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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.”

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John Freund

John Freund

Commercial

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Case Developments Commercial

Parabellum Capital Surfaces as Key Witness Falters in Goldstein Trial

By John Freund |

A pivotal prosecution witness in the federal criminal case against prominent Supreme Court advocate Tom Goldstein saw his credibility sharply undermined under cross-examination, raising new questions about the strength of the government’s case and the handling of key evidence.

Bloomberg reports that at the center of the dispute is Walter Deyhle, a former accountant who prepared Goldstein’s tax returns and testified for the government regarding alleged underreporting of gambling winnings. Under questioning from the defense, Deyhle acknowledged that his earlier statements to investigators conflicted with documentary evidence, including a contemporaneous email from Goldstein describing significantly higher gambling income than Deyhle had initially conveyed. The defense emphasized that these discrepancies were material, particularly given the government’s reliance on Deyhle to establish intent and knowledge in its tax-related charges.

The cross-examination also exposed admitted errors in Deyhle’s tax preparation work, further eroding his reliability in the eyes of the jury. Defense counsel argued that these mistakes, combined with incomplete or inaccurate recollections, weakened the foundation of the prosecution’s narrative and cast doubt on whether Goldstein knowingly misled tax authorities.

Compounding matters, the defense accused prosecutors of failing to timely disclose information related to a meeting in which the incriminating email was first presented to Deyhle. The alleged disclosure lapse prompted a dispute over the government’s evidentiary obligations, with the court ordering additional briefing to determine whether any remedial action is warranted.

The proceedings additionally brought attention to testimony from a senior executive at Parabellum Capital, the litigation finance firm that previously provided financial assistance to Goldstein. The testimony offered rare insight into the nature of the funding arrangement, which included support to address tax liabilities and personal financial pressures. While not accused of wrongdoing, the funder’s involvement illustrated how litigation finance can intersect with personal financial distress in high-stakes legal matters.

Commercial Regulatory Issues

Life After PACCAR: What’s Next for Litigation Funding?

By John Freund |

In the wake of the UK Supreme Court’s landmark R (on the application of PACCAR Inc) v Competition Appeal Tribunal decision, which held that many common litigation funding agreements (LFAs) constituted damages-based agreements (DBAs) and were therefore unenforceable without complying with the Damages-Based Agreements Regulations, the litigation funding market has been in flux.

The ruling upended traditional third-party funding models in England & Wales and sparked a wide range of responses from funders, lawyers and policymakers addressing the uncertainty it created for access to justice and commercial claims. This Life After PACCAR piece brings together leading partners from around the industry to reflect on what has changed and where the market is headed.

An article in Law.com highlights how practitioners are navigating this “post-PACCAR” landscape. Contributors emphasise the significant disruption that followed the decision’s classification of LFAs as DBAs — disruption that forced funders and claimants to rethink pricing structures and contractual frameworks. They also explore recent case law that has begun to restore some stability, including appellate decisions affirming alternative fee structures that avoid the DBA label (such as multiple-of-investment returns) and the ongoing uncertainty pending legislative reform.

Discussion also centres on the UK government’s response: following the Civil Justice Council’s 2025 Final Report, momentum has built behind proposals to reverse the PACCAR effect through legislation and to adopt a light-touch regulatory regime for third-party funders.

Commercial

Litigation Funding Founder Reflects on Building a New Platform

By John Freund |

A new interview offers a candid look at how litigation funding startups are being shaped by founders with deep experience inside the legal system. Speaking from the perspective of a former practicing litigator, Lauren Harrison, founder of Signal Peak Partners, describes how time spent in BigLaw provided a practical foundation for launching and operating a litigation finance business.

An article in Above the Law explains that Harrison views litigation funding as a natural extension of legal advocacy, rather than a purely financial exercise. Having worked closely with clients and trial teams, she argues that understanding litigation pressure points, timelines, and decision making dynamics is critical when evaluating cases for investment. This background allows funders to assess risk more realistically and communicate more effectively with law firms and claimholders.

The interview also touches on the operational realities of starting a litigation funding company from the ground up. Harrison discusses early challenges such as building trust in a competitive market, educating lawyers about non-recourse funding structures, and developing underwriting processes that balance speed with diligence. Transparency around pricing and alignment of incentives emerge as recurring themes, with Harrison emphasizing that long-term relationships matter more than short-term returns.

Another key takeaway is the importance of team composition. While legal expertise is essential, Harrison notes that successful platforms also require strong financial, operational, and compliance capabilities. Blending these skill sets, particularly at an early stage, is presented as one of the more difficult but necessary steps in scaling a sustainable funding business.