It's been a long and winding road for this veteran.
The younger brother of a NASCAR legend, Michael Waltrip began his own Cup career full time in 1986, driving the Hawaiian Punch, Chuck Rider owned Pontiac.
It would be a struggle for the younger Waltrip, finishing years with nearly ten DNFs, and not yet clinching a win. In driver lineups he was often referred to as "Mike Waltrip" or, simply, "Darrell's little brother."
Driving Bahari Racing's No. 30 Pennzoil Pontiac, Darrell's little brother won the Winston Open- his first win, albeit a non-points event. The ride, however, only lasted four more years, when he replaced by Johnny Benson after the 1995 season.
A stint with the legendary Wood Brothers proved fruitless, finishing his three year tenure collecting no poles, no wins, twenty two top tens and only one top five. Waltrip also had a DNQ and ten DNFs.
For Waltrip, it would take thirteen sponsor changes, thirty four DNFs, four car makes, and five car owners to get the 38-year-old his first win- the 2001 Daytona 500.
Dale Earnhardt, Inc. had just hired Waltrip to drive the No. 15 NAPA Auto Parts Chevrolet. It was his first start for the "Intimidator's" team.
As an added bonus, his big brother Darrell called his little brother winning the historic event, Waltrip's 463rd career start.
But that day was historic for tragic reasons as well. Running behind his car- the other, of course, being the No. 8 Budweiser Chevrolet driven by son Dale Earndhart, Jr.- Earnhardt and the the No. 40 of Sterling Marlin made contact, sending the black No. 3 and the No. 36 of Ken Schrader into the wall.
Rightly, Mikey celebrated his first win. His brother talked, as the camera rose above Victory Lane, about praying for Dale.
Earnhardt was finally removed from the car, and driven by ambulance to a nearby hospital.
"I don't like that," the older Waltrip said. "That's the kind of wreck that'll hurt ya."
"I don't really know- I got the heck out of the way," Schrader said when asked about Earnhardt's situation. "I'm just worried about Dale."
The irony of Daytona, Mike Joy called it.
Dale Earnhardt died that day- a defining moment in Waltrip's career.
"My heart is hurting right now. I would rather be any place right this moment than here. It's so painful." Waltrip would say in his press conference later that evening.
The rest of his season wasn't much success, and ended with him finishing 24th in the point standings.
His only other career win also came in a Dale Earnhardt owned car, at the next season's Pepsi 400... at Daytona.
Since leaving DEI in 2005, Waltrip has formed Michael Waltrip Racing, one of NASCAR's first Toyota teams. First as a partnership with Bill Davis, he runs a two car operation for himself and driver David Reutimann, and once had former Cup Champion Dale Jarrett at the wheel.
The team, much like the first 462 races of the owner's career, has been winless, and with little success to boot. Going into 2009, Reutimann's car is sponsorless, due not only to a poor economy, but poor results by a struggling team.
At a Preseason event down in Daytona, Waltrip announced that '09 may be his last year in NASCAR.
"My goal is to go win some races this year, run up front so that I don't have to say this is my last year. But if I don't do those things, if I can't compete at the level that Ruderman does or NAPA expects, then I probably won't get to do this again in 2010." Waltrip said during the Fan Fest.
It looks like this coming season is truly a make or break deal for "Mikey".
Thanks to Racing Reference, NASCAR, Turner Sports and the USA Today for the quotes and stats used in this piece.