Michael Waltrip

Michael Waltrip won the 2001 Daytona 500 in the most bittersweet victory in NASCAR history, crossing the finish line in the No. 15 DEI Chevrolet seconds after team owner Dale Earnhardt was killed in a last-lap crash behind him. That moment -- triumph and tragedy intertwined in the most devastating way imaginable -- defined a career that spanned 462 Cup starts and produced four victories. The Owensboro, Kentucky native was the younger brother of three-time champion Darrell Waltrip, and for years he competed without a Cup victory, going winless for 462 starts before that fateful February afternoon at Daytona. The wait made the victory all the more powerful, and the tragedy that accompanied it made the moment eternally complex. Waltrip won a second Daytona 500 in 2003, proving that his superspeedway prowess was genuine and not a one-race anomaly. His four career wins all came at restrictor-plate tracks, where his ability to draft, position, and make the right move at the right time was among the best in the field. As a team owner with Michael Waltrip Racing, Waltrip built a multi-car Cup operation and provided opportunities for drivers including Clint Bowyer, Martin Truex Jr., and Denny Hamlin. His broadcasting career and his infectious personality have kept him connected to the sport and its fans for decades. Michael Waltrip's legacy is inseparable from that February day in 2001 -- a victory that cost more than any driver should ever have to pay.

Written by Richard R. Glover, NASCAR Reference