The Wonder Boy Of NASCAR
Jeff Gordon may be one of the fastest drivers to ever hit a racetrack, but his life wasn’t always as golden as it seems. He had to overcome the kind of challenges that would’ve probably stopped anyone in their right mind—both before and after becoming one of the biggest winners in NASCAR history.
1. He Was Born For It
Born within miles of the California Speedway in the early 1970s, Gordon hit the racetrack way earlier than any of his peers. Thanks to his stepdad, he started riding BMX bikes at age four, and made the jump to racing with other kids in quarter midgets at age five. He boasted over 100 career wins by the time he was 11, which makes his next move pretty surprising.
2. He Got Tired Of It
Gordon seemingly made an attempt to retire from racing altogether at 12 years old. Reportedly, he became disinterested in racing, and decided to try his hand (and feet) at waterskiing. It didn’t take too long for him to ditch the water to return to the track, but when he did, he found a racing community that didn’t actually want him there.
3. He Was Too Young
With Gordon set to return to racing, his father searched for opportunities for his son to advance in the sport, which started with getting him a new sprint car. When he contacted former driver Lee Osborne to make Gordon a car, the man flat out refused when he found out the driver was only 13. After some convincing, Osborne complied—but that turned out to be just the beginning of their troubles.
4. They Tried To Stop Him
Age restrictions in California racing kept Gordon from competing in his own state, so he headed to Florida in the mid 1980s to try racing with the big boys—men more than twice his age! Florida technically didn’t have an age limit, but seemingly only because they didn’t think they’d need one. When a teenage Gordon arrived at Speedweek, people started to talk, and they didn’t have good things to say.
5. They Snubbed Him
Several people tried to stop Gordon from actually competing, from other drivers to fans and, ultimately, the owner of the raceway. But with no rules to keep him off the track, Gordon buckled in for his first race with the big boys. Unfortunately for him, though, things didn’t go quite like he hoped.
6. He Flopped
Gordon’s very first practice session at the speedway seemed to prove all his naysayers right. He got off to a very slow start, and once he actually did get going, he ended up hitting the wall and making a pretty dismal showing in front of his very adult opponents. He got so upset that he tried to call it quits that same day. He didn’t actually give up, though. In fact, he came back with a vengeance.
7. He Blew Them Away
By the end of that Speedweek, Gordon proved himself worthy of competing way out of his age range. He didn’t actually win any races, but raced fast enough to qualify him to race with some of the most experienced drivers on the track. In other words, he earned a name he’d soon be dubbed—Wonder Boy. But even with all those wins, his age still proved to be a huge hurdle to him moving up in his career.
8. They Held Him Back
Back at home in California, Gordon still struggled to receive permission to race with the older men. All things considered, the races posed serious danger for grown men, and even more so for a young boy. But still, both Gordon and his stepdad pressed for more opportunities. And eventually, they made a decision most parents would never even consider.
9. They Emancipated Him
Before the end of the year, their saving grace came in the form of attorney Cary Agajanian. He worked with Gordon's parents to get their son a partial emancipation. In other words, Gordon essentially became an “adult” at 13, with the ability to sign his own waivers before hitting the racetrack. That helped the situation, but they ended up doing something even more drastic to give him what he needed to speed to victory.
10. They Made A Move
Finally, after seemingly doing all they could, Gordon's family picked up and moved to a state with much more freedom for young racers—Indiana. From there, Gordon’s career took off. He spent the rest of his teen years and early twenties racing at increasing levels of difficulty and securing record shattering wins, including becoming the youngest driver in the World of Outlaws series and the youngest to win the USAC Silver Crown. By the turn of the decade, Gordon found himself primed to make even more history, in both his career and his personal life.
11. He Hit It Big
Gordon officially began racing with NASCAR in the early 1990s. And with that step, he seemed to finally reap all the rewards of his unusually hard work. He came in hot, winning Rookie of the year in his very first year out and continuing to race to success over and over again. But while he probably should have been focusing on his quickly escalating career, something even hotter than his wheels caught his full attention.
12. He Had A Huge Crush
All things considered, many men probably fell in love at the first sight of Miss Winston Cup model, Brooke Sealey. With beauty being part of the requirement for her job as a representative of the NASCAR sponsor, Sealey probably had several men on the ready to bow down and admire her. Perhaps that explains what Gordon went through in trying to catch her attention.
13. She Made Him Shake
Reportedly, Gordon needed to overcome a serious set of nerves to actually get to the point of asking Sealey out. In fact, Sealey herself noted that the day Gordon finally got up the courage to ask her out, she could hear his voice trembling. But, all things considered, it seems Sealey’s undeniable beauty wasn’t the only thing giving him reason to fear…
14. They Were Taboo
Reportedly, the big money players in the NASCAR organization considered it pretty taboo for their drivers to date any of the gorgeous Winston girls who worked alongside the drivers. And with Gordon’s star rising, he didn’t seem to think it would be a good look for him to date the racing hottie. So what did he do? He learned how to keep a secret.
15. They Kept It On The Low
Sealey and Gordon began dating in secret in 1993, and managed to keep things under wraps for quite some time. Perhaps they have the lack of social media platforms in existence at that time to thank for that. Either way, though, they couldn’t keep it a secret forever. And when the truth did come out, things didn’t quite go how they expected.
16. They Went Public
Once Sealey’s term as Miss Winston Cup ended, the new couple went public in a pretty dramatic fashion. They showed up to NASCAR’s award banquet in December 1993. Rather than shock and discomfort, fans responded with huge applause. They immediately became a NASCAR it-couple, and married the following year. Unfortunately for them, though, the fame didn’t turn out to be all fun and games.
17. They Had To Run
The new couple settled down in a house in North Carolina—or, at least, they tried to settle down. By then, Gordon’s fan base became so obsessed with him that they consistently tried to get to him at his own home. Eventually, things got so bad that they moved to a more private home in Florida. But it turned out to be only the beginning of the troubles that come with newfound fame.
18. They Looked Down On Him
Even though he seemingly proved himself in his first year with NASCAR, some naysayers still considered him too young to compete with the “big boys”. Now in his early twenties, Gordon still maintained quite an age gap with the other drivers at his level. And judging by the way he handled his race cars in those years, he seemed to prove them right.
19. He Did Too Much
All wins aside, Gordon still struggled with a tendency to push his cars too much, seemingly going too fast too soon. This resulted in multiple crashes in those years. Another driver even noted that he “hit everything but the pace car”. Still, Gordon held his own, ultimately making a place for other young drivers to join the ranks. And when he really found his groove, he became unstoppable.
20. He Won It All
For several years, it seemed Gordon just couldn’t lose. He didn’t win every single race he competed in, but his times consistently put him in top rankings. He wrapped the decade with several Winston Championships, including one in 1995, 1997, and 1998. And to top it all off, Gordon’s reputation got the good old conservative boost early in his career…
21. He Got Religious
By his own report, Gordon became curious about Christianity when he first started racing with NASCAR. Several of the other drivers attended church weekly, and he started to join them. He eventually professed to be a Christian, and even taped Bible verses to his race cars. The very traditional 1990’s America probably ate that right up. But don’t think he got away with his “innocent” image forever.
22. Things Got Sticky
One of Gordon’s most memorable racing controversies came about during the 1998 season. He didn’t get off to the best start in the New Hampshire Farm Aid on CMT 300, spending more than half the race around the middle of the competitors. And when he stopped at the pit to get his car refreshed, he made an intriguing choice…
23. He Had A Quickie
Rather than getting all four of his tires replaced like several of the other leading drivers did, Gordon only replaced two. With that unusual choice, he somehow managed to beat the competition with less than a third of the race to go, finishing in first place. The guy that came in second after leading most of the race didn’t take things too well.
24. They Accused Him
Another well known racer, Mark Martin, finished second. When he did, his team owner raised the alarm on Gordon, essentially calling him a cheater. He went straight to the NASCAR organization, insisting that Gordon and his team used some type of prohibited tire softener, causing him to win the race. As you can imagine, Gordon and his team didn’t take that accusation lightly.
25. Things Got Crazy
The issue continued to escalate as the rumors circulated among drivers and fans. For the most part, Gordon himself managed to stay out of the fray, but the spotlight stayed on him as his team owner publicly criticized the opposition. In the end, NASCAR seized Gordon’s tires to make an official assessment—and came up empty. Gordon kept his win, but something else soon arose to besmirch his “good guy” image.
26. The Fairytale Ended
The news came as a shock in March 2022. Gordon’s wife sued him for divorce. The end of a marriage is almost never a good look to the public eye, and in this case, people didn’t seem to expect it from this celebrity couple. But things took a turn for the worse when Sealey went public with the real reason she wanted to get away from her husband.
27. He Had A Wandering Eye
Sealey alleged that Gordon cheated on her during the marriage, in particular with another model and playboy cover girl, Deanna Merrymen. That probably doesn’t come as a surprise to you—rich men with rich men’s access have a history of getting around. But Gordon’s fans turned on him, especially when news of his mistress got out. Although Sealey’s next move made them rethink everything.
28. She Made Some Extreme Demands
The public got suspicious about Sealey’s motives when they heard about everything she wanted in the divorce. Her demands included the couple’s house and two cars as well as half of the millions of dollars Gordon made in his career. She didn’t stop there, either.
29. She Wanted It All
Sealey really wanted to squeeze her failed marriage dry. She also wanted alimony, and access to an airplane and their boats. But, of course, Gordon didn’t let that go so easily.
30. He Fought Back
Gordon and his representation countersued, insisting that regardless of the laws of the land, his soon to be ex-wife didn’t deserve to get half of the money he earned throughout his long, risky career. Sealey responded to that by insisting that “NASCAR is a relatively safe occupation”. I can’t say the stats necessarily agree with that statement, but in the end, she walked away a winner.
31. She Got A Fat Payday
After a little over a year of the lengthy, gossip-inducing divorce proceedings, Sealey walked away with a cool $15.3 million. Losing his nearly decade long marriage likely weighed on Gordon the way the end of most relationships do. But as a celebrity, he lost even more than his life partner and his money…
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32. He Messed Up His Image
The very public divorce and scandalous cause of it officially changed the public’s perception of Gordon as one of the “good ones”, so to speak. Even worse than that, he lost at least one major sponsorship deal due to the fact that they didn’t want him to represent them anymore. And how did Gordon take it, you ask? Maybe not quite how you might expect.
33. He Kept It Moving
Perhaps Gordon’s speed on the racetrack translated to his personal life, considering how quickly he moved on from his marriage. The very year the courts finalized his divorce, the public spotted him with another model—Amanda Church—chilling on a beach in the Caribbean. He escalated the situation even further with his next move. Quite Literally.
34. He Moved In
Just a short while after being spotted with his new boo, Gordon reportedly moved into her New York home and began living with her. For all practical purposes, he seemed to be doing just fine. Better than fine, even. But maybe the divorce actually did affect him more than he let on, considering some major missteps that came in his career shortly after.
35. His Luck Ran Out
Things seemed to be going well for Gordon at the start of his early 2000s racing seasons. He won several big wins across the globe, managing to hold his spot as a top driver. But in 2004 things changed.
36. He Lost His Crown
A new playoff system knocked Gordon from the top spot and landed him in third, despite the fact that he’d earned a championship win by the previous standards. The following season turned out even more bleak.
37. He Fumbled
Gordon continued to struggle as he went into his 2005 and 2006 season. It seemed his season of domination went the way of his marriage—to ruin. He stayed in the game though, despite hitting a career low in 2005. And while he managed to achieve some major success in 2007, it didn’t come anywhere near his first year with NASCAR. Perhaps he found himself a little too caught up in other, more fame-seeking pursuits.
38. He Started Out Different
Earlier in the 2000s, reporters asked Gordon if he was interested in a career on screen. This seems feasible, considering his popularity at the time and the way many celebrities try to amp up their fame by increasing their visibility. But Gordon answered with a resounding “Heck no”. Yet, just a few years later, he completely changed his tune.
39. He Made His Debut
It’s not clear what made him change his mind, but while he struggled to keep up his reputation as an all time champion in the world of NASCAR, he made several film appearances. This included cameos in the 2003 film, Looney Tunes: Back in Action and the 2004 film Taxi. But when he did have to make a choice between starry Hollywood and his racing, he fell back on old faithful.
40. He Wanted A Change
In 2006, the opportunity to play a role in the comedy film Talladega Nights: The Ballad of Ricky Bobby came around. The film centers on a pretty hokey but wildly successful race car driver who had it all until a new, faster driver shows up to threaten his reign. Gordon initially expressed interest in the fun story, but this time, he just couldn't have things his way.
41. He Had To Protect His Image
Gordon ended up turning down the opportunity in order to preserve his relationship with his sponsors. Perhaps they felt he’d done enough to tarnish his image, and didn’t want him associated with the film’s raunchy humor. Either way, he seemed to move on from any serious interest in film. But his thoughts on a movie career didn’t prove to be the only thing he changed up over time.
42. He Ditched His Beliefs
By the 2000s, Gordon strayed from the religious beliefs he seemed to hold so dearly at the start of his career. In fact, he told reporters he had “a difficult time focusing on a particular faith”. Now, considering the tricky way the Christian church seems to handle divorce and remarriage, perhaps that had a lot more to do with something else that he got up to just around that same time…
43. They Had History
Gordon met his future second wife, Ingrid Vanderbosch, back in 2002 during a visit to the Hamptons. If you’ve been paying attention, you’ll remember that’s just around the time Gordon’s first wife filed for divorce. And if you’re wondering—yes, Vanderbosch also modeled. The guy clearly had a type. Reportedly, though, nothing sparked between them until a bit later..
44. They Did It Differently
This time around, Gordon made sure to keep his relationship well out of the limelight. Reportedly, they started dating in 2004, and got engaged in June 2006. But even after Gordon asked Vanderbosch to marry him, they kept their plans under wraps for another month. And when they did tie the knot, they stayed so quiet that they shocked people.
45. They Didn’t Tell
Gordon and Vanderbosch kept things so undercover that even some of their closest friends didn’t know when they tied the knot in Mexico in November 2006. Instead, some of their peers learned the news from a surprising source.
46. They Shocked Their Friends
Gordon’s buddy Jimmie Johnson reported his own shock when he found out about the wedding on a tv show after the fact. Perhaps Gordon finally learned his lesson about life in the limelight, and just in time too. With the trouble on the horizon, he needed a strong foundation to stand on.
47. He Floundered
Gordon continued to blunder his way through his late 2000s seasons. In fact, between 2008 and 2010, Gordon reportedly only secured one win, at the Samsung 500. But don’t get things twisted. He didn’t rack up the wins the way he did the decade before, but he still bested a large majority of racers competing at the time. And when it came to what really mattered, he won big time.
48. He Made Bank
Even with his misses, Gordon still managed to beat out every other NASCAR driver when it came to his overall career earnings. In 2009, he officially set a new earnings record as the first NASCAR driver to make more than $100 million dollars in wins. Furthermore, he’d started racing a lot earlier than his competitors, so by the 2010s, he found himself prime to break even more records.
49. He Made His Name Known
In 2011, Gordon officially broke the record for most wins of any other NASCAR driver ever, cementing his name in the history of the sport. Now, if it were me, I’d take that as a good place to step down or retire—to take my wins and end my career on a high note. But that’s not what Gordon did, and considering a shocking incident the very next year, maybe the pressure of it all finally got to him.
50. He Had A Rough Start
Gordon experienced another rough start when it came to the 2012 season. He made many missteps that caused him to miss ranking in the top 10 in points that year, including a crash and car trouble. But during a race that November in steamy Phoenix, Arizona, the heat turned up way too high.
51. They Did Him Dirty
At the very beginning of the race, Gordon got off to an excellent start. But during those early laps, one of his hottest competitors, Clint Bowyer, brushed his car and caused him to hit the wall. The consequences were horrifying.
52. He Fell Behind
Bowyer’s interference delayed Gordon, causing him to fall back a bit. And while this likely couldn’t be the first time this happened to him, this turned out to be the time he just couldn’t take it anymore.
53. He Fought Back
Gordon attempted to get back at Bowyer, and ended up cutting his own tire in the process. Protocol mandates drivers to return to the pit to fix their tire during the race if that happens, but Gordon seemed to only care about getting back at his competition. The referees waved a black flag, signaling Gordon to stand down and exit the race. He did quite the opposite.
54. He Went After Him
Gordon went after Bowyer, wrecking his car on purpose. Bowyer stood as his prime competition for winning the Cup that year, so his shenanigans essentially snatched that opportunity away from him. The saga didn’t end there though. As a matter of fact, things continued to careen downhill once the two cars collided.
55. They Got Into It
Both of the men's crews climbed out of their pits and went after each other. Meanwhile, Bowyer managed to get out of his wrecked car and attempted to go after Gordon. Luckily for both, I presume, officials had already caught up with Gordon and restrained him, keeping things from getting even messier. In the end, though, he somehow still came out on top.
56. He Got Away With It
Ultimately, officials dealt Gordon a hefty fine for his behavior—a whopping $100,000. They also took away 25 of the points he accumulated over the season, and placed him on probation. However, it didn’t seem to affect him all that much, considering what he managed to accomplish the very next week…
57. He Couldn’t Be Stopped
The very next week, Gordon competed in the season's finale, the Ford EcoBoost 400. He seemingly raced to that win with ease. And with that, he earned enough points to make up for his deduction and landed his 87th Sprint Cup. If that’s not a “wonder boy” moment, I don’t know what is. But as reluctant as Gordon seemed to move on from racing, he eventually had to. And if you didn’t already guess, he didn’t go quietly.
58. It Got Away From Him
Despite decent wins in the 2014 season and the declaration of “Jeff Gordon Day” in Indianapolis, Gordon’s success on the racetrack clearly started to wane. Now in his early 40s, he found himself far from the young buck he’d been when he joined the sport.
59. His Age Caught Up To Him
Thanks to his own achievement, Gordon found himself up against younger, better racers. And as his status slipped away, he found it harder than ever to take his losses like a good sport. During a 2014 season race in Texas, Gordon’s temper flared up again in a shocking way.
60. He Got Too Heated
This time, things got messy as he raced to a leading finish with another driver. Just before the finish, another driver, Brad Keselowski, cut between him and the other person competing for first. Gordon's tire got caught and he spun out of control, ending up in the 29th place. His fury finally erupted.
61. He Confronted Him
With his pit crew there to back him up, Gordon confronted the driver who spun him out. Things did escalate into a physical encounter, but luckily for him, he actually managed to stay out of that part this time.
62. He Was At The End Of His Rope
Gordon got away unscathed, and ultimately admitted that the realization that he might never win another championship contributed to his emotional state. Finally, Gordon found himself at the end of his rope. Kind of.
63. He Tried To Give It Up
Gordon declared the next year, 2015, to be his last year of racing after the wrap of the previous season. He finished that year with only one win under his belt, though his overall points qualified him for the NASCAR Championship. Unfortunately for him, though, he finished in sixth place, just in time to wrap up his long racing career. Or not.
64. He Couldn’t Let Go
Despite his retirement, Gordon showed up again for the 2016 season. All things considered though, he actually stepped in to replace an injured teammate. So perhaps his return had more to do with helping his team than giving himself one final hurrah. And once he wrapped that season, he officially moved on with his life. He didn’t go too far, though.
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65. He Got His Screen Time
Although he never did make much of his foray into film and television, Gordon found himself a cozy spot on screen once he retired from the racetrack. It turned out to be the perfect fit.
66. He Brought His Skills To The Table
He almost immediately transitioned into a TV commentator for NASCAR racing in 2015, using his experience to beef up his skill with commentary. Even so, though, racing didn’t turn out to be the only thing he was a genius at.
67. He Made His Money Work For Him
As he grew older and considered his life after racing, Gordon used his wealth to start and contribute to various business ventures, securing his fortune for generations to come.
68. He Was A Businessman
Gordon’s successful enterprises include JG Motorsports, a car dealership, a clothing line, and a real estate company. Notably, even with all his wealth, though, he still found time and opportunity to ensure he gave to those in need.
69. He Loved The Kids
Gordon seemingly held a soft spot for children, and ultimately focused much of his charitable giving on them. He established the Jeff Gordon’s Children Foundation in 1999, and opened a children’s hospital in 2007 with several other well known names in sports. While he certainly experienced his share of ups and downs in his crazy pursuit of being the best, there’s really not much confusion about why people call him a wonder.
70. He Made History
Even though he’s been retired for nearly a decade, Jeff Gordon still holds many of the records he set during his time with NASCAR. He still holds the record for the most wins in NASCAR history, and is one of the top 20 highest paid athletes of all time sitting at a cool $515 million in career earnings. Without him, NASCAR likely wouldn’t be the household name it is today.