Book excerpt examines Peter Thiel's support for Trump and partnership with Steve Bannon, libertarian ideology, battles with the IRS, and founding of Palantir
In an exclusive excerpt from The Contrarian, a new biography, the disruption-preaching power broker is revealed … Tweets: @s_m_i , @chafkin , @jimaley , @chafkin , @bw , @chafkin , and @silviakillings Tweets: Stacy-Marie Ishmael / @s_m_i : [The tech CEOS] implied it would be fine to crack down on illegal immigrants as long as Trump would be able to supply their companies with enough skilled foreign workers. “We should separate the border security from the talented people,” [Tim] Cook said. https://www.bloomberg.com/... Max Chafkin / @chafkin : We were promised flying cars https://www.bloomberg.com/... https://twitter.com/... Jim Aley / @jimaley : “Peter's idea of disrupting government is *out there*,” Steve Bannon says. “People thought Trump was a disrupter. They had no earthly idea.” https://www.bloomberg.com/... Max Chafkin / @chafkin : this week's @bw cover is an excerpt from my new book. It asks: What did Peter Thiel get out of his 2016 endorsement of Donald Trump? Answer: A lot! https://www.bloomberg.com/... @bw : NEW COVER: This is the inside story of how Peter Thiel gamed Trump, Silicon Valley's biggest executives, and democracy itself to make billions, tax-free https://www.bloomberg.com/... https://twitter.com/... Max Chafkin / @chafkin : conventional wisdom said Thiel would be a moderating force on the White House. Turns out he was too extreme for Trump https://www.bloomberg.com/... https://twitter.com/... Silvia Killingsworth / @silviakillings : Trump's presidency was great for Peter Thiel, writes @chafkin, who's got a Blockbuster @BW cover and a book out next week https://www.bloomberg.com/... https://twitter.com/...
Context & Ripple Effects
Max Chafkin's The Contrarian arrives mid-arc in Thiel's public transformation from contrarian VC to open political operative. The defense he offered after his 2016 Trump donation and his 2017 attempt to explain himself to Silicon Valley read now like early installments of the story this book consolidates: the Bannon partnership, the IRS battles, and the alleged use of political influence to shelter billions.
The stakes are not only biographical. At Palantir, CEO Alex Karp has spent years arguing his progressivism offsets the Thiel-Trump association, while the company's own trustworthiness remains contested — so every revelation about how Thiel built his fortune lands on a company still selling its services to governments.
First-order effects
- The book converts long-whispered claims into a documented narrative: Thiel's legal battles with the IRS and the alleged tax-free billions become part of the public record he must answer to, alongside the disclosed Bannon partnership.
- Palantir inherits fresh reputational exposure — Karp's progressive counter-framing, already deployed against the Trump association, now has to cover tax and ideology allegations aimed at the co-founder himself.
Second-order effects
- The reputational cost of proximity to Thiel sharpens for other tech figures: he already struggled to recruit the tech elite to Trump's team in 2016 (turning to Max Levchin for advice with a shortlist including Blake Masters), and the book gives executives a concrete reason to keep their distance.
- Meta's board comes under renewed pressure to justify hosting a director openly bankrolling far-right candidates — pressure that culminates in his eventual departure to focus on politics.
Third-order effects
- If the pattern holds, the structural shift is founder-as-powerbroker: venture-scale wealth converted directly into campaign infrastructure, party influence, and candidate pipelines rather than philanthropy or policy patronage.
- The IRS allegations point toward a longer reckoning with how founder fortunes are structured — if tax engineering becomes a political liability, expect regulatory attention to follow the publicity, though whether it does is genuinely uncertain.
The trend: Silicon Valley fortunes are being converted directly into partisan political power, with Thiel as the template — company-building, tax strategy, and campaign funding run as one portfolio.