On May 7, 1972 Darrell made the first of what would end up being over 800 starts in NASCAR's premier division, the Winston Cup Series. Darrell's first Cup car was not pretty; it was a beat up old Mercury sponsored by Terminal Transport, and it carried car No. 95. The car was originally not up to Winston CUp specs; however, DW worked the entire weekend on the car and was able to fix up the car enough to qualify 25th. In the race on Sunday, David Pearson won a thriller by ducking under Bobby Isaac on the white flag lap while he tangled with a lapped car to win. Hardly anyone noticed Waltrip, who did happen to lead under caution before the car's engine blew on lap 69. Nevertheless, young DW had gotten his first taste of Winston Cup, and he entered four more events that year with much better luck; he blew an engine in the second Talladega race (38th) but recorded Top 10s at Charlotte (6th) and Atlanta (8th) towards the end of the season...he also finished a surprising 3rd at his home track, Nashville, albeit 16 laps behind the winner. With only 5 starts, Waltrip was poised to make a run at the rookie title in 1973.
Waltrip started out the year still driving his own Mercury, sponsored by Terminal Transport, and went after Rookie of the Year Honors. He began the year on a high note by making his first Daytona 500, qualifying 11th and finishing 12th, 12 laps behind winner Richard Petty. He went on to post a Top 10 at Rockingham (6th) and was running in the Top 5 at Atlanta when he got involved in a crash ahead of him. The spirited runs caught the attention of others.
"He's the best rookie I've ever seen on a race track," praised race winner Pearson. "He knows what he's doing out there. He's a racer."
In the second Talladega race of that year, there was a tragic accident which claimed the life of 1972 Rookie of the Year Larry Smith. Following the crash, Bobby Isaac, driving Bud Moore's famed No. 15 Ford, suddenly received "a sign from above" that he shouldn't be racing Winston Cup anymore, and just plain pulled off the track on the 90th lap. He would never compete full time in Winston Cup again.
Darrell finished 7th in that race driving the No. 95 car, and after Bud Moore took a one race hiatus at Nashville (where Darrell qualified 3rd only to have mechanical problems), it was announced that Waltrip would replace Isaac in the car for the rest of the 1973 season. It was a great opportunity for Waltrip to showcase his talent, as Bud Moore's team was one of the top rides in the series. However, the pairing was a disaster from the very start, as Darrell hit the wall on the first lap of driving his new ride, in the Southern 500 at Darlington. While Darrell came back after repairs to finish 8th, his best finish in the last 5 races of the season (the 15 team skipped Martinsville) was a dismal 20th. Crashes and mechanical problems doomed the team. The late season collapse allowed rival Lennie Pond to come back and capture the Rookie of the Year Title in his No. 54, and Darrell found himself passed over for the Bud Moore ride the following year in favor of road racing ace George Follmer. TO BE CONTINUED....