Family Values: Jon Wood’s Journey Through NASCAR

Jon Wood is a man that fits incredibly well into the front office of a NASCAR Cup Series operation. With “Senior Vice President” printed on the front of his business card these days, the 40-year-old Virginia native looks and sounds the part of stock car racing’s blended corporate-casual environment. Whether it’s on Twitter, at the track, or in the administrative wing, Jon Wood is a respected delightfully atypical personality in the NASCAR community. As a grandson in one of American stock car racing’s royal families, Jon’s career in the sport might have been expected, but maybe not in the path it actually took. For whom was once a shaggy haired cool kid that contributed to the new age young gun mentality of the 2000s in NASCAR, Jon Wood has gradually gelled into the crisp energetic businessperson that’s keeping one of the sport’s oldest teams thriving in its seventh decade.

To properly understand Jon Wood’s story, it’s important to look both at the present day and how it may have been shaped by his past.


“It’s been challenging” says Jon Wood on the early 2022 Cup season for the famous Wood Brothers 21 car. “It’s not even anyone’s fault, but when you’re buried this deep in points, it really sets a tone and it’s a struggle to get out from.”

Rookie Cup driver Harrison Burton has shown the ability to run well at several times in the first handful of races, but has been involved in multiple accidents in the young season. No better moment illustrates this struggle than their crash at the Daytona 500, flipping the car while running up front. As of today, Harrison Burton sits 32nd in driver points, and 3rd in the rookie standings behind Daytona winner Austin Cindric and Todd Gilliland.

Over the 20 plus years of Jon Wood’s NASCAR experience however, challenge and struggle have been bountiful commodities.


“If you make to this level as a driver, you can make a fast car drive fast. But not everyone gets a fast car all the time.”

Jon Wood rose from the ranks of late models and the Winston West series around the turn of the century, and began racing in the truck series primarily for Jack Roush. The 2001 and 2002 seasons were mostly a struggle with Wood not only in the shadow of his famous surname but following the progression of budding superstars Kurt Busch and Greg Biffle, who had advanced within the Roush organization. Situations like these can cause a driver to question their ability, and in Wood’s case, he seemed to be wondering if he was in the right profession. But when Cup standout Jeff Burton needed a substitute for a Busch (now Xfinity) series race at IRP piloting the Gain sponsored number 9, Wood was able to show his skill in a properly competitive car. “We started 6th and finished 6th, and stayed up front all race…and that was after finishing 8th in the truck race the night before, you’re not supposed to do that! You typically expect to do something stupid and crash in your first Busch race, so that felt really good.” A strong performance in a higher division gave Jon Wood that extra boost of confidence, and perhaps saved his racing career early on, allowing him the opportunity to finally excel.


“Harrison [Burton] doesn’t need my advice for driving, the kid is the son of a super super extra very good driver, and any points he may need he can be like, ‘Hey Dad.’ But the things I have talked to him about are like, ‘don’t pin this stuff on yourself.’ You can’t take the first four races and our lack of speed as something personal on you…he just needs time for the pieces to line up.”

Jon Wood makes precise observations to note Harrison Burton’s success at the Xfinity level, and how he’s careful and mature both in and out of the car. With a rookie Cup driver, new Cup crew chief and a brand new generation of stock car, the balance of the unknown with competitive expectation appears to be the family operation’s highest priority. Even if someone had never heard of Jon Wood before hearing this conversation, the tone of experience resonates throughout. Managing expectations, coming through whenever opportunity arises, and achieving success after the fact are other facets that Wood can evoke from his driving career.


“Now, we finally started running up front.”

Back in the Roush Racing truck for the 2003 season with a newly relocated shop and a fresh batch of confidence, Jon Wood was able to show his ability as a racer with equipment that was expected and was able to win. Teamed with Carl Edwards at Roush, the 50 and 99 trucks were considered the favorites on a weekly basis. Despite some sponsorship trouble, they were still able to notch victories. Jon Wood’s first national touring NASCAR victory came at Kansas in 2003, finishing ahead of Edwards for a Roush 1-2, helping to usher in an era of dominance for the team at all three national levels. While Jon Wood won a 2nd race that same year at his home track of Martinsville, collected twenty Top 10s and finished 5th in points, sponsorship trouble dogged the team at points throughout the season.

A fun fact of Jon Wood’s driving career is that he’s one of the only drivers in NASCAR history to win a race with a political sponsor. Bob Graham (then a presidential candidate), sponsored the 50 truck for 13 races in 2003, the first being the win at Kansas. “Back then, I didn’t know a democrat from a republican, I just wanted to race. The only news to me was that it was a sponsor to pay the bills, and looking back on it I dare say [candidate Graham] didn’t even know he had a truck.” From an era where political sponsors were at best acknowledged and not particularly analyzed, Wood makes a note about the changing climate as the 21st century presses on. “I think some of these deals, the more we see, opens the driver or team up to some pretty nasty things.”


“No matter what happens, you have to own it.”

Racers are all businesspersons in their way, but Jon Wood’s career expresses that notion more literally in 2022. The Wood Brothers organization is one of the best at keeping partners and sponsors in the image of their team, and historically has some of the best relationships in NASCAR. These relationships with businesses and the public aren’t won overnight, and Wood’s experience from both sides paints a unique picture. When asked about the current uneasy climate of political sponsors in NASCAR, Wood is careful to note that it’s a hard line to draw. “I can see arguments from all sides of the spectrum, but I can honestly say that if you as a team or a driver don’t handle things just PERFECTLY, you can end up stuck with a lot of problems just from a politically charged sponsor. You have to believe in what you’re saying. If you’re sponsored by a tampon company, maybe you don’t have to be as passionate about their cause, but something like politics on your car, you better be passionate about it because you’re gonna be tagged with it. You have to own it, when you put it out there like that you’ve made your bed, and you gotta sleep in it, and I don’t know if that’s the best fit for everyone in NASCAR.” Fitting in and making it long term as a driver at NASCAR’s highest levels is challenging enough, as Jon Wood learned in the 2000’s.


“With the schedule the way it is, you don’t have time to react. Next week’s preparation was already done a month ago so if you’re slow, it don’t get better.”

After showing success in the truck series, coupled with promising performances in the Busch series, Jon Wood was presented with the opportunity to compete at the Cup level for his family team. Wood raced one of the most famous cars in racing history for the first time at Las Vegas in 2007, with plans to split time with veteran driver Ken Schrader that season to ease into the Cup ranks. Unfortunately, this was also a time of great struggle for the Wood Bros Cup program, compiled with economic woes that would challenge the sport of racing entirely. “The way Cup racing goes down, when you don’t have speed, it’s really hard to dig out of that rut.” Faced with an uphill battle and the points at the time only guaranteeing the Top 35 in owner standings a start in the race, the Wood Bros were faced with the unusual prospect of missing races. “I hate to really say this, but it was kind of comforting to see Schrader missing races too. I hated it for us, but at least they were having the same problems I’m having.”

The 2008 season under more ideal circumstances would have likely seen Jon Wood in a more robust Cup schedule, but given the team’s distress, Jon made a sacrifice for the good of the family team. “It was my suggestion to use Bill Elliott. I came up with the idea to use Bill for my races simply because he had the past champion provisional. When looking at it, what’s better here: we miss the race, I get to be selfish as the one that drove it? Or do we make the race and hopefully keep this team going?” Decisions for the good of the team are a strong part of the Wood Bros’ culture.


Matt DiBenedetto stands next to his car NASCAR Clash auto race at Daytona International Speedway, Tuesday, Feb. 9, 2021, in Daytona Beach, Fla. (AP Photo/John Raoux)

“I really do think a lot of Matt, but there’s more to this business than liking a guy.”

For the Wood Bros’ Cup operation, the 2nd half of the 2021 season could best be described as “rocky.” Veteran driver Matt DiBenedetto was in the final year of his contract, with the plan to bring Penske top prospect Austin Cindric to the 21 car in 2022. After a classic silly season shuffle involving Brad Keselowski and the Roush Fenway organization, there was some confusion about who might get the seat for the 21 after all, eventually leading to the announcement of Harrison Burton taking the seat for the following year and leaving DiBenedetto out of Cup ride. “It was something that was constantly on my mind,” says Jon Wood. “It was maybe awkward the first two weeks after the announcement, but [Matt] put on a happy face about it and I really don’t know if I could have done that if I was him.”

With the transition of the driver and new generation of car, some staunch supporters of DiBenedetto have been quick to criticize the new 21 program. “Matt has some very devoted fans, VERY. Whenever something happens to Harrison, anything short of the best possible outcome, the first reaction [on twitter] is ‘SHOULD OF KEPT MATT.’ It’s not a matter of what we wanted to do because we liked or didn’t like him. I’ve said it ten times already, I think more of Matt than I do most any driver I’ve ever worked with. Who could say that they’d make a decision for their family business solely because they like somebody over a decision to keep the business going? As much as we like Matt and think a lot of him, it was not going to work as a full time team going into the next gen. We had to do something different. You have to put your family, business, and employee’s well-being over friendships and emotions.”

There’s a lot of concern in Jon’s voice as we speak. He knows what it’s like to be on the receiving end of criticism, and what it’s like to be a young prospect with an uphill battle. Still, for the struggles on and off the track, Jon also knows the simple pleasures of being a professional race car driver.


“To this day I don’t really know how she found out…I think she found a gas receipt that proved my truck wasn’t really at the Charlotte airport like I said it was.”

The first thing I remember when thinking about Jon Wood, for better or worse, is an appearance he made on a reality show back in 2004. The SPEED channel produced a few episodes of “I Wanna Date a Race Car Driver” which featured drivers as the prize and supposed race fans chasing their romantic interests as contestants. If you’re too young to remember cable tv back then, consider yourself lucky, because reality dating shows were of particular interest and very cheap to make. At the time of the show’s production, Jon Wood was a 22 year old handsome professional race car driver that almost certainly didn’t think things out the way he would have today as the devoted family man he’s come to be. “I guess it was pitched to the PR at Roush, and at the time I didn’t think it was going to be anything memorable. I had a live-in girlfriend at the time, but I didn’t think it was a problem.” The show, from this writer’s imperfect memory, involved four girls that would have to compete in various challenges and embarrassing antics…I guess to score points? Either way, the driver would pick a winner and supposedly go on some sort of date at the end. Jon continues, “what I didn’t know was that the show would use a couple of race fans as contestants, but the other girls would be casting calls, you know…pretty hot, and that’s where I got into trouble. Maybe I got the girl’s phone number. Might have been calling her. Might have also went to Nashville one weekend while I still had this live-in girlfriend. I told her I was flying to Michigan for the Cup race, packed all my clothes like I’d be at the track…but I drove to Nashville instead and had a big old time. Might have.”

Long story short, and perhaps karma being what it is, Jon was found out, lost the girlfriend, and may never have seen the Nashville hook-up again. “…that’s a bummer, ain’t it? As cheesy as it sounds, it’ll be a story I remember forever.”

Race car drivers, man.

While not the proudest moment in NASCAR history, both Jon and team do have a veritable bounty of all-timer moments to choose from.


“I think David Pearson is the first name you think of, and that’s for obvious reasons,” says Wood, “but as a moment in history I think of something else.”

There was one talking point on my mind when thinking about this interview. I wanted to know who Jon Wood sees as the face of the Wood Bros as a driver, and what the greatest memory of the team should be. For all the struggles in the era of Jon Wood’s driving career: the sponsorship woes, the results below expectations, the DNQs, and the reduced Cup schedule, an unexpected beacon of hope came in 2011. “I think if you did a poll, most people would look at Trevor Bayne. First it was unexpected, but it’s also a great story for him and for us.”

Trevor Bayne’s 2011 Daytona 500 win not only put a young driver on the map, but may have helped the famous 21 team through its most challenging time. “There’s no way to measure how much one race affects a team, but with how everything went that day, I can’t help but think we’d be having a different conversation now. We could be talking about when we HAD a team. Penske, Motorcraft, all of what we have now, I can’t help but think that race is a big reason we are where we are today.”

Predicting the future is a tough racket in a sport like NASCAR, and nearly impossible when you apply it to any one particular person. There are a lot of options for a guy like Jon Wood, but total control of the team seems unlikely. Race teams typically don’t make it 72 years, and perhaps the family business style of the Wood Bros is a pivotal reason. “We’ve never been a single owner type of thing, it’s never been one person’s decision when we do things, and I think that’s our secret to surviving for this long. It’s not about winning races, it’s not about being great salesmen, or any of those things other teams excel in. It’s the one single trait that I’m most proud of and that I wouldn’t trade for anything, and that’s being honest people, and having people say nice things about you.” 

No matter the specific role, the future of the Wood Bros organization is likely to depend on Jon Wood, his cousin, and his sister who each have a share in the team and perhaps will run it more in the future. NASCAR is a humbling business, but Jon seems prepared. “I think I can do most of it, but the one thing I struggle with most is the ability to build the relationships, and keep them, which my dad is so good at. I know I can manage being one of those good honest people, but the relationships, that’s tough. As for what’s in my future, I don’t know. I know I want to keep this team going, and make it last longer than these 72 years, but there’s a lot I have left to learn.”

Via The Daytona Beach News Journal

Follow Matt on Twitter for more NASCAR thoughts and trips down memory lane.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s