High Quality Content by WIKIPEDIA articles! Michael Curtis Waltrip (born April 30, 1963) is a semi-former professional race car driver, co-owner of Michael Waltrip Racing, and a published author. He is the younger brother of three-time NASCAR champion and racing commentator Darrell Waltrip. Waltrip is a two-time winner of the Daytona 500; having won the race in 2001 and 2003. He is also a commentator for SPEED TV`s coverage of the Camping World Truck Series and is an analyst on the Showtime series Inside NASCAR, along with Chris Myers, Brad Daugherty, and Randy Pemberton.