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Ascot, Antares Launch $500M Wayfare Reinsurance Sidecar 

Ascot, Antares Launch $500M Wayfare Reinsurance Sidecar 

Ascot Group Limited and Antares Capital have announced the launch of Wayfare Reinsurance Limited, a Bermuda-based reinsurance sidecar vehicle, in conjunction with Canro Re Limited, a segregated account company also based in Bermuda. The venture will be capitalized with $500 million in equity investments from both Ascot and Antares, marking a strategic step forward in blending reinsurance and private credit expertise to support growth in specialty casualty markets. 

Wayfare Re will provide underwriting capacity to Ascot in support of its U.S. and Bermuda casualty (re)insurance platforms, strengthening the company’s ability to scale in key global markets. In parallel, Antares Capital—a leading middle market direct lender—will serve as Wayfare Re’s exclusive private credit asset manager, deploying capital through its senior secured lending strategy to sponsor-backed U.S. middle market borrowers. 

“The launch of this innovative structure is reflective of an increased appetite from capital markets firms to partner with quality underwriting organizations to drive stakeholder value,” said Jonathan Zaffino, CEO and President of Ascot Group. “It is also a key achievement in the continued buildout of Leadline, increasing Ascot’s capital resilience and enabling us to be a more perfect partner for our clients.” 

For Antares, the initiative signals continued momentum in its growing Insurance Solutions business, which focuses on bespoke partnerships that align private credit with insurance capital needs. “Wayfare Re represents a modern, scalable partnership that combines Antares’ private credit expertise with Ascot’s outstanding casualty underwriting capabilities,” said Ben Concessi, Chief Strategy and Transformation Officer at Antares. 

Aon Securities LLC served as sole structuring agent and placement agent for the transaction. Legal counsel was provided by Willkie Farr & Gallagher LLP and Appleby (Bermuda) Limited on behalf of Ascot, and Debevoise & Plimpton LLP on behalf of Antares. 

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About Joe Palmisano

Joe Palmisano is Editorial Director for Connect Money, where he brings nearly three decades experience of market insights as a financial journalist, analyst and senior portfolio manager for leading financial publications, advisory firms, and hedge funds. In his role as Editorial Director, Joe is responsible for the selection of content and creation of daily business news covering the financial markets, including Alternative Assets, Direct Investment and Financial Advisory services. Before joining Connect Money, Joe was a financial journalist for the Wall Street Journal, regularly publishing feature stories and trend pieces on the foreign exchange, global fixed income and equity markets. Joe parlayed his experience as a financial journalist into roles as a Senior Research Analyst and Portfolio Manager, writing daily and weekly market analysis and managing a FX and US equity portfolio. Joe was also a contributing writer for industry magazines and publications, including SFO Magazine and the CMT Association. Joe earned a B.S.B.A. in Finance from The American University. He holds the Chartered Market Technician (CMT) designation and is a member of the CFA Institute.