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Painful Moments in Sports

JR Hildebrand
Photo: Paul Sancya/AP

JR Hildebrand

2011 Indy 500

JR Hildebrand was one turn away from winning the Indianapolis 500 and within sight of the checkered flag when the 23-year-old rookie made the ultimate mistake. On the 800th and final turn of the race, Hildebrand crashed into the wall, allowing Dan Wheldon to cruise to the finish line for his second career victory at Indy and leaving Hildebrand in a gut-wrenching second place.

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