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

By John Freund |
March 12, 2025

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

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.”

About the author

John Freund

John Freund

Commercial

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Commercial

Avoiding Pitfalls as Litigation Finance Takes Off

By John Freund |

The litigation finance market is poised for significant activity in 2026 after a period of uncertainty in 2025. A recent JD Supra analysis outlines key challenges that can derail deals in this evolving space and offers guidance on how industry participants can navigate them effectively.

The article explains that litigation finance sits at the intersection of law and finance and presents unique deal complexities that differ from other private credit or investment structures. While these transactions can deliver attractive returns for capital providers, they also carry risks that often cause deals to collapse if not properly managed.

A central theme in the analysis is that many deals fail for three primary reasons: a lack of trust between the parties, misunderstandings around deal terms, and the impact of time. Term sheets typically outline economic and non-economic terms but may omit finer details, leading to confusion if not addressed early. As the diligence and documentation process unfolds, delays and surprises can erode confidence and derail negotiations.

To counter these pitfalls, the piece stresses the importance of building trust from the outset. Transparent communication and good-faith behavior by both the financed party and the funder help foster long-term goodwill. The financed party is encouraged to disclose known weaknesses in the claim early, while funders are urged to present clear economic models and highlight potential sticking points so that expectations align.

Another key recommendation is ensuring all parties fully understand deal terms. Because litigation funding recipients may not regularly engage in such transactions, well-developed term sheets and upfront discussions about obligations like reporting, reimbursements, and cooperation in the underlying litigation can prevent later misunderstandings.

The analysis also underscores that time kills deals. Prolonged negotiations or sluggish responses during diligence can sap momentum and lead parties to lose interest. Setting realistic timelines and communicating clearly about responsibilities and deadlines can keep transactions on track.

Commercial Regulatory Issues

Labour MP Comes Out Swinging Against Litigation Funding

By John Freund |

Litigation funding has become a fixture in modern civil justice systems, designed to open the courts to claimants who lack the means to pursue meritorious claims. But a recent opinion piece by Labour MP Oliver Ryan argues that in the UK, the industry is increasingly drifting from that core purpose and instead serving the financial interests of investors and funders at the expense of real victims.

An article in City A.M. states that while third-party litigation funding has a legitimate role in enabling access to justice, market incentives are now skewing the system. Ryan highlights examples including the UK government’s move to “protect litigation funding” and reverse the Paccar ruling—a Supreme Court decision that had cast doubt on traditional fee structures—arguing that policy solutions must reflect how the market actually operates on the ground, not just how policymakers hope it will.

Ryan points to the handling of the Post Office scandal as a stark case in point. Despite grievous harms suffered by sub-postmasters, he notes that approximately 80 percent of damages paid eventually flowed to funders and lawyers rather than victims—an outcome he says “cannot be right.” He also cites the collapse of a cavity insulation claim and management upheavals in a multi-billion-pound class action against BHP as examples of how funder-centric incentives can undermine claimant outcomes and system integrity.

Rather than calling for an end to litigation funding, Ryan urges reforms centered on capping excessive funder returns, enforcing capital adequacy protections for claimants, tightening marketing oversight, and rebalancing incentives so victims—not investors—are the primary beneficiaries of successful claims.

Case Developments Commercial

Private Investors Eye Profits in L.A. County Sex Abuse Settlements

An investigation reveals that private investors are positioning themselves to profit from the enormous pool of money flowing from Los Angeles County’s historic sex abuse litigation. The county has already agreed to spend nearly $5 billion this year resolving thousands of claims related to alleged sexual abuse in its juvenile detention and foster care systems, including a $4 billion settlement—the largest of its kind in U.S. history.

An article in the Los Angeles Times explains that proponents of this investor involvement argue such financing gives plaintiffs’ attorneys the capital they need to take on deep-pocketed defendants and helps victims who lack resources access justice. Records reviewed by the Times show that several law firms bringing these claims receive financial backing from private investors, often through opaque out-of-state entities and Delaware-based companies.

Backers contend the arrangement can level the legal playing field and expedite case filings and settlements. However, public officials and critics express alarm over the lack of transparency surrounding these investments and the possibility that significant portions of settlement money intended for survivors could instead flow to private financiers. Some county supervisors reported being contacted by investors asking about the potential profitability of the sex abuse suits, raising ethical concerns about treating human trauma as an “evergreen” revenue stream.

The backdrop to this investor interest is a surge in litigation following changes in California law that revived long-dormant abuse claims and spurred widespread advertising by plaintiff firms seeking new clients. Government scrutiny has heightened amid reports of questionable recruitment practices and potential fraud in some claims, and the county’s district attorney has launched an investigation into parts of the settlement process.