Conspiracy - Book Summary

Dive into the demise of Gawker Media: a saga of revenge, wealth and a wrestling legend

The year was 2016, and the news headlines were dominated by a strange case: Hulk Hogan, the former wrestling superstar, was embroiled in a lawsuit with notorious online gossip platform, Gawker. You may be familiar with the outcome—Hogan's victory and the subsequent bankruptcy of Gawker. But have you ever wondered about the unseen machinery behind this monumental downfall?

Today, we'll take you on a journey into the shadowy corridors of this jaw-dropping saga, orchestrated by none other than the billionaire tech mogul, Peter Thiel. With an astonishing display of invisible power, Thiel managed to crumble Gawker's foundations, revealing a high-stakes plot straight out of a Hollywood blockbuster. We'll unravel Thiel's deep-rooted animosity toward Gawker and the cloak-and-dagger tactics that led to its eventual capitulation.

Additionally, we'll delve into the contentious debate about Thiel's indirect meddling in Hogan's lawsuit, and shed light on the circumstances that led to Gawker's controversial court proceedings.

In this narrative, you will discover:

The genesis of Peter Thiel's venomous enmity towards Gawker,

The bizarre intersection of a celebrity sex tape and this intricately woven conspiracy,

The meticulous orchestration of a few individuals determined to topple a media titan.

A perceived privacy breach in 2007 ignited a long-lasting feud.

Every monumental saga starts with a seemingly insignificant spark. In this case, it was a 400-word blog post in 2007, exposing the sexual orientation of a certain tech tycoon, Peter Thiel. It was this tiny spark that ignited a nine-year, multi-million-dollar conspiracy.

To truly grasp the monumental implications of this seemingly innocuous blog post, we must delve into the profiles of both the subject, Peter Thiel, and the publisher, Gawker Media.

Let's acquaint ourselves with Peter Thiel first.

Even in 2007, Thiel had etched his name as an influential entrepreneur. Known as one of the masterminds behind the popular online payment system PayPal, he was also recognized as Facebook's first significant investor. Although he had privately come out to those close to him, Thiel was rather discreet about his sexuality in public circles, favoring to maintain an aura of ambiguity around his personal life in the tech world of Silicon Valley.

Then there's the platform that sparked the fire—Valleywag. Ostensibly a tech-news platform, Valleywag was an offshoot of its notorious parent gossip blog, Gawker Media, both brainchildren of British-born tech-entrepreneur, Nick Denton.

Denton may have found his initial success in the tech realm, but his true passion was indulging in the revelry of secrets and gossip. He found immense satisfaction in airing the well-guarded secrets of others to the world, especially if those 'others' were the rich and powerful, all in the name of 'transparency' and 'entertainment'.

Under Denton’s direction, a zealous team of writers with an inclination for biting wit and a knack for sarcastic tones eagerly dismantled the façade of public figures and institutions, unearthing any hidden hypocrisies. And the public loved it. Denton's websites raked in $120,000 in advertising revenue every month by 2005, and by 2012, Gawker's annual revenues had skyrocketed to an impressive $40 million.

But even with his cunning media instinct, Denton made a dire miscalculation in 2007, when he decided to pry into the personal life of Peter Thiel.

A direct confrontation ignites Peter Thiel's simmering resentment against Gawker's invasive practices.

Peter Thiel's aversion for Gawker Media was etched on December 19, 2007. It was on this date that a blog post under the headline, "Peter Thiel is totally gay, people," was published on the Valleywag website. But was this single post the sole reason for Thiel's animosity, or was there more to his displeasure? To truly fathom the extent of Thiel's antipathy, we need to delve into the sociocultural environment of 2007 and scrutinize other articles that Gawker churned out during that time.

From our modern perspective, it may seem odd that a gay man would feel the need to hide his sexual orientation. Yet, we must remember that the world in 2007 was much less accepting of homosexuality. It would take five more years for then-President Obama to publicly endorse gay marriage and another year for Hillary Clinton to follow suit. In a world teetering on the brink of acceptance, Thiel saw the Valleywag article as an invasion of his privacy.

But Gawker Media's intrusions into Thiel's personal life didn't end there. Later that same year, Valleywag proceeded to publish additional blogs about Thiel, including one revealing his boyfriend's identity. Consequently, Gawker Media's articles about Thiel in 2007 and 2008 accumulated around 500,000 views, catapulting the ordinarily private Thiel and his personal life into the limelight.

Despite the apparent malice towards Thiel, such behavior was par for the course for Gawker Media. They had built their reputation on their readiness to run pilfered content and publish anonymous leaks. Back in 2005, they published a stolen sex tape of Fred Durst, lead singer of Limp Bizkit, showcasing their willingness to cross boundaries that traditional media organizations would hesitate to breach. Any attempt to retaliate against Gawker was met with even more ridicule, under the guise of the United States' robust free-speech laws.

Understanding Gawker's shock-and-awe strategy, Thiel started referring to the media company as MBTO, an acronym for "Manhattan Based Terrorist Organization." Thus, Thiel was galvanized into action, ready to challenge the seemingly invincible media behemoth.

A daunting task: Thiel's calculated strategy to challenge the seemingly invincible Gawker.

In the period from 2008 to 2011, Peter Thiel mulled over possible countermeasures against Gawker Media's relentless proclivity for public humiliation. However, striking back at Gawker was a monumental task. After all, there's a longstanding axiom that advises against picking a fight with someone who buys ink by the barrel — or, in other words, don't engage in conflict with the press.

Indeed, Thiel might have been a billionaire blessed with remarkable intellect, but even his closest allies held reservations about his chances of toppling Gawker Media.

Why did Gawker seem so unbeatable?

The first hurdle was America’s First Amendment, granting journalists near-impervious legal immunity against legal action arising from unpleasant revelations. This posed a considerable obstacle to those aspiring to pursue legal action against them.

Secondly, shaming Gawker Media seemed a futile pursuit. A direct confrontation with Gawker's founder, Nick Denton, accusing his company of bullying would likely result in even more vitriolic content targeted at Thiel. Gawker would have reveled in the drama and attention that a public feud with a billionaire would undoubtedly generate.

Lastly, Thiel simply couldn't acquire Gawker Media and reroute its editorial course. It was an independent entity, beholden to no one but Denton himself — and Denton had no intention of parting ways with his media dominion.

Despite these seemingly insurmountable barriers, Peter Thiel was not one to surrender. In 2011, he devised a tactical maneuver to dismantle his adversary.

In collaboration with a promising business associate — referred to by the author solely as Mr. A — Thiel conceived a plan to establish a shell company dedicated to a singular purpose. Under Mr. A's leadership, the company would discreetly hire investigative journalists and legal experts. Their assignment? To comb through thousands of Gawker articles in search of any evidence of illicit activities on Gawker's part.

Significantly, Mr. A and his team decided to focus exclusively on infringements unrelated to freedom-of-speech laws, understanding the formidable challenge of winning such cases in the American judicial system.

Nevertheless, if Gawker had faltered in any other legal sphere, Peter Thiel intended to leverage it. If their investigative team could unearth something legally substantial, Thiel and Mr. A would sue Gawker into nonexistence.

Thiel's moment of action: Hulk Hogan's lawsuit against Gawker offers a unique opportunity.

As the investigation spearheaded by Mr. A continued to reveal Gawker's questionable practices, Thiel's conviction that Gawker needed to be toppled only deepened. The gossip site seemed to have no boundaries, even publishing unauthorized nude pictures of famous women. However, the million-dollar question remained — what charges could Thiel and his legal team successfully lodge in a court of law?

As fate would have it, the perfect opportunity came knocking in 2012.

Professional wrestler and actor Terry Bollea, better known as Hulk Hogan, found himself in the line of fire of Gawker’s unrestrained expose journalism. A few years earlier, Hogan was unknowingly recorded engaging in sexual acts with his best friend's wife. This secretly-recorded footage was handed over anonymously to Gawker in 2012, and without any hesitation, the company made it public on its website. Aghast and humiliated, Hogan immediately issued a cease-and-desist letter to Gawker through his legal team, emphasizing that the tape was recorded without his consent and threatening legal action if the tape wasn't removed.

Predictably, Gawker remained defiant, leaving Hogan with no choice but to prepare for a legal battle.

Thiel and Mr. A, alongside their legal council, recognized this as the long-awaited chance to strike at Gawker. Hogan's impending lawsuit against Gawker was not about challenging the United States' free-speech laws; rather, it was a matter of infringed privacy rights. These might appear similar but are in fact two distinct legal concepts. The odds of winning a lawsuit centered around privacy violations were significantly higher than one based on free speech.

Eager to seize this golden opportunity, Mr. A approached Hogan with an enticing proposal — would he be interested in suing Gawker with the financial backing of a mysterious third party? Thiel was insistent that his involvement remain under wraps. If Gawker discovered his involvement, they would undoubtedly unleash their full wrath of scandalous rumors against him. The potential harm to his reputation could be catastrophic.

Luckily, Hogan wasn't bothered about knowing the identity of his unexpected patron. His sole focus was to have the illicit tape taken off Gawker's website.

Suddenly, Peter Thiel was on the verge of the legal showdown he had been eagerly anticipating with Gawker.

Gawker's fatal underestimation: It dismissed Hulk Hogan's lawsuit until the last moment.

In 2016, Peter Thiel's carefully laid strategy to strike at Gawker came to a head when a court permitted Hulk Hogan to sue Gawker for a staggering 100 million dollars in damages. This was it - Bollea versus Gawker was going to a jury.

At this stage, one might expect that Gawker Media and its CEO, Nick Denton, were starting to panic. However, the reality was startlingly different — Gawker didn’t seem particularly worried.

Gawker and Denton showed a remarkable level of nonchalance up until the commencement of the court case with Hogan. One major reason for this seeming indifference was that they were oblivious to the fact that Hogan's legal bills were being footed by a billionaire. Instead, they wrongly assumed that Hogan, a mere millionaire, was covering his own legal expenses. Gawker, having insurance coverage for its legal fees, figured that Hogan would run out of funds to sustain a lengthy legal battle.

Operating under this misconception, Denton and his legal team were convinced that Hogan would eventually settle the case outside of court, probably for a sum far below the demanded 100 million dollars.

Much to Gawker’s misfortune, they grossly underestimated Hogan. When Gawker finally proposed a settlement just as the case was due in court, it offered Hogan 10 million dollars - but no apology. Fueled by unlimited financial resources, Hogan adamantly rejected the settlement.

Gawker was soon to pay the price for its previous dismissive attitude.

As Bollea versus Gawker was presented to a jury, Gawker found itself in a precarious position. Gawker had overlooked the fact that the case was being tried in Florida, a hometown ground for Hogan, a far cry from their New York City audience. The Florida jury, composed of Hogan's fellow citizens, revered their local celebrity. When Gawker Media's lawyers made an attempt to defend the derogatory articles and leaked sex tape as expressions of free speech, their justification fell on unsympathetic ears. The jury viewed their beloved local icon being unjustly maligned by a group of outsiders, projecting an air of cruel hipster disdain.

In March 2016, the verdict was announced — the jury sided with Hogan, awarding him a staggering 140 million dollars in damages. Thanks to Peter Thiel's calculated strategy and dogged persistence, Gawker's reign of scandalous revelations was over.

How Hogan's lawsuit led to Gawker's financial ruin and caused a media backlash against Peter Thiel.

When a court decrees that you and your company owe $140 million in damages, what course do you pursue? Well, if you're in the same boat as Nick Denton and own an independent company like Gawker, the likely path would be to declare bankruptcy and close down your business.

However, even though this outcome should have delighted Peter Thiel, it proved a double-edged sword.

Shortly after the verdict, Thiel was revealed as the financial angel behind Hulk Hogan's legal battle. During the trial, Thiel had been careful to keep his involvement under wraps, disclosing it to hardly anyone. However, following the victory, the desire to revel in his success got the better of him. He divulged the secret to a few close friends and soon enough, news about his role in the Gawker case made international headlines.

Despite his careful planning and anticipation of all possible outcomes, Thiel was not prepared for what was to follow. His revelation triggered a massive backlash from America's media fraternity. Initially, many journalists had welcomed the verdict against Gawker, but once Thiel's role was exposed, they quickly altered their stance. The narrative shifted dramatically — Thiel was now painted as a vindictive billionaire engaging in petty retaliation against an audacious media underdog, posing a threat to the freedom of speech.

Thiel was taken aback and disoriented by the vehement backlash. In his mind, his actions were philanthropic in nature. He perceived his victory as a triumph over a relentless media bully, on behalf of average Americans, especially those lacking the resources to defend their rights against the media onslaught.

Did his perception align with reality? The author leaves the answer to this question to the readers' discernment. However, here are a few factors to consider before forming an opinion.

Thiel may have operated covertly, but there was nothing unlawful about his actions. Given his vast resources, his commitment to stay entirely within legal boundaries speaks volumes about his ethical standpoint.

In conclusion, the author leaves the reader with a thought — to orchestrate Gawker's collapse, Thiel demonstrated a remarkable amount of long-term focus, personal determination, and a refusal to yield to the prevailing norm. Arguably, these traits played a crucial role in his victory, just as his wealth did. In today's politically unsettled times, when the status quo can often be unsettling, perhaps there is a lesson to be learned from Peter Thiel's patient and strategic maneuvers. Perhaps we need more conspiracies, not fewer, if we truly wish to effect change in the world.

Wrapping it up

Spanning nearly a decade, Peter Thiel's intricate plan to obliterate Gawker ended up draining his pockets to the tune of about $10 million. This saga began with a brief blog post that exposed Thiel's sexuality, unfurled into a legal battle featuring a professional wrestler, and culminated in the financial ruin of a prominent and feared online publishing entity. Regardless of one's perspective on Thiel's actions — be it right or wrong — one cannot deny the audacity and scale of his carefully orchestrated conspiracy, making it one of the most daring schemes of our era.