Indianapolis Monthly Magazine - Indianapolis Restaurants, Shopping, Concerts, Events and more. Class Photo: Legends of the Indy 500 - Dan Wheldon Starts: 9 Wins: 2 (2005, 2011) Claim to fame: In May 2011 the British driver established himself as one of the 500’s all-time greats with his second win. He was killed in a crash at Las Vegas Motor Speedway on October 16, 2011.