In 2008, the Wood Brothers Racing team was at what is perhaps one of the lowest points of its 75-year history.
The team made only 28 starts during the 36-race season that year, with its only top 10 coming from a third-place finish from road course ace Marcos Ambrose. However, even that didn’t really count, as the Australian’s No. 47 entry was funded by Tad Geschickter’s JTG Daugherty Racing outfit. The rest of the time, the No. 21 Ford was acting as a backmarker in entries that featured past NASCAR Cup Series champion Bill Elliott on its roster solely for the sake of using the past champion’s provisional of the time to qualify.
The team’s third driver and heir to the Wood Brothers legacy, Jon Wood, had enough. For the sake of his family’s business, he put down his driver’s helmet and hung up his fire suit for good, ending a racing career that spanned the course of seven years and featured two NASCAR Craftsman Truck Series wins. From then on, Wood took on a managing role at his family’s race team and hasn’t looked back since.
“It was a really, really hard time,” Wood told Frontstretch. “We lost our Air Force sponsorship. I was driving the Air Force races. Bill [Elliott] was driving the Motorcraft races, and it was either have Bill do it and make [the races], or I could share some of the races and miss them. And what’s the point of that? I got to put the team first ahead of my own ambitions and desires.
“And that’s what happened. There was no controversy. Nothing. That’s just what it was. I wasn’t going to do a start-and-park. I wasn’t going to keep chasing a dream or a goal that wasn’t going to materialize. It made more sense to step back and refocus and shift to the team side.”
Since then, for the Wood Brothers Racing team, the rest is history. After creating a partnership with first Roush Racing and later Team Penske, the legacy of the No. 21 has resurged and is closer to the days of its former glory than it ever has been in the last four decades. With four wins since 2008, including a Daytona 500 victory and two in the last 23 races, the legacy of the No. 21 is alive and well.
And for every one of them, 43-year-old Wood has acted as a leader, managing his race team. Now married with two kids, he’s perfectly OK with the decision to leave driving.
“This place will eat you up,” Wood said. “It’s a full-time commitment, and I think it’s tough to juggle family life and NASCAR life. When you’re a driver, you can kind of have the luxury of dragging your family with you. I didn’t have any kids or wife in that point in time, so it was a lot easier.”
As part of the Wood family, the current day president of Wood Brothers Racing knew how tough it was to not see his father Eddie Wood for long periods of time — something he’s trying his best not to replicate.
“My dad was not around a lot when I was at the age my kids are now,” Wood said. “It was a different NASCAR back then. You’d leave on Wednesday, and you were back on Sunday night, and it was every single week. When you weren’t at the racetrack for a race, you were testing.
“So, it was a full-year, never-ending thing. It’s not that I resent that. It’s not that I hold any grudges. He did what he had to do. There are no ill feelings. I just want to be there with my kids, because I’m starting to see what everybody’s told me: how fast it goes. One minute, they’re in diapers. The next minute, they’re driving. It’s more rewarding when I’m there on Saturdays on the baseball field than if I’m here at the racetrack.”
The day before this interview, Wood was spending his day coaching his kids’ baseball teams, something he’s been doing on the Saturdays before traveling out to the Cup races on Sunday mornings.
And he’s good at it too. They’ve gone undefeated this year.
“I’m serious about it,” Wood said with a smile. “It’s the real deal. … The oldest [kid] is in a travel team. There are tournaments on Saturdays and Sundays. I miss some of the ones on Sundays. Sometimes I try to skip the races for baseball. I prioritize baseball. I’m not scared to admit that.”
Wood taking time away from the race team certainly hasn’t hindered its performance recently either. He’s still been able to share in its recent success even when he’s not at the track.
He operates as the team’s social media handler — a position that is usually entirely done by teams’ public relations personnel, and one that he did not want to have at all when he first started.
“I didn’t want to do it.” Wood confessed. “My sister went to a wedding. She did [social admin], and I didn’t even have a Twitter [now X] account. It was [Talladega Superspeedway] in 2012. I just felt like social media’s supposed to be a place to pass along ideas, not be sponsor-perfect. That was my opinion. It was easier just to tell the truth from the beginning.
“‘We sucked this weekend.’ End of story. ‘Keep your expectations low.’ Tell it how it is.”
the struggle bus just stopped and picked us up, for this run at least. not real sure what happened but we went from solid to soiled. we'll see how it goes but not fun rn
— Wood Brothers Racing (@woodbrothers21) March 23, 2025
Of course, you might expect that mindset has gotten him into trouble.
And you’d be right.
“It’s gotten me in trouble a lot,” Wood admitted. “I remember a lot of uncomfortable discussions with some of NASCAR upper management in my earlier days of doing it. I had to learn the hard way in how far you can take it.
“I don’t even remember what I said. It wasn’t deliberate. It was just pushing the boundaries of what’s acceptable.”
Through his time as a social media admin and team president, Wood has seen plenty of critical moments of the Wood Brothers Racing milestones in the last decade.
But perhaps the oddest for him, however, was Harrison Burton‘s win at Daytona International Speedway last August.
While searching for its 100th victory, the team hired second-generation racer Burton to pilot the famous No. 21 in 2022. The result was three straight years of the organization’s worst results since 2015.
In mid-2024, WBR told Burton he would not return to race for the team in 2025. Ironically, only a few weeks later, Burton drove the famous Ford entry to victory lane at Daytona, a track that has been good to the Wood family over the years.
It was the storied team’s long-awaited 100th win in its 74-year existence. Yet while everyone on the No. 21 crew exploded in celebration on pit road, Wood could only sit there on top of the pit box, puzzled at what to do. He turned toward Team Manager Jefferson Hodges.
“Is this how I’m supposed to feel?” the conflicted Wood said to Hodges. “Am I supposed to feel weird about this? Am I supposed to be struggling with this?”
The feeling was bittersweet for Wood. If the surprise victory had happened two months earlier, Burton’s career path would look much different than it does now. While he was happy for the young racer, he still wasn’t sure how to feel.
“It was a weird feeling,” Wood said. “When you see the car cross the finish line and they’ve won the race, for me anyway, it was like, ‘How am I supposed to feel?’ Because for years, people have played this 100th win up like it’s just monumental.
“Then it happens, and it’s like, ‘How’s this supposed to go?’ I wasn’t expecting it. I think I was expecting it to be more of a probability now than it did last year. I was a little bit conflicted.”
But a win did happen again this year. At Las Vegas Motor Speedway in March, the team’s current driver Josh Berry also won his first career Cup Series race and the second for WBR in 17 races — the shortest span of events between Wood Brothers wins since Neil Bonnett‘s win at Charlotte Motor Speedway in 1982.
It was no fluke either. In 2025, Berry has gone on to earn three top 10s and two top fives. That’s already more than every full season since 2021.
“The last couple of years were frustrating,” Wood said. “This year has been a lot more fun. The end of last year was a lot of fun, but that changes the calculus. Waking up on Sundays and knowing you’re going to be competitive, that makes the flight here a lot faster.
“It’s just a better attitude.”
During Berry’s post-race press conference, Wood brought out his phone and posted on X with his clearly happier demeanor. A father of two, coach of an undefeated baseball team and team owner for a playoff-bound Cup organization for the second straight year, he has every reason to have one.
Sorry for the lack of posts and stuff. We joke about the admin stuff but we legit don’t have admin. I’m sitting beside josh in the media center typing this. And @bobpockrass won’t look up but it’s because he knows he f-ed up and didn’t pick us as longshot but we’ll let that slide pic.twitter.com/OgeXQ4UeKb
— Wood Brothers Racing (@woodbrothers21) March 17, 2025
Dalton Hopkins began writing for Frontstretch in April 2021. Currently, he is the lead writer for the weekly Thinkin' Out Loud column, co-host of the Frontstretch Happy Hour podcast, and one of our lead reporters. Beforehand, he wrote for IMSA shortly after graduating from Embry-Riddle Aeronautical University in 2019. Simultaneously, he also serves as a Captain in the US Army.
Follow Dalton on Twitter @PitLaneCPT