Waltrip drove for James (Jim) Smith from 1999 to 2000 in the Cup Series. In 2001, Waltrip moved to Dale Earnhardt, Inc. (DEI) to drive the NAPA AUTO PARTS race car. The racing veteran earned a total of four wins during his five seasons at DEI, including Daytona 500 victories in 2001 and 2003. In 2006, Waltrip-Jasper Racing, a new team affiliated with Bill Davis Racing, fielded Waltrip's No. 55 NAPA machine.
In 2007, Waltrip not only competed for the 2007 NSCS championship in the No. 55 NAPA AUTO PARTS Toyota Camry, but also expanded his role as a full-time car owner of MWR that included three Sprint Cup teams and a NASCAR Nationwide Series (NNS) team. Waltrip and his teammates, 1999 NASCAR Cup Series champion Dale Jarrett and rookie David Reutimann, led Toyota's efforts during the manufacturer's first year in NSCS competition. Waltrip also opened the doors of his one-of-a-kind race shop and fan experience, Michael Waltrip Racing.
The 2008 season saw Waltrip qualify his No. 55 NAPA AUTO PARTS Toyota Camry on the front row of the 50th running of the Daytona 500. On Oct. 26 at the Atlanta Motor Speedway, he achieved an impressive milestone when he made his 1,000th NASCAR start. Waltrip, Mark Martin and seven-time NASCAR Cup champion Richard Petty are the only drivers to have accomplished the feat.
His Michael Waltrip Racing organization saw the end of an era when Jarrett retired after running the first five events and the Sprint All-Star Challenge. Reutimann took over the seat of the No. 44 Toyota Camry and earned the team four top-10 and 21 top-25 finishes. Reutimann wrapped up the year by winning his first NSCS pole at Homestead-Miami Speedway. Also in October, MWR announced its technical alliance with JTG-Daugherty Racing and Australian driver Marcos Ambrose in the No. 47 Toyota.
In 2009, Waltrip celebrated his 25th season in NASCAR's premiere division and ninth season with sponsor NAPA AUTO PARTS. In May, in front of a live audience and televised on SPEED, Waltrip announced MWR's sponsorship extension with NAPA, his plans to drive a limited schedule in 2010 and his successor Martin Truex Jr. to drive the No. 56 NAPA AUTO PARTS Toyota. By the end of the season, Waltrip's organization had collected its first NSCS victory with Reutimann's win at the 50th running of the Coca-Cola 600,two poles, five top-five and 12 top-10 finishes in NSCS competition. His Nationwide Series team finished the year with two poles and 10 top-10 finishes. The season also saw MWR boast a 100-percent renewal rate by signing Aaron's, Best Western and Toyota as well as adding a multi-year partnership with TUMS.
The building that bears his name, Michael Waltrip Racing, currently fields two NSCS teams with drivers Martin Truex Jr. and David Reutimann and houses the Diamond-Waltrip NNS team with driver Trevor Bayne and JTG-Daugherty's No. 47 NSCS operation with driver Marcos Ambrose.
In addition to his role as co-owner, Waltrip has been a popular television personality on SPEED since 1996. He's an analyst for its NASCAR Camping World Truck Series broadcasts and was an original member of one of the longest running shows on the cable network, “This Week in NASCAR” 1996-2009.
The 2010 season holds the hope of multiple trips to victory lane for Waltrip as either one of the youngest multi-car owners in NASCAR or as a driver capping a 25-year career.
Or maybe even both.
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