2001-2006
Waltrip was hired by Dale Earnhardt to drive his team's new #15 NAPA Auto Parts Chevrolet Monte Carlo entry. In his first race with the team, the 2001 Daytona 500, Waltrip broke a streak of 462 consecutive Cup races without a victory and won his first career points-paying Cup race. His teammate Dale Earnhardt, Jr. finished in second. Unfortunately, the win itself was overshadowed by Dale Earnhardt, Sr.'s death on the last lap. Waltrip was not aware of Earnhardt's death until a half-hour later when celebrating in victory lane when Ken Schrader, whose car had been collected by Earnhardt's car in the same crash, and had been treated and released from the infield care center, informed him that Earnhardt had been taken to Halifax Medical Center, two miles from the speedway, where he had been pronounced dead-on-arrival at 5:15 PM EST.
Waltrip did not have another top-ten finish until returning to Daytona in July, where he finished second while holding off the field as teammate Dale Earnhardt, Jr. won his first plate race (They finished in reverse order of the Daytona 500). Earnhardt, Jr.'s Pepsi 400 finish was emotional to the entire DEI team and when Earnhardt, Jr. did his burnout on the infield grass, Waltrip pulled up alongside him. Waltrip would have a second place finish at Homestead to Bill Elliott, and finished 24th in the standings.
The next season, Waltrip won the second Gatorade Duel. His next top ten finish would be a second place finish at Talladega, where he and Dale Earnhardt, Jr. combined to lead more than two-thirds of the race, with Earnhardt, Jr. taking home his second of four straight wins at Talladega. The following week, Waltrip finished tenth at Auto Club. He had eighth place finishes in the Coca-Cola 600 at Charlotte and the first Pocono race, and fourth place in the first Michigan race. He picked up his second career win at the Pepsi 400 at Daytona. After a ninth place finish at Watkins Glen, and eighth place finishes at New Hampshire and Talladega, Waltrip finished 14th in the points standings.
In 2003 Waltrip won a rain-shortened Daytona 500 and also took victory at the EA Sports 500 at Talladega (his only non-Daytona win), while running in the top-five for most of the season before falling back to 15th in points. Of trivial note, Michael Waltrip won the first three NASCAR on Fox races at Daytona (2001 and 2003 Daytona 500s, and the 2002 Pepsi 400) with Michael's brother Darrell in the broadcast booth. His Talladega win was also his only win at a NASCAR on NBC race.
In 2004, Waltrip went winless and dropped five spots in the standings. Despite one pole and seven top-tens in 2005, Waltrip announced he and sponsor NAPA would depart DEI to drive the No. 55 Dodge Charger for Bill Davis Racing. In 2005 Waltrip only had a few top tens resulting in the top 20 in the final standings. He had an incident with Robby Gordon at New Hampshire. After Waltrip accidentally wrecked Robby Gordon and was spun in retaliation, Gordon furiously wagged his finger and threw his helmet at Waltrip's hood. Waltrip repeated the words Gordon said the previous year in another helmet-tossing incident: "He just threw a helmet on my car." Waltrip was fined $10,000 after he supposedly gestured at Gordon for the damage on his car from the helmet but Teresa and him appealed and the fine was cancelled after a short investigation proved the charge false. Gordon however was fined $50,000 and put on probation for the rest of the year after he was discovered to have said "You know everybody thinks Michael is this good guy...he is not the guy he acts he is and he wrecked me and he is a piece of ****." Waltrip and Gordon after a talk made up and continued their careers. After the former No. 77 Jasper Motorsports team closed its doors at the end of 2005, Waltrip split unofficially from Davis and assumed the former Jasper team's owner's points in order to be guaranteed a spot in the first five races for the season. Running under the banner, Waltrip-Jasper Racing, the team would be used to set up Waltrip's new Toyota operation in 2007. Waltrip failed to qualify for the first time since 1998 at the Coca-Cola 600. He bought a slot from the No. 74 McGlynn Racing Dodge from Derrike Cope to drive in the race and to keep his streak of 262 consecutive races. Waltrip ended up missing three races total in 2006 and did not have a top-ten finish.
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