JR Hildebrand lost $1.5 million in the last mile of the Indianapolis 500. He was leading the race heading into the final turn on the final lap when he went high to pass a slower car and slammed into the safety wall, allowing Dan Wheldon to win the 100-year anniversary race.

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Source: http://www.topix.com/nascar/2011/05/wheldon-takes-home-2-6-million-for-indy-500-victory?fromrss=1