After reading The Contrarian, Max Chafkin’s judicious biography of Peter Thiel, the secretive and Trump-supporting tech mogul, I was struck by how much Thiel remains a mystery — less of an intriguing enigma than a hollow cipher. This isn’t to fault Chafkin, who is unfailingly diligent in his efforts to narrate Thiel’s life and understand, as far as possible, what he actually believes. But contrarianism tends to be reactive, not constructive; if there’s truly a there there, it risks getting lost in the incessant repositioning of oneself against a fickle discourse.

... sharp and disturbing ... Chafkin’s chronicle of Thiel’s wild abandon during the Obama years contains some of the most suspenseful passages in the book, as the narrative hurtles toward his acquisition of actual political power ... Chafkin is especially interested in the friction between Zuckerberg and Thiel, who drifted apart for a time as Thiel became more involved in conservative politics. The words spent on discord in this relationship — and on tension between Thiel and other tech titans — distract from the more urgent chronicle of Thiel’s rise as one of the pre-eminent authors of the contemporary far-right movement ... chilling — literally chilling. As I read it, I grew colder and colder, until I found myself curled up under a blanket on a sunny day, icy and anxious. Scared people are scary, and Chafkin’s masterly evocation of his subject’s galactic fear — of liberals, of the U.S. government, of death — turns Thiel himself into a threat. I tried to tell myself that Thiel is just another rapacious solipsist, in it for the money, but I used to tell myself that about another rapacious solipsist, and he became president.

... entertaining and disturbing ... In the end, the answer to the riddle of what Thiel truly believes is a disappointing one—not through any fault of Chafkin’s, but because his subject is less fascinating than he would have us believe. For all his intellectual horsepower, Thiel is a painfully recognizable type to anyone familiar with Tucker Carlson, Stephen Miller or Andrew Breitbart — all brainy conservatives who came of age in California, revolted by, and revolting against, its prevailing progressive mores ... Chafkin’s title has it exactly right: Thiel is a contrarian, a man who doesn’t truly stand for anything — only against. What could be more boring than that?

The title hits the mark. The subtitle causes difficulties ... Despite his limited access to Thiel, Chafkin succeeds in shedding light on his subject’s formative experiences. But then he faces the hard choice: Which of the mature Thiel’s multifarious exploits deserve emphasis? ... At least as of now, showing that Thiel’s political machinations have made a difference is hard. His $1.3 million donation pales next to the tens of millions spent by the hedge-fund billionaire Robert Mercer on the Trumpian right during the 2016 cycle...Seeking nonetheless to build a case for Thiel’s political salience, Chafkin takes a fateful turn. He tortures the evidence to make it scream louder ... Chafkin’s exaggerations are doubly unfortunate. Thiel is indeed a financier of the Republican right, and perhaps he will emerge as a kingmaker with real power in some future political cycle...But drawing dubious connections does nothing to advance this point, and meanwhile Chafkin’s political emphasis obscures another part of his subject. Thiel’s approach to venture capital gets short shrift in his book. Yet venture investing is where Thiel’s contrarianism has yielded the clearest rewards—and where his impact on the world is arguably strongest ... Thiel’s contrarianism may be alarming in its reactionary Stanford Review guise. But an aversion to imitation and a willingness to commit capital to long-shot ideas are also the special forces that drive the most dynamic part of our economy.

Max Chafkin, a Bloomberg Businessweek reporter, relies heavily on biographical details from George Packer’s 2011 New Yorker profile and an expanded version that appeared in The Unwinding. This borrowing was a necessity: whereas Packer enjoyed full access to his subject, Chafkin got only two interviews, off the record, separated by a decade. Thiel might have sensed a hatchet job ... Cheap psychologizing can be the mark of an unsteady biographer. Here it may also indicate an ungenerous one. Chafkin withholds credit and finds fault, starting early and small ... Some connections are stronger. Chafkin adds to prior reporting ... ambiguities make it hard to trust Chafkin as a judge of Thiel’s influence in the worlds he inhabits ... Chafkin seems to be groping toward something more interesting than the notion that Thiel is singularly powerful and maleficent—the idea that Thiel lays bare Silicon Valley’s alarming vision of self-rule, that this story is less one of influence than one of hidden affinity ... Chafkin’s plotting of Thiel’s ideology feels overdetermined, fecklessly connecting recent developments to some distant precursor (he calls Thiel’s support of Trump 'no different from the growth hacking at PayPal'), placing Thiel at the center of broad trends (he claims that Thiel somehow brought the gospel of Ayn Rand to Silicon Valley), and casting every aspect of Thiel’s conservatism as uniformly scandalous ... The Contrarian is most successful in sketching Thiel’s quest, over the past decade, for 'real power, political power.' It’s unfortunate, then, that the more exotic aspects of Thiel’s politics become just another part of the broadside, with insufficient delineation between his libertarianism taxation is theft, except when your company depends on government spending), his common cause with the post-2015 GOP (Trump, nationalism, immigration restrictions), and his truly radical positions, such as his Schmittian distaste for the deliberative premise of liberal democracy.

... it is slightly disappointing to find that in Max Chafkin’s biography The Contrarian, Thiel has been reduced so completely to the role of unlikeable villain. A Bloomberg Businessweek reporter, Chafkin does a good job of chronicling Thiel’s years as intellectual wunderkind, tech investor, would-be hedge fund visionary and rightwing political influencer. Yet sadly, he defaults to a reading that at all times ascribes the worst of motives to its subject who, we are led to believe, set the tech industry on an amoral pursuit of wealth and power. Thiel’s apparent contradictions are certainly plentiful. But then, who said people have to be consistent?

Although childhood passes in a few pages, Chafkin gives the reader inclined to armchair psychoanalysis plenty with which to work ... Chafkin follows the Thiel story through the first year of the pandemic. A lot of this has been previously reported, including by Chafkin himself. But by putting things together, in order, Chafkin makes some important patterns clear ... The Contrarian is primarily plot-driven. But the analogies that it suggests between contrarianism as a media strategy and contrarianism as a business strategy may be crucial to understanding the cultural logic of our time—not to mention the origins of the Silicon Valley culture wars out of which Thiel has emerged as the best-known figurehead ... But replacing heroes with anti-heroes does little to alter the narrative about how a handful of geniuses have changed the world through their insuperable intelligence; the genre continues to trade on a deep desire to make myths about the men behind the machines. And in the case of Thiel, specifically, to focus too much on him as an individual precludes understanding, much less contesting, the nature of his power.

Chafkin accounts for these and other contradictions by casting his subject as a soulless opportunist and an intellectual fraud. Mr. Chafkin doesn’t put it as strongly as that—he prefers insinuation and the passive voice—but at no point in the book does he credit Mr. Thiel with a sincere belief or an honorable motivation. Mr. Chafkin, an editor at Bloomberg Businessweek, wrote the book, he says, to 'understand' Mr. Thiel. But The Contrarian reads as though the author assumed he understood his subject already and set out to take him down a few notches ... Occasionally he provides counterevidence to his own blithe assessments ... Some of Mr. Chafkin’s arrows appear to me to hit their mark...But Mr. Chafkin’s need to portray his subject’s every decision, every utterance as either dishonest, shameful or unethical makes me think, in my own contrarian way, that Mr. Thiel must be a decent guy. It also turns what ought to be a riveting story into a dreary morality play ... Equally tiresome is Mr. Chafkin’s tortured effort to tag Mr. Thiel with regressive opinions on race ... Mr. Chafkin clearly means to suggest Mr. Thiel is a racist, but the author’s reasoning on this score is so circumlocutory that I remain firmly skeptical ... It is a mystery to me why a certain kind of journalist, having decided a public figure is bad in some way, must treat that public figure as irredeemably malign and the source of limitless evil. Whatever the reasons for this convention, it has the effect of turning complicated stories of human frailty and achievement into petty legal briefs. Mr. Chafkin has succeeded in making the story of Peter Thiel the one thing it isn’t—boring.

This account lucidly illustrates Thiel’s rise as a right-wing power broker, during the hi-tech boom, bust, and resurgence; it will appeal to readers fascinated by the intersection of technology and politics.

... [a] revealing portrait ... Chafkin brings long experience in the tech world to his book debut, a savvy biography of billionaire venture capitalist and outspoken neo-reactionary Peter Thiel ... Drawing on interviews with Thiel and more than 150 others, many who insisted on anonymity because they feared Thiel’s retribution, Chafkin deftly portrays his subject as a 'calculating operator,' 'nihilist,' and predator who has constructed an image 'so compelling that it has come to obscure the man behind it' ... A brisk, well-researched life of an enigmatic billionaire.

... cutting ... Chafkin’s portrait of Thiel is punchy and caustic...His zeal to unmask Thiel’s allegedly subversive influence is sometimes overwrought: he calls Facebook CEO Mark Zuckerberg’s 2019 refusal to censor Trump’s campaign claims 'exactly what Thiel, and Trump, wanted,' while downplaying the free-speech issues involved. Still, this is an engrossing look at one of Silicon Valley’s most eccentric and abrasive figures.