described as a "parallel economy" combining businesses, media outlets, and political organizations associated with the America First movement.
• —Zero criminal charges.