Michael J. Pinsel

MICHAEL PINSEL is co-leader of Sidley’s global Insurance practice, and heads the firm’s property and casualty alternative risk transfer practice.

His practice is concentrated primarily in the corporate and regulatory representation of insurance companies, investors and financial advisers with a focus on alternative risk transfer transactions, including insurance securitization and derivatives transactions (catastrophe bonds, sidecars, industry loss warranties); the organization and operation of insurance-linked securities funds; complex reinsurance arrangements; acquisitions, divestitures and corporate reorganizations; the formation, capitalization and corporate financing of insurance companies and related ventures; the regulation of insurance holding company systems; the regulation of insurance company investment practices, including the use of derivative instruments; and the development and funding of insurtech businesses.

Michael’s practice also involves the representation of investment banks, hedge funds, private equity funds, investment advisers, derivative dealers and other sectors of the financial services industry, with respect to their insurance industry relationships and transactions.

From February 1999 until March 2001, Michael served as Senior Vice President and General Counsel of a property/casualty insurance organization operating in both the excess and surplus lines commercial market and the personal lines market. He previously had been a partner in the insurance practice of another law firm.

Michael is recognized by Chambers USA (2008–2025) for Illinois Insurance: Transactional & Regulatory. Clients say “Michael has a very strong command of what is market and what are practical solutions to complex issues”(2025) and that he “is the go-to lawyer for re/insurance and alternative risk transfer corporate transactional advice” (2024). Clients also commend his “deep subject matter knowledge” and “valuable guidance on commercial aspects of transactions” (2023). He has also been recognized by Best Lawyers and was named among BTI Consulting Group’s “M&A Client Service All-Stars” in 2021. In 2023, the firm’s alternative risk transfer practice, in which Michael leads the property and casualty team, was named “Reinsurance Facilitator of the Year” at the Trading Risk Awards for the second consecutive year, and in 2024 the team won Insurance Insider’s “Cyber ILS Award.” He is a frequent speaker on insurance topics, including alternative risk transfer.

Examples of Michael’s recent representations include:

• Ryan Specialty in the launch of its flagship multi-class P&C sidecar that raised approximately US$400 million in committed capital.
• Accelerant in its upsized second Flywheel Re P&C sidecar.
• Vantage in establishing a substantial reinsurance capacity facility funded primarily by third-party capital.
• Ark in the formation of its third-party capital-backed US$250 million Outrigger property catastrophe reinsurance sidecar.
• State Farm in its US$1.2 billion investment in ADT.
• Accelerant in the launch of its US$175 million Flywheel Re sidecar investment vehicle focused on the SME market.
• American International Group in the US$400 million Tailwind Re Series 2022-1 named storm and earthquake catastrophe bond.
• Tokio Marine in its US$200 million Umigame Re Japan typhoon and flood catastrophe bond.
• Private equity-backed Gryphon Mutual in the US$50 million Wrigley Re California earthquake catastrophe bond.
• Tokio Marine in its US$150 million Kizuna Re III Pte. Ltd. Japan earthquake catastrophe bond.
• Integral ILS, a Bermuda-based independent insurance-linked securities fund manager, in its launch.
• Premia Holdings in the formation of its US$265 million legacy sidecar, Elevation Re.
• Allianz in its reentry into the catastrophe bond market in 2020, through the US$175 million Blue Halo Re U.S. storm bond.
• Markel Corporation in its US$919 million acquisition of State National.
• ACE in a venture with BlackRock in connection with the organization and US$800 million private placement of ABR Reinsurance Capital Holdings Ltd., a Bermuda-based reinsurance organization. The venture was named “Capital Raising of the Year” and “Launch of the Year” at the 2015 Reactions North America Awards.
• Japanese insurer Zenkyoren on the transfer of a combined US$3.575 billion of earthquake risk through the Nakama Re series of catastrophe bonds (2014–2023).