1980s
In 1986, driving the No. 23 Kool-Aid car for Bahari Racing, Waltrip finished second in the Cup rookie of the year race to Alan Kulwicki on the strength of a pair of 11th-place finishes at Martinsville and Pocono. The following season, he posted his first career top-ten finish when he ended up tenth in the spring race at Martinsville Speedway. In 1988, Waltrip began running Busch Series events, making five starts for his brother Darrell's team. He took the checkered flag for the first time at Dover in his fourth start. In 1989, he had his first top-five finish in the No. 30 Country Time Lemonade/Kool Aid Pontiac.
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