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The 6th Anniversary of the Peter Thiel / Hulk Hogan / Gawker Case: What Have We Learned?

The 6th Anniversary of the Peter Thiel / Hulk Hogan / Gawker Case: What Have We Learned?

This week marks the sixth anniversary of Terry Bollea (AKA professional wrestler Hulk Hogan) suing Gawker media for publishing a sex tape of him with a married woman. The suit made national news not just for its salacious nature—but because of the questions it raised regarding privacy versus journalistic freedom. Once news emerged that billionaire and PayPal co-founder Peter Thiel was funding Hogan’s claim, the case became even more sensational. In this piece, we’ll take a look at exactly what happened in the case, and how it impacted (or hasn’t impacted) Litigation Finance. The Facts of the Case In 2007, Gawker, a website known for celebrity scandals and salacious content, published a piece with the headline: “Peter Thiel is totally gay, people.” Was this newsworthy? Did the piece have journalistic integrity? Reasonable people can disagree. Peter Thiel is in fact gay, which means the truth of the article protected Gawker from a libel suit. In 2009, an outed Thiel gave an interview in which he called Gawker ‘destructive,’ even as he acknowledged that the site wasn’t focused on ruining him personally. Thiel also speculated that Gawker maintained a disdainful attitude toward Big Tech, and may be focusing on punishing industry leaders as a result. Fast forward to 2012, when Gawker published a lewd video featuring wrestler Hulk Hogan (AKA Terry Bollea) having sex with Heather Clem—wife of radio personality “Bubba the Love Sponge.” This led to Bollea suing the media outlet for infringement of rights of publicity, invasion of privacy, and intentional infliction of emotional distress. Bollea was represented by famed Los Angeles attorney Charles Harder. The published video, which Bollea claims was recorded without his knowledge or consent, contained a 2-minute section of a 30+ minute video—ten seconds of which included explicit sex acts. In 2016, Forbes magazine revealed that it was indeed Peter Thiel who was bankrolling Bollea’s case against Gawker. Speculation soared over what was viewed by many as Thiel’s revenge against Gawker for outing him. Did he want to ruin the media company, or purchase it, or simply malign the company that caused him personal and professional anguish? Thiel maintained that his involvement was philanthropic at heart, and meant to protect people from being bullied by unscrupulous media outlets. If anything, the lawsuit was meant to deter Gawker from intentionally releasing damaging content that lacked legitimate news value. Gawker founder Nick Denton, who was named personally in Bollea’s claim, made a statement about Thiel’s involvement in the case: “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.” Also in 2016, a jury awarded Bollea compensatory damages of $115 million, plus punitive damages of $25 million—finding Gawker liable. A few months later, Gawker filed Chapter 11 bankruptcy, and began looking for a buyer. Several media outlets owned by Gawker were sold. By November 2016, Gawker and Bollea reached a settlement of $31 million. Today, Gawker’s flagship gossip site is still active. Gawker media sold off several of its prominent sites including Gizmodo, Jezebel, Deadspin, and io9. The LF Connection The case itself was of particular interest in and around the Litigation Finance community. Opponents of third-party legal funding asserted that Thiel’s actions in the case laid out an effective blueprint for the very wealthy to bankroll frivolous, but eye-catching cases. Billionaires could, some posited, use their wealth and legal connections to target specific companies, forcing them into bankruptcy. This speculation took place alongside the typical accusations that third-party litigation funding could clog court dockets with meritless actions meant to be quick paydays for funders and their clients. For example, Peter Sheer, a First Amendment expert, suggested that Thiel and others might abuse the power of third-party legal funding to intimidate media outlets. According to Sheer: “Winning is the ultimate chilling effect, but if you can’t win the case, you at least want the editors to think twice before writing another critical story about you.” To the keen-eyed observer though, it’s clear that Peter Thiel neither incited this case, nor had any real control over its outcome. Bollea initiated the case before Thiel’s involvement. At the time the case was decided, the jury was unaware that Bollea had a benefactor. And since the jury ruled in favor of Bollea, not Gawker, it’s clear that the case had merit. Thiel was always adamant that funding Bollea’s case (to the tune of $10 million) was about deterrence, not revenge. He explains that he wanted to “fight back” against Gawker’s practice of damaging reputations and bullying those with no means to pursue a claim to conclusion. As Thiel explains, “…even someone like Terry Bollea, who is a millionaire and famous and a successful person didn’t quite have the resources to do this alone.” While one could view Thiel’s actions as being contradictory to the principles of free speech—he disagrees. In fact, Thiel has donated to free speech defenders like the Committee to Protect Journalists. Thiel maintains that there is a profound difference between journalism in the public interest, and the type of media Gawker traffics in. That’s why he decided to take action. Thiel told the New York Times, “It’s less about revenge and more about specific deterrence. I saw Gawker pioneer a unique and incredibly damaging way of getting attention by bullying people even when there was no connection with the public interest.” Now, six years after the case has concluded—what have we learned? We haven’t seen a rash of billionaires funding cases, frivolous or not, with the intention of bringing down specific companies. That’s not to say billionaires aren’t financing claims the way Thiel did, only that they aren’t doing so publicly. Unlike traditional litigation funders, Thiel did not stand to make any money from Bollea’s lawsuit. Technically, Thiel should still be considered the litigation funder, though his term sheet wouldn’t be one most funders would want to imitate. The Gawker case has not led to a slew of frivolous, funded claim. Among other reasons, it simply doesn’t make financial sense to invest in a case lacking in merit. Bollea’s accusations against Gawker were affirmed by the jury, which resulted in a large award. So this claim was meritorious, even if Thiel’s motivation for funding the claim were not ROI-based. Media outlets are not cowering en masse over fears of punitive lawsuits from billionaires. That was much ado about nothing. Holding media outlets accountable for what they print (and occasionally, their motivations for doing so) is a vital and essential part of the free press. Free speech is not freedom to print anything—even something as personal as a sex tape—merely as an attention-getting device. Final Takeaways Can a lawsuit fall under the purview of Free Speech? Thiel believes so, and many others agree. This case addressed questions of privacy, free speech, and litigation funding. The end results demonstrated that we are all entitled to some element of privacy—even the celebrities among us. The Gawker case also affirmed that litigation funding still serves the interests of justice by enhancing the ability of claimants to bring lawsuits when they are wronged. The takeaway here should be that Peter Thiel afforded Hulk Hogan access to justice. Of course, when a billionaire backs a professional wrestler against a media company, sometimes the moral of the story can get lost beneath the headlines.

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Legal Finance ABS for Institutional Investors: Market Securities Expands Offering

By Celso Filho |

The following article was contributed by Celso Filho, Global Head of Special Projects at Market Securities, and co-founder and CEO of Rachel AI.

Life insurers and other institutional investors face a structural allocation challenge: securing sufficient volumes of rated, long-duration, yield-bearing assets to match long-tail liabilities. Public investment-grade bond markets remain large, but they do not consistently provide the spread, structure, or customization required. As a result, insurers have steadily increased allocations to private placements, asset-backed securities, and other forms of private credit.

According to Milliman's 2026 analysis of NAIC statutory filings, private bonds now account for approximately 46% of U.S. life insurers' bond portfolios — up from 29% a decade ago — reflecting a sustained and accelerating shift toward alternative sources of yield and duration. The trend is sharpest among PE-owned life insurers, where structured securities account for approximately 49% of total bonds — underscoring how deeply the search for rated, yield-bearing paper has become embedded in the asset allocation strategies of the most capital-active players in the sector.

Market Securities is addressing that demand by bringing to market asset-backed securities backed by legal finance receivables, including pre-settlement plaintiff advances and receivables linked to contingent fee arrangements with law firms. These assets introduce a distinct return profile driven by legal case cash flows rather than traditional corporate credit cycles, and they can be structured into rated securitizations suitable for institutional portfolios.

The opportunity is crystallizing across three investor tiers — each approaching the asset class from a different angle, but converging on the same structure and, together, driving the institutionalization of legal finance.

  1. Insurers and other rated-mandate investors represent the largest pool of demand. Operating within strict capital and rating constraints, they allocate to investment-grade instruments at 125 to 200 basis points over Treasuries and can deploy hundreds of millions per transaction. Their participation defines the scale of the opportunity — and creates the demand for rated, structured exposure that legal finance ABS is uniquely positioned to meet.
  2. Private credit managers, sovereign wealth funds, and large family offices occupy the senior and mezzanine tranches, targeting enhanced yield with structural protections. Unlike insurers, these investors are not dependent on ratings and underwrite assets directly, focusing on risk-adjusted returns, structure, and downside protection. They provide the capital depth required to scale transactions and anchor issuance.
  3. Specialist legal finance investors sit in the junior and equity tranches, underwriting legal risk directly and targeting returns in excess of 25%. These investors take first-loss positions, pricing legal risk at the asset level — and for them, securitization offers a compelling strategic advantage: lower cost of capital and greater leverage availability than traditional fund formation, particularly relevant in today's challenging fundraising environment.

These tiers are complementary rather than competitive. Rated investors bring scale and duration demand; private credit and sovereign capital provide flexible, non-rating-constrained liquidity; and specialist managers contribute underwriting expertise and first-loss alignment. Securitization is the architecture that aligns them — converting legal finance receivables into a format that institutional capital can size, rate, and deploy against.

Market Securities sees this convergence as structural rather than cyclical, and legal finance ABS as the mechanism through which it becomes permanent.

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Celso Filho, CFA, CAIA is Global Head of Special Projects at Market Securities, based in the Dubai International Financial Centre (DIFC). He is also co-founder and CEO of Rachel AI, a London-incorporated litigation finance technology and analytics platform. Celso began his career as a lawyer, practising for seven years before transitioning into investment banking and specialty finance, with prior roles at Citigroup and Credit Suisse. He holds an MBA from INSEAD.

LITFINCON Announces European Debut With Amsterdam Summit

By John Freund |

The global litigation finance conference series LITFINCON is expanding to Europe, with organizer Siltstone Capital announcing a two-day summit at the Rosewood Amsterdam on October 7–8, 2026.

As reported by PR Newswire, LITFINCON Europe will bring together litigation funders, law firms, institutional investors, and general counsels for eleven panels covering topics ranging from regulatory divergence across the UK, EU, and U.S. to deal mechanics, AI adoption, and developments at the Unified Patent Court. The conference will close with a 75-minute unscripted "Candid Conversations" session.

"Capital is flowing into the space at an unprecedented rate, and the demand for high-quality, senior dialogue has never been higher," said Robert Le, co-founder of Siltstone Capital. Jim Batson, the firm's CIO for legal finance, added that "LITFINCON has built its reputation on bringing the right people into the right room."

The Amsterdam venue — a set of five interconnected 19th-century palace buildings along the Herengracht canal that once served as the city's main courthouse — marks a fitting location for the conference's European launch. The Rosewood Amsterdam's historic connection to the Dutch judicial system underscores the growing intersection of legal proceedings and institutional capital on the continent.

LITFINCON originated in Houston and has rapidly scaled into a multi-city global series. The European debut follows LITFINCON Asia, scheduled for June 4, 2026, at Marina Bay Sands in Singapore. Sponsorship, speaking opportunities, and registration are now available at litfinconeurope.com.

Fintechs Target Estate Disputes as Baby Boomer Wealth Transfer Fuels Litigation Funding Demand

By John Freund |

A wave of fintech startups is moving into the estate and probate space, offering litigation funding and technology solutions for executors navigating the spiralling costs of administering deceased estates.

As reported by the Australian Financial Review, with a $5.4 trillion Baby Boomer wealth transfer now underway, legal sector disruptors are positioning themselves to capitalize on the growing complexity and expense of settling estates. The report highlights how litigation funding is extending into probate and succession disputes, a segment that has historically been underserved by traditional funders.

The trend reflects a broader expansion of the litigation finance market beyond its traditional strongholds in commercial disputes and class actions. Estate litigation is expected to surge as record intergenerational wealth transfers generate contested wills, disputed charitable bequests, and family succession battles. In Australia alone, the over-60 population is projected to pass on $3.5 trillion to younger generations over the next two decades.

For litigation funders, estate disputes present an attractive proposition: cases with quantifiable asset pools, clear legal frameworks, and relatively predictable timelines compared to large-scale commercial litigation. The entry of technology-driven players into this space signals a new frontier for the industry as it continues to diversify its portfolio of funded case types.