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

By John Freund |

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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ProLegal Unveils Full-Stack Legal Support Beyond Traditional Funding

By John Freund |

ProLegal, formerly operating as Pro Legal Funding, has announced a strategic rebrand and expansion that reflects a broader vision for its role in the legal services ecosystem. After nearly a decade in the legal finance market, the company is repositioning itself not simply as a litigation funder, but as a comprehensive legal support platform designed to address persistent structural challenges facing plaintiffs and law firms.

The announcement outlines ProLegal’s evolution beyond traditional pre-settlement funding into a suite of integrated services intended to support cases from intake through resolution. Company leadership points to longstanding industry issues such as opaque pricing, misaligned incentives, and overly transactional relationships between funders, attorneys, and clients. ProLegal’s response has been to rethink its operating model with a focus on collaboration, transparency, and practical support that extends beyond capital alone.

Under the new structure, ProLegal now offers a range of complementary services. These include ProLegal AI, which provides attorneys with artificial intelligence tools for document preparation and case support, and ProLegal Live, a virtual staffing solution designed to assist law firms with intake, onboarding, and administrative workflows.

The company has also launched ProLegal Rides, a transportation coordination service aimed at helping plaintiffs attend medical appointments that are critical to both recovery and case valuation. Additional offerings include a law firm design studio, a healthcare provider network focused on ethical referrals, and a centralized funding dashboard that allows for real-time case visibility.

Central to the rebrand is what ProLegal describes as an “Integrity Trifecta,” an internal framework requiring that funding advances meet standards of necessity, merit, and alignment with litigation strategy. The company emphasizes deeper engagement with attorneys, positioning them as strategic partners rather than intermediaries.

Litigation Funder Sues Client for $1M Settlement Proceeds

By John Freund |

A Croton-on-Hudson-based litigation financier has filed suit against a former client following a roughly $1 million settlement, alleging the funded party failed to honor the repayment terms of their litigation funding agreement. The dispute highlights the contractual and enforcement challenges that can arise once a funded matter reaches resolution.

According to Westfair Online, the financier provided capital to support a plaintiff’s legal claim in exchange for a defined share of any recovery. After the underlying litigation concluded with a significant settlement, the funder alleges that the plaintiff refused to authorize payment of the agreed-upon amount. The lawsuit claims breach of contract and seeks to recover the funder’s share of the settlement proceeds, along with any additional relief available under the agreement.

The case underscores a recurring tension within the litigation funding ecosystem. While funders assume substantial risk by advancing capital on a non-recourse basis, they remain dependent on clear contractual rights and post-settlement cooperation from funded parties. When those relationships break down, enforcement actions against clients, though relatively uncommon, become a necessary tool to protect funders’ investments.

For industry participants, the lawsuit serves as a reminder that even straightforward single-case funding arrangements can result in contentious disputes after a successful outcome. It also illustrates why funders increasingly emphasize robust contractual language, transparency around settlement mechanics, and direct involvement in distribution processes to reduce the risk of non-payment.

New Southeastern Laws Bring Litigation Funding Rules and Liability Insurance Changes

By John Freund |

New state laws taking effect across the Southeast at the start of 2026 include significant changes for insurers and litigation finance, with Georgia’s new restrictions on third-party funding standing out as particularly consequential for the legal funding industry.

Insurance Journal reports that in Georgia, newly effective legislation imposes a formal regulatory framework on litigation funders operating in the state. Funders are now required to register with the Georgia Department of Banking and Finance and disclose ownership information, including details related to foreign affiliations. The law also restricts funders from exercising control over litigation strategy, barring involvement in decisions such as attorney selection, settlement authority, or expert witness engagement. In addition, litigation funding agreements must be disclosed during discovery in civil cases, increasing transparency around third-party capital in litigation.

Beyond litigation finance, the Georgia law package includes changes affecting insurers, including provisions preventing auto insurers from canceling coverage or increasing premiums solely due to a failure to wear a seat belt. Other updates require certain home warranties, including heating and air-conditioning systems, to transfer automatically to new homeowners.

Elsewhere in the region, Florida enacted new requirements for pet insurers to provide clearer explanations of coverage terms and claim denials. Florida also implemented a law creating a public registry of individuals convicted of animal cruelty, which could influence liability and insurance disputes. South Carolina revised its liquor liability framework by reducing coverage requirements and limiting exposure for businesses found less than 50 percent at fault.