Michael Waltrip hold’s NASCAR’s least sought after award of the most Winston Cup starts without a win (463) but that hasn’t meant he hasn’t been a competitive driver on the track. Michael Waltrip, younger brother of Darrell Waltrip, three time Winston Cup Champion, has had his share of success.
Michael started racing in his teen years running mini-modifieds in Kentucky. In 1981 he won the track championship at Kentucky Motorspeedway. In 1982 he entered the Goody’s Dash Series and by 1983 he had won the Championship as well as the series most popular driver award. In 1984 he was once again named the series Most Popular Driver.
Michael Waltrip ran five Winston Cup races in 1985 and ran his first full schedule in 1986. With 16 top-20 finishes he was runner up to Alan Kulwicki for Rookie of the Year. In 1988, Michael ran five races for brother Darrell’s BGN team and took the checkered flag on his fourth start. At Bristol in 1993, Waltrip won the BGN race and made the first “Polish Victory Lap” in honor of friend Alan Kulwicki who had died that weekend getting to the event.
Although Michael Waltrip remained competitive in the Winston Cup series he could never quite make it to victory lane. That changed in September of 2000 when friend Dale Earnhardt asked Michael to join Dale Earnhardt Inc.
In February of 2001 Michael Waltrip won the Daytona 500 with teammate Dale Earnhardt Jr. coming in second. Unfortunately for Waltrip, and for the whole racing community, Dale Earnhardt died instantly in a crash on the last lap of the Daytona 500. Waltrip went on to take a second place finish behind Dale Jr. later in the season at the Pepsi 400 also in Daytona. He had one more second place finish and ended the season in the 24th place overall.
Waltrip had a second place finish behind Dale Jr. at the Aaron’s 400 at Talladega in 2002 and another Pepsi 400 win. In 2003, Waltrip once again took the checkered flag at the Daytona 500. He also won the EA Sports 500 at Talladega with Dale Jr. taking the second place finish. With 2 victories and 9 additional top-ten finishes, Waltrip ended the 2003 season in 15th place.