Waltrip is the younger brother of three-time series champion Darrell. And while that connection certainly hasn't materially harmed his career, it isn't the only reason Waltrip has had a 25-year-career at NASCAR's top level.
Waltrip began racing go-karts around Kentucky in the mid-1970s. But his career took flight in 1981, when he captured the Mini-Modified division track championship at Kentucky Motor Speedway. A year later, Waltrip entered the Goody's Dash Series and in 1983, he won that series' championship. He was also voted that circuit's most popular driver in 1983 and 1984 (perhaps another clue to his career longevity).
Waltrip is one of those drivers who actually made his Cup debut before making his first Nationwide start (in his case, his first Cup start came in 1985; Nationwide waited until 1988). In fact, over the course of 20 seasons, Waltrip has ever only run one full season. But that year, 2004, Waltrip won once and finished a career-best 13th in points. And in 270 career starts, or roughly nine seasons, he has won 11 races and finished in the top five 48 other times. It's a measure of success that Waltrip has never been able to match at the next level.
Waltrip's Cup career has been characterized by futility. Indeed, until he finally won the Daytona 500 in 2001, he held the dubious distinction of running more Cup races (462) without a win than any other driver in series history. Though he would go on to win another race in 2002 and two more in 2003, including another Daytona 500, each of Waltrip's four wins has come in restrictor-plate races. Even more, he's never finished better than 12th in the overall standings, a position he last achieved in 1995.
In 2006, Waltrip announced that he would become an owner/driver in 2007, a surprising decision to say the least. In addition to his stunning lack of success as a driver, recent NASCAR history is littered with drivers, many more successful than Waltrip, who have attempted this difficult double. They failed. Waltrip seems poised to repeat their failures, having qualified for just 14 races in 2007; and while he made each of the 36 races in 2008, he managed one top five and a measly 29th-place finish in points.
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