002 RedBird Capital’s Bishop Street Underwriters with Jim Arnold and George Wilson

RedBird Capital owns AC Milan, a Formula One team, and — through Fenway — Liverpool FC and the Boston Red Sox. It also owns a sports insurance business that doesn’t cover any of this.

Bishop Street Underwriters has been buying into American amateur sport since 2023: nine operating companies now, $650m of premium last year, $800m targeted this year. Jim Arnold and George Wilson run its sports and entertainment division. On why you buy two competitors and use each to fix the other’s weakness, what a founder-friendly sponsor does differently with a family business, and why flag football is now one of the more interesting underwriting problems in the market.