How the 1996 All-Star Race Etched Michael Waltrip, Wood Brothers Into History

As the NASCAR Cup Series gears up for the annual All-Star Race at North Wilkesboro Speedway on Sunday (May 18), Wood Brothers Racing’s latest revelation is turning back the clock to 1996.

A team known to pull off major upsets at points in its historic timeline, the 1996 All-Star Race was a prime example, when Michael Waltrip guided the illustrious No. 21 to victory lane.

Now, that triumph will be celebrated in the form of Josh Berry‘s No. 21 Ford Mustang, nearly three decades after Waltrip earned his lone All-Star victory at Charlotte Motor Speedway; which hosted the All-Star race from 1985 to 2019.

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— Wood Brothers Racing (@woodbrothers21) May 13, 2025

Waltrip’s victory was not only a stunner throughout the garage or another notch in the Wood Brothers’ legacy; it was also a pivotal moment for both sides.

At the time, the younger brother of three-time Cup champion Darrell Waltrip had an undesirable streak of his own. Entering 1996, Michael had been at stock car’s premier level for a decade, recording 309 starts by the time the series headed to Charlotte for what was then called The Winston.

Little to nothing had gone right for Waltrip, who was winless with just a handful of top fives — 16 to be exact. He had come close to victory lane, specifically in the 1991 TranSouth 500 at Darlington Raceway, where he led 208 laps before ultimately finishing third.

Waltrip had spent his entire Cup career with Bahari Racing, primarily in their bright yellow No. 30, up until 1996. Despite recording career-best points finishes of 12th in both 1994 and 1995, equipment drawbacks, incidents and, at times, pure rotten luck, led to Waltrip’s release after the 1995 season.

At a crossroads in his career, Waltrip found the Wood Brothers, a place and time that he still holds dear to his heart.

“I spent the off-season in ’95 and ’96 a lot in Stuart, Va. (where WBR is located),” Waltrip told Frontstretch. “I would visit the team and get to know everyone, and part of the beauty of those memories is sharing stories with Glen and Leonard [Wood] to them telling me about racing […] in the 45 years prior to that, and some of the innovative things that Glen and Leonard had built into race cars, and just the history. It was a really great time for me.”

That great time quickly reflected itself in Waltrip’s performance, as he recorded four top 10s through 10 events into the new partnership. However, still winless, Waltrip had not qualified for the main event of the All-Star Race, needing to race his way in by virtue of the All-Star Open.

Initially, that task seemed to be too grand of an order, as Waltrips recalls.

“Danny Glad had built the engine, and he said he built a special engine — it might make it all night long, or it might not,” Waltrip said. “We were struggling in The Winston Open, and we just didn’t have a good handle on the track. I felt like, in practice on Friday, we were pretty solid, but when the race started to try to make it into the All-Star Race, I battled as hard as I could.”

“Luckily, for me that night, they took the top five finishers to fill out the field for The Winston that night and I finished fifth. That wasn’t easy either. I was in a pretty big battle with, I believe it was Johnny Benson for that fifth spot, but we were able to hang on and make our way into the big show that night.”

One challenge down, one more to go, but given his ill-handling car in The Open, Waltrip practically told Eddie and Len Wood to throw the kitchen sink at it for adjustments. In true Wood Brothers fashion, their craftiness shone through under the bright lights, and it didn’t take long for their driver to notice the improvement.

“[The car] was handling great and doing everything I asked it to do,” Waltrip said of the handling changes in the All-Star Race. “I started last, obviously, in the All-Star Race after barely getting in, and I was passing cars. I would pass one car, then pass the next, and Eddie came on the mic and said, ‘You know, Mike, they’re going to invert the field. If they get passed, you’re going to have to pass them again.’ In my mind, I needed to see how far I could push the car, I needed to see how it would do if I drove it as hard as I could.”

Keeping that field inversion in mind, Waltrip aimed to finish the first segment in 10th in order to restart in that same position when the next segment commenced. That’s exactly what he did, a key ingredient to producing a successful night.

Waltrip’s climb to the front continued in the second segment, as he went from 10th to fourth, arousing curiosity from both the fans and garage that he may truly have a say in the outcome. A 10-lap shootout set the stage for what would become a magical night for Waltrip and company.

“We went into turn 1, and I was fourth, on the outside,” Waltrip recalled. “I was able to clear Rusty Wallace on the outside down into turn 1, and that was a big move for me to get ahead of Rusty and get behind Dale [Earnhardt] and Terry [Labonte]. Terry was leading, I think, and Dale was second. Dale got on the bottom of Terry and got a little bit loose in [turns] 1 and 2, slid up into Terry a bit, and I was able to pass those two champions, three of them really, and drove off to win that night. Obviously, a huge night in my career, and a big night for the Wood Brothers.”

A breakthrough it truly was for the 33-year-old, whose confidence increased lap by lap. Imagine racing into a spot to win, exhibition or not, having to do so by fending off a seven-time champion, as well as two additional stars in their prime. Yet, as unnerving at it may have seemed, a unique perspective carried by Waltrip further fueled his motivation.

“I was kind of well-known for not being able to win a Cup race for a long time, but I had beaten all of those guys before — I just didn’t beat them all on the same day,” Waltrip said. “I knew I was good enough to win. I had won in the Xfinity Series, I had finished second in Cup, I had a lot of top fives, I had poles, so I wasn’t lacking for confidence, but, man, what a relief it was to pull off that win.”

It would be another five years before Waltrip finally got a taste of his first regular-season and points-paying win, albeit in the ill-fated 2001 Daytona 500 that claimed the life of his close friend Earnhardt.

Had Earnhardt not perished that day, it would have been poetic harmony for the results of that race. Earnhardt had hand-picked Waltrip for the No. 15 at his own team, Dale Earnhardt Inc., seeing the raw talent submerged beneath Waltrip’s surface. However, that wasn’t the only ride that Waltrip thanked “The Intimidator” for.

The other? It just so happened to be at the Wood Brothers, though the validity of it is still somewhat of a mystery to Waltrip.

“I don’t know for sure, but I think Dale Earnhardt told Eddie and Len, ‘Michael can win in y’all’s car, you need to get him to drive your car,'” Waltrip said. “I remember not knowing that at the time, but as time went on I think he had a role in that. The gratitude that I have that [the Wood Brothers] gave me that opportunity, I drove for that team for three years, and that was our only win. But we had some great runs, and we were competitive year in and year out. I think when I left there, they were in a better place than they were when I got there.”

Though the relationship on the track only lasted three years, the respect and gratitude between the two sides today is as clear as crystal. And for Michael, being a part of the team’s 75 seasons was an honor that he will ever be grateful for.

“I looked at driving that No. 21 Citgo Ford as the Wood Brothers saying, ‘Okay Mike, we trust you with our car, you go race it the best you can,” Waltrip said. “Winning that night at Charlotte, to be able to get a victory and go to victory lane and celebrate with the family was just really special.”

Nearly 30 years after that first All-Star win for the storied organization, and 75 years into the team’s history, Waltrip has witnessed the peaks and valleys of the team as an aspiring driver, competitor, fellow team owner, television broadcaster, and most of all, a friend. So how has this team sustained itself and remained competitive to its core for over seven decades? Waltrip’s perspective is highly esteemed.

“When I left [WBR], and today, we are just as close of friends as we ever were,” Waltrip said. “Racing is a tight-knit community, and you want to make sure you respect Hall-of-Famers like the Wood Brothers are.

“It’s the evolution of the sport, and they started at the beginning. To be able to see Glen and Leonard hand it off to Eddie and Len, and those guys to be able to keep their finger on the pulse of the sport, I light up when I walk into the garage and they’re standing there. I feel the same way about Richard Petty. You see him at the race track, and you feel like, ‘Yes!’

“This is our heritage, this is our history, and its present. Go up to Len, go up to Eddie and ask them questions of what they saw, and it just makes your heart happy that this is the path that I’ve gone down in my life. I’ve been in that garage area since I was old enough to get in it, and still there today. It makes you really appreciate people like that.”

As for sustaining that success another 75 years, Waltrip said the secret sauce is to do what the team has done 101 times: just keep on winning. And with the relationships and connections the team has established, those will be reachable goals for years to come.

Of course, it was because of a particular night in 1996 that the Wood Brothers technically have 102 wins. But that’s discourse to be debated at another time.