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Community Spotlight:  Stephen Kyriacou, Head of Litigation and Contingent Risk Solutions, Willis Towers Watson

By John Freund |

Stephen is a seasoned litigation and contingent risk insurance broker and former practicing complex commercial litigator who joined WTW in February 2025 as Head of Litigation and Contingent Risk Insurance.  In his role, Stephen evaluates litigation-related risks and structures bespoke litigation and contingent risk insurance policies for litigation finance, hedge fund, private equity, law firm, and corporate clients. 

Prior to joining WTW, Stephen was a Managing Director and Senior Lawyer in Aon’s Litigation Risk Group.  Stephen joined Aon in 2019, and was the first insurance industry professional dedicated solely to the litigation and contingent risk insurance market, leading the Litigation Risk Group’s origination and business development work, in-house legal diligence, efforts to advocate for coverage with underwriters, and negotiation and structuring of insurance policies.  During his time at Aon, Stephen was a three-time Risk and Insurance Magazine “Power Broker” (2022, 2023, 2024); spearheaded the development of judgment preservation insurance and insurance-backed judgment monetization as well as the synergy of litigation and contingent risk insurance with litigation finance; and was responsible for placing billions of dollars in total coverage limits – including the largest ever litigation and contingent risk insurance policy, and several policies that each provided over $500 million in coverage limits – and delivering hundreds of millions of dollars in premium to insurers.  Stephen additionally provided consulting and broking services on litigation-driven, insurance capital-based investment opportunities and sales of litigation claims, insurance claims, and subrogation rights as part of the Aon Special Opportunities Group.

Prior to joining the insurance industry, Stephen was a complex commercial litigator in the New York City office of Boies, Schiller & Flexner from 2011 to 2019.  While at BSF, Stephen amassed significant trial, appellate, and arbitration experience representing both plaintiffs and defendants in the U.S. and abroad across a wide array of practice areas, including securities, antitrust, constitutional, insurance, first amendment, employment, government contracting, and criminal law, as well as in multidistrict and class action litigation.  Stephen’s clients included banks and other major financial institutions, private equity firms, technology companies, foreign sovereigns, professional sports teams, television networks, insurance companies, corporate executives, and other high-net-worth individuals.  

Stephen earned his J.D. from the New York University School of Law in 2010, and is a member of the New York State Bar.  He also clerked for the Honorable Tanya S. Chutkan in the United States District Court for the District of Columbia.

Company Name and Description:  Willis Towers Watson

Company Website: https://www.wtwco.com/en-us

Headquarters:  Stephen is based in New York

Area of Focus:  Litigation and contingent risk insurance for litigation finance, hedge fund, private equity, law firm, and corporate clients

Member Quote:  “I have been working with litigation finance firms to insure their litigation-related investments since I first entered the insurance industry in 2019, and I view litigation finance and funder-backed plaintiff-side litigation as the most important growth areas for the litigation and contingent risk insurance market, as well as the areas where coverage can be most value additive for clients. 

I have also been bringing litigation finance firms into insurance transactions as financing counterparties since I first devised the concept of insurance-backed monetization for judgment preservation insurance clients back in 2020, which concept has since expanded to the point where litigation finance capital has become inexorably intertwined with all forms of plaintiff-side insurance coverage.  

As the market for this insurance pivots away from single-case risks and towards portfolio-based policies for litigation finance firms and the law firms that they fund, litigation finance clients can trust that WTW will be at the forefront of innovating new coverage structures and concepts to address their unique risk management needs and ambitious financial goals, will deliver best-in-class client service utilizing our incomparably strong and longstanding relationships with underwriters, and will be a vocal champion of litigation finance both within and outside of the insurance industry.”

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John Freund

John Freund

Commercial

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Case Developments Commercial

Apple Denied Access to Litigation Funding Records in Patent Dispute

By John Freund |

In a closely watched decision, a federal judge has denied Apple’s attempt to compel Haptic Inc. to turn over litigation funding records in an ongoing patent infringement case.

According to Bloomberg Law, the dispute centers on Haptic’s claims that Apple’s iPhone “Back Tap” feature infringes on its patented technology. As part of its defense, Apple sought disclosure of communications between Haptic and its third-party funders, arguing the materials could reveal improper influence or strategic coordination.

The court, however, ruled in favor of Haptic, holding that the requested documents are protected under the work-product doctrine. This legal principle shields materials prepared in anticipation of litigation from disclosure, unless the opposing party demonstrates a substantial need. The judge emphasized that Apple had not met that burden, noting that the funder’s role did not compromise the independence of Haptic’s legal counsel or litigation strategy.

This decision is the latest in a series of rulings that underscore courts’ growing acceptance of litigation funding as a legitimate component of the civil litigation system. It also highlights the increasing legal clarity around funder-client relationships, especially regarding privilege and disclosure.

Commercial Regulatory Issues

Triple-I Ties Litigation Funding and Legal Ads to Soaring Insurance Costs

By John Freund |

A new report from the Insurance Information Institute (Triple-I) is drawing attention to the growing intersection between third-party litigation funding, mass tort advertising, and rising insurance costs. The report argues that these trends are correlated and may also be fueling a cycle of litigation abuse that places upward pressure on insurance premiums across the country.

According to Insurance Journal, the Triple-I report signals growing concern among insurers about the litigation finance industry’s systemic impact on claim costs and rate-setting. The report claims that attorney advertising—often funded or indirectly supported by litigation financiers—has surged in recent years, particularly in areas like product liability, pharmaceuticals, and toxic exposure. The influx of cases, many involving large aggregations of claims, has increased both the frequency and severity of insurance payouts. Triple-I warns that this dynamic contributes to a “social inflation” effect, where legal costs outpace economic fundamentals.

The report calls for regulatory action and transparency, suggesting that clearer disclosure rules around third-party funding and advertising could help insurers, courts, and the public better assess the risks and incentives involved.

While the litigation finance industry has long argued that its capital helps level the playing field for under-resourced claimants, critics say the unchecked expansion of funding models and advertising tactics may tilt the balance toward profit over merit.

Case Developments Commercial

Steward Health Wins Court Approval for $127 Million Loan to Fund Insider Litigation

By John Freund |

A U.S. bankruptcy judge has approved Steward Health Care System’s request to obtain a $127 million loan to fund litigation against its former executives and insiders. The embattled hospital operator, which filed for bankruptcy earlier this year, is targeting up to $2 billion in potential recoveries through legal action.

The financing arrangement—approved despite objections from several creditors—marks a critical step in Steward’s restructuring strategy, enabling the hospital network to pursue claims of mismanagement, breach of fiduciary duty, and possible fraudulent conveyances by former leadership. The proposed defendants in the litigation include members of Steward’s former executive team and affiliated entities involved in its rapid expansion and subsequent financial unraveling.

The loan is being provided by a group of new money lenders who will receive top-tier repayment priority from any litigation proceeds, a provision that stirred concern among some creditor groups during court proceedings. Critics argued the structure could reduce recovery prospects for unsecured creditors. However, the judge determined that the funding was both necessary and appropriately structured to pursue high-value claims that could ultimately benefit the estate.

Legal analysts note that this type of debtor-in-possession (DIP) financing for litigation expenses is becoming more common in large corporate bankruptcies, especially when internal mismanagement or fraud is suspected. For litigation funders and investors in legal finance, the Steward case underscores the growing intersection of bankruptcy proceedings and asset recovery litigation.