National Post (Latest Edition) - - FRONT PAGE - Alyssa Rosen­berg

In this age when peo­ple com­pete to be con­trar­ian, it’s rare to en­counter a gen­uinely star­tling propo­si­tion. That’s what makes the premise of Ryan Hol­i­day’s Con­spir­acy such a de­light. It takes real chutz­pah, dur­ing an in­ves­ti­ga­tion into pos­si­ble col­lu­sion to swing the 2016 pres­i­den­tial elec­tion, to ar­gue that we might be bet­ter off “if more peo­ple took up plot­ting.”

Un­for­tu­nately for Hol­i­day, and for read­ers who en­joy a good provo­ca­tion, his book fo­cuses on a case that demon­strates why trans­parency beats con­spir­acy in the long run.

Con­spir­acy chron­i­cles the le­gal bat­tle be­tween Terry Bol­lea, bet­ter known as pro­fes­sional wrestler Hulk Ho­gan, and Gawker Me­dia, the swash­buck­ling Man­hat­tan pub­lish­ing group founded by Nick Den­ton.

In 2012, A. J. Daule­rio, then ed­i­tor of the com­pany’s flag­ship site, pub­lished ex­cerpts of a sex tape, recorded in 2006 with­out Bol­lea’s con­sent or knowl­edge, that showed Bol­lea in bed with Heather Clem, who was then mar­ried to Bol­lea’s best friend: the ra­dio per­son­al­ity Bubba the Love Sponge.

The story may seem wacky al­ready, but this is when it gets truly weird.

In 2007, Gawker Me­dia ac­quired a pow­er­ful and pa­tient en­emy when one of its writ­ers outed PayPal founder and ven­ture cap­i­tal­ist Peter Thiel as gay. Gawker’s Den­ton, who like Thiel is gay and lib­er­tar­ian, be­lieved that Thiel’s re­fusal to be open about his gay­ness was proof that Thiel was “para­noid.” To Thiel, the story was a ter­ri­ble vi­o­la­tion, one that made him into an ob­ject of cu­rios­ity, in a way he found in­com­pre­hen­si­ble.

Thiel, as Hol­i­day writes, “ven­er­ated pri­vacy, in cre­at­ing space for weirdos and the po­lit­i­cally in­cor­rect to do what they do.

Be­cause he be­lieved that’s where progress came from.” What Gawker saw as trans­parency, Thiel saw as a threat to Sil­i­con Val­ley. He was so an­gry at Gawker that he be­gan to re­fer to it as ” the Man­hat­tan Based Ter­ror­ist Or­ga­ni­za­tion."

But it took him four years to strike back. In 2011, a Mr. A, whose role is first de­scribed in Con­spir­acy but who re­mains a shad­owy fig­ure through­out the book, per­suaded Thiel to de­vote $ 10 mil­lion and five years to a shell com­pany aimed at find­ing and back­ing po­ten­tial law­suits against Gawker. Among their ben­e­fi­cia­ries: Terry Bol­lea. In 2016, a Florida jury awarded Bol­lea dam­ages so pun­ish­ing that Den­ton had to sell the com­pany. On the sur­face, it seemed that Thiel’s con­spir­acy had check­mated Gawker Me­dia.

Hol­i­day, an au­thor and cor­po­rate ad­viser, had un­usual ac­cess to Thiel and Den­ton. It is one of the many ironies of this story, and of Con­spir­acy, that talk­ing makes Thiel more sym­pa­thetic and com­pre­hen­si­ble than plot­ting ever did. But by the end of the book, it’s clear that, de­spite Hol­i­day’s ar­gu­ment, Thiel’s con­spir­acy failed: Thiel killed Gawker, but in do­ing so un­der­mined his dream of mak­ing the In­ter­net a more de­cent place and se­cur­ing a more pri­vate life for him­self. By con­trast, Gawker was de­stroyed not be­cause its lead­ers failed to con­spire, but be­cause they didn’t pur­sue the trans­parency they claimed to believe in.

One of the chal­lenges con­spir­a­cies face is that they tend to mis­take their most dif­fi­cult tasks, such as killing Abra­ham Lin­coln or Gawker, for their larger goals (win­ning the Civil War or clean­ing up the In­ter­net). Yes, John Wilkes Booth man­aged to as­sas­si­nate the president. And yes, by the end of Bol­lea v. Gawker, Gawker was dead. But Hol­i­day strangely fails to ac­knowl­edge that Lin­coln’s death didn’t pre­vent the Con­fed­er­acy’s de­feat in the Civil War or the Re­con­struc­tion that fol­lowed, and Booth didn’t live long past the as­sas­si­na­tion him­self. And Hol­i­day can’t quite bring him­self to ad­mit that Thiel’s war on Gawker didn’t fun­da­men­tally change the na­ture of the In­ter­net.

Thiel’s quest came up short in part be­cause his con­spir­acy fell prey to a risk that comes from not hav­ing to be pub­licly ac­count­able for your ac­tions: adopt­ing tac­tics or al­lies that un­der­cut the broader mis­sion. Thiel and his co- con­spir­a­tors were will­ing ben­e­fi­cia­ries of an In­ter­net- based con­tro­versy — Gamer­gate — that would make the way Gawker outed Thiel look pos­i­tively civ­i­lized.

Os­ten­si­bly a con­sumer move­ment op­pos­ing un­eth­i­cal videogame jour­nal­ism, Gamer­gate was sparked by a highly in­va­sive online rant writ­ten by the exboyfriend of a video- game de­signer named Zoe Quinn. Read­ers falsely sug­gested that Quinn had lever­aged a re­la­tion­ship with a Gawker me­dia writer for a pos­i­tive review of one of her games, lend­ing a watch-doggy gloss to an at­tempt by a man to take re­venge on a for­mer part­ner. Quinn was sub­ject to vi­o­lent threats and had to leave her home. The cam­paign of ha­rass­ment spread to other peo­ple who had ei­ther ad­vo­cated for or em- bod­ied di­ver­sity in the in­dus­try, or spo­ken up against Gamer­gate tac­tics. While Gawker Me­dia was far from Gamer­gate’s only tar­get, the move­ment opened up yet an­other front in the war on the com­pany’s cred­i­bil­ity.

Hol­i­day’s treat­ment of Gamer­gate in Con­spir­acy is trou­blingly brief. “Mr. A. claims that the con­spir­a­tors had noth­ing to do with start­ing Gamer­gate,” he writes, “but they un­doubt­edly fanned the flames.” This am­bi­gu­ity and se­cre­tive­ness should have prompted Hol­i­day to dig much deeper, rather than to ac­cept the con­spir­a­tors’ stonewalling. It mat­ters a great deal pre­cisely what the re­la­tion­ship be­tween the Thiel con­spir­acy and Gamer­gate was.

Even if the con­spir­a­tors merely watched from the side­lines as Gamer­gate ripped through the In­ter­net, the very ex­is­tence of Gamer­gate should have dis­proved Thiel’s nar­row be­lief that Gawker was the cause of all In­ter­net-based nas­ti­ness, call­ing into ques­tion whether the tar­get Thiel had cho­sen was ac­tu­ally the key to his larger goals. But if Thiel’s con­spir­a­tors had any con­tact with Gamer­gate — and Mr. A’s use of the phrase “largely au­tonomous but very help­ful” to de­scribe the re­la­tion­ship cer­tainly leaves open that pos­si­bil­ity — that would mean they were will­ing to work with peo­ple who made the In­ter­net nas­tier, more stupid, less truth­ful and — in the case of “swat­ting” at­tacks on Gamer­gate crit­ics — more dan­ger­ous.

And though his taste for con­spir­acy may have showed Thiel’s be­lief that it is im­por­tant to be able to scheme and act out of the pub­lic eye, it also gave the im­pres­sion that he had lots to hide. When he came for­ward af­ter the ver­dict to ac­knowl­edge that he had funded Bol­lea’s law­suit, it be­came clear that he had been plot­ting re­venge for nearly a decade - and that made him seem vin­dic­tive and ob­ses­sive.

Just be­cause Peter Thiel is a Sil­i­con Val­ley bil­lion­aire, his opin­ion does not trump our mil­lions of read­ers who know us for rou­tinely driv­ing big news sto­ries in­clud­ing Hil­lary Clin­ton’s se­cret email ac­count, Bill Cosby’s his­tory with women, the mayor of Toronto as a crack smoker, Tom Cruise’s role within Scientology, the N.F.L. cover-up of do­mes­tic abuse by play­ers. — Nick Den­ton

If he had been hid­ing this plot, what else might he be do­ing in the shad­ows? In 2016, jour­nal­ists jumped on re­marks Thiel had made about life ex­ten­sion tech­nolo­gies and sug­gested he was ex­plor­ing ways to har­vest the blood of the young to pro­mote his own longevity. It wasn’t true, but that didn’t pre­vent the story from tak­ing off. Thiel’s con­spir­acy against Gawker Me­dia seemed so im­plau­si­ble that the rev­e­la­tion of its ex­is­tence made every­thing else seem pos­si­ble.

Hol­i­day ac­knowl­edges Thiel learned “un­leash­ing such wild, chaotic forces is a dan­ger­ous bar­gain. Thiel might be gay, an im­mi­grant, lib­er­tar­ian, and gen­er­ally civ­i­lized and thought­ful, but the peo­ple on the alt-right he found him­self partly aligned with were not.” And Hol­i­day notes the case made Thiel a celebrity. But even as he al­lows for these caveats, Hol­i­day doesn’t reach the fi­nal, in­tel­lec­tu­ally hon­est con­clu­sion: that Thiel’s con­spir­acy was a fail­ure, not a suc­cess. To do so would be to ad­mit Con­spir­acy doesn’t come close to prov­ing Hol­i­day’s most am­bi­tious ar­gu­ment.

If trans­parency might have served Thiel bet­ter than con­spir­acy, Gawker’s stated val­ues might have saved the com­pany, too.

Hol­i­day writes that Dent on had sus­pi­cions t hat Bol­lea had a pow­er­ful fi­nan­cial backer, but the au­thor quotes for­mer Gawker ex­ec­u­tive ed­i­tor John Cook as say­ing, Den­ton “did not want to get wrapped in any kind of con­spir­acy the­o­ries.”

Had Gawker been able to chase down proof that Bol­lea’s law­suit was the work of an ex­traor­di­nar­ily wealthy man stew­ing over a smaller slight and re­ported that be­fore the case went to trial, it would have en­tered the arena on far dif­fer­ent terms. As Hol­i­day notes, break­ing that story would have bol­stered Gawker’s claim to be a se­ri­ous jour­nal­is­tic out­let.

Thiel him­self might have ben­e­fited from choos­ing trans­parency over con­spir­acy. The risk of pub­lic scru­tiny could have pre­vented his co-con­spir­a­tors from al­ly­ing, how­ever neb­u­lously, with Gamer­gate, a move that dam­aged Thiel’s cred­i­bil­ity and his stated ob­jec­tive of restor­ing san­ity to the in­ter­net. If, in­stead, Thiel had aligned him­self with the many, par­tic­u­larly fem­i­nists, talk­ing about the dan­gers of re­venge porn and a shrink­ing pri­vate sphere back in 2008 he could have given their mes­sage greater cred­i­bil­ity.

By the time Thiel did iden­tify him­self as Gawker Me­dia’s neme­sis af­ter the ver­dict in Bol­lea v. Gawker, the nar­ra­tive of the trial was well on its way to be­ing set. Thiel dis­cov­ered it’s dif­fi­cult to in­sist you’re the hero when you’ve al­ready won the sort of sur­pris­ing and dis­may­ing vic­tory that makes the pub­lic in­clined to believe that you’re the vil­lain.

“Cun­ning and re­sources might win the war,” Hol­i­day writes to­ward the end of Con­spir­acy, “but it’s the sto­ries and myths af­ter­wards that will de­ter­mine who de­served to win it.” The flaw in Thiel’s think­ing, and in Con­spir­acy, is in fail­ing to rec­og­nize that the sto­ries and the myths that emerge af­ter an event of­ten are the sub­stance of the vic­tory.


Hulk Ho­gan, whose real name is Terry Bol­lea, cen­tre, in court mo­ments af­ter a jury re­turned its 2016 de­ci­sion. Ho­gan sued Gawker for in­va­sion of pri­vacy and, bankrolled by tech bil­lion­aire Peter Thiel, won a $140-mil­lion judg­ment that led to Gawker’s bankruptcy.

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