As insurers search for yield in an era of capital pressure and volatile markets, many have outsourced large portions of their balance sheets to specialist asset managers promising sophistication, diversification, and access to complex credit.
The pitch is familiar: insurers stay focused on underwriting while external managers generate returns through insurance-linked securities, private credit, and bespoke structures. But a growing number of failures suggest a big risk of this model is still poorly understood. When insurers outsource asset management, they also outsource judgment.
The recent history of Leadenhall Capital Partners offers a cautionary case study. Founded in 2008, London-based Leadenhall positions itself as a specialist in insurance-linked investments, spanning catastrophe bonds, collateralized reinsurance, life and health-linked risk transfer, and insurance-adjacent private credit. The firm operates as a joint venture connected to Japan’s MS&AD insurance group, with regulatory registrations in the UK, the U.S., and Bermuda.
On paper, Leadenhall looks like an ideal outsourced partner for insurers: sector focus, regulatory oversight, and roughly $4 billion to $5 billion in assets under management.
Yet across a series of high-profile situations—Friday Health Plans, Health IQ, Reverse Mortgage Investment Trust, and ongoing litigation involving 777 Partners and A-CAP—a consistent pattern emerges: aggressive capital deployment into complex or regulated businesses, followed by slow recognition of distress, litigation-heavy responses and substantial value erosion.
Friday Health Plans was once hailed as a fast-growing disruptor in the Affordable Care Act marketplace. Between 2021 and 2022, the insurer expanded rapidly across multiple states, raised hundreds of millions of dollars and projected nearly $2 billion in annual premium revenue.
Leadenhall provided debt financing, led later funding rounds and publicly endorsed Friday’s management and growth strategy. But by late 2022, warning signs were hard to miss. Friday began exiting states, laying off employees and drawing increased scrutiny from insurance regulators.
In 2023, the collapse accelerated. Texas placed Friday into liquidation. Georgia declared it insolvent. Oklahoma imposed regulatory supervision. By mid-year, the company had terminated its workforce and transferred assets for liquidation. Court filings later revealed that Friday was so depleted it struggled to maintain legal representation in post-collapse litigation.
For insurers, the lesson was stark: repeated capital injections did not prevent failure in a tightly regulated business where execution missteps compound quickly. Growth capital, even from insurance-focused investors, isn’t a substitute for operational discipline.
Health IQ followed a different trajectory but reached a similar end. Once valued at roughly $450 million and backed by prominent venture investors, the insurance brokerage pivoted repeatedly—from life insurance to Medicare sales—while relying heavily on commission revenue and aggressive telemarketing.
By December 2022, Health IQ conducted mass layoffs, triggering WARN Act litigation. In 2023, the company filed for bankruptcy with liabilities vastly exceeding its assets. Creditors declined to support a Chapter 11 restructuring, and Health IQ moved directly into liquidation.
Media coverage detailed unpaid vendors, dozens of lawsuits, and millions routed through subsidiaries prior to collapse. Intellectual property was carved up among secured creditors, leaving employees and counterparties with limited recovery. What stood out to restructuring professionals was not just the scale of the failure, but the absence of a viable turnaround effort despite months of negotiations and escalating professional fees.
RMIT filed for Chapter 11 in late 2022, citing rising interest rates and liquidity pressure. Over the following year, bankruptcy court records showed repeated disputes over debtor-in-possession financing, administrative claims, and creditor priority. While the estate burned millions of dollars per month in professional fees, resolution was halting. Judges ultimately approved a wind-down prioritizing larger creditors, while smaller disputes lingered long past their economic relevance.
For insurers observing closely, the case highlighted a critical risk: private credit tied to insurance-adjacent assets can quickly become legally and operationally messy, with outcomes driven as much by litigation posture as by economics.
Leadenhall’s profile rose sharply in 2024 with its New York federal lawsuit against 777 Partners and A-CAP, alleging fraud, breach of contract, and improper pledging of collateral. The dispute involves the Premier League Everton Football Club, where 777 was the owner, and Leadenhall alleges 777 violated court orders related to the assets, complicating the football club’s sale.
Courts granted temporary restraining orders freezing assets tied to what Leadenhall claimed was more than $600 million in accelerated debt. Trade publications noted that judges allowed discovery to proceed, signaling the seriousness of the allegations.
Leadenhall didn’t immediately respond to a request for comment from CorpGov.
Regardless of the outcome, the episode underscores a core insurer concern: lending against opaque collateral pools where documentation, control rights and enforcement are existential, not technicalities.
Individually, each episode can be dismissed as bad luck or sector-specific turmoil. Taken together, they reveal a consistent profile: capital deployed into complex, regulated, or opaque insurance-adjacent businesses, followed by delayed course correction and litigation-heavy resolution.
This matters because insurance capital isn’t venture capital. It backs regulated liabilities and public trust. As the Leadenhall saga showcases, when external managers misjudge risk or mishandle distress, the consequences flow directly to insurers, policyholders and regulators.
