Jimmy Spithill, Skipper, Team Oracle USA

A two-time winner of the America’s Cup, in 2013 Jimmy Spithill led his team to what has been called the greatest comeback in international sport.  A multiple world champion in both fleet and match racing, Spithill is both the youngest helmsman to compete for the America’s Cup at just 19, as well as the youngest skipper to claim sailing’s ultimate prize, aged 30. 

During the planning of the ILS Convergence event, Whitfield took advantage of the world champion's relocation to Bermuda and approached him as a keynote speaker for the event. Jimmy Spithill regaled the guests with tales from the world of America’s Cup sailing and shared important lessons in catastrophe management, risk and leadership learned through his experiences.

Jimmy Spithill, a true sporting philanthropist, requested that instead of payment,  ILS Bermuda made a contribution to the “America's Cup Endeavour” youth sailing program in Bermuda.  His keynote not only influenced Bermuda's world leaders in the ILS and reinsurance markets, but also contributed to local community programmes for the island's young people.


“Rarely have I seen a situation where doing less than the other guy is a good thing.”

—Jimmy Spithill, Skipper, Team Oracle

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