Michael Waltrip began his career as a car owner in 1996, driving a No. 12 Ford Thunderbird in the Busch Series. The operation gradually expanded, fielding cars across multiple numbers and accumulating wins at tracks including Michigan International Speedway and Bristol Motor Speedway during Waltrip's time as an owner-driver. The team made a brief foray into the Winston Cup in 2002 with the No. 98 Aaron's Chevrolet driven by Kenny Wallace but sold those owner points after a single race.
MWR's full-time Cup arrival coincided with Toyota's entry into the series, with Waltrip constructing a three-car operation alongside partner Robert Kauffman. The 2007 season opened in disaster when MWR's entries were disqualified from their starting positions in the Daytona 500 due to an illegal fuel additive found in Waltrip's No. 55 car during qualifying. The team members received fines of $100,000 each and multiple suspensions. Though they requalified using backup cars, the organization struggled throughout the year, failing to qualify for numerous races and losing sponsors including Burger King and Domino's Pizza.
Dale Jarrett, who transferred his UPS sponsorship from Robert Yates Racing to drive MWR's No. 44, suffered similarly, failing to qualify for twelve races across the season and scoring no top-10 finishes in what became his farewell season before retiring from points racing in 2008.
The 2009 season marked MWR's competitive turning point. David Reutimann won a rain-shortened Coca-Cola 600 on May 25, 2009, giving the team its first Sprint Cup victory after years of struggle. Martin Truex Jr. joined as a full-time driver in 2010, expanding the competitive core. By 2012, MWR reached its peak as a three-car operation with Clint Bowyer in the No. 15, Truex in the No. 56, and the No. 55 shared between Mark Martin and Brian Vickers. Bowyer won three races in 2012 — at Sonoma, Richmond, and Charlotte — and finished second in the points standings, the highest championship finish for any MWR driver.
The most consequential moment in MWR's history occurred at the Federated Auto Parts 400 at Richmond in September 2013. Clint Bowyer spun his car with seven laps remaining under circumstances that triggered a NASCAR investigation. The inquiry found that general manager Ty Norris had ordered Brian Vickers to pit under the ensuing caution specifically to manipulate the finishing order and assist Martin Truex Jr. in securing the final Chase wildcard spot ahead of Ryan Newman. NASCAR issued what were then among the stiffest penalties in its history: a $300,000 team fine and a 50-point deduction applied to all three MWR cars, which had the direct effect of ejecting Truex from the Chase and inserting Newman. Norris received an indefinite suspension; crew chiefs received probation. NAPA Auto Parts subsequently ended its long-running sponsorship relationship with MWR, which forced Waltrip to release Truex from his contract.
Without Truex and NAPA, MWR contracted to a two-car structure for 2014 and 2015, fielding Bowyer in the No. 15 and the No. 55 primarily for Brian Vickers, whose recurring blood clot issues kept him sidelined for extended periods with David Ragan and Brett Moffitt substituting. On August 19, 2015, co-owner Rob Kauffman announced that MWR would cease full-time racing after the season concluded. Most MWR equipment and several employees transitioned to BK Racing for 2016, while the team's two Cup charters were sold to Stewart-Haas Racing and Joe Gibbs Racing, where they currently operate as the No. 41 and No. 19.
MWR maintained several technical alliances throughout its existence, including arrangements with JTG Daugherty Racing, Germain Racing, Prism Motorsports, and AF Corse in sports car racing. The team also recruited experienced Formula One personnel, including former McLaren head of race operations Steve Hallam, reflecting Waltrip's ambition to professionalize the organization beyond typical NASCAR standards.
Michael Waltrip Racing produced seven Sprint Cup Series victories across its operational life and demonstrated that Toyota could win at NASCAR's highest level within two seasons of entering the series. The 2013 Richmond affair stands as one of the more explicit documented cases of team manipulation in NASCAR's modern era and contributed to subsequent rule changes around playoff manipulation. The team's No. 15 and No. 55 charters live on within Joe Gibbs Racing and Stewart-Haas Racing's current operations.