Today’s NASCAR fans might see the likes of Denny Hamlin, Ross Chastain, or an earlier version of Kyle Busch as the sport’s bad boys. But if there were ever a crown for the most notorious driver in NASCAR, it would surely go to Robby Gordon. Though he clinched just three wins in his Cup series career, spanning 396 starts over 19 years, Gordon was better known for not playing nice, both on and off the track.

His knack for stirring up trouble was legendary. In just five years, he racked up fines totaling a whopping $290,000, all paid to NASCAR. But it wasn’t just his wallet that took a hit. His controversial statements and bold moves on the track didn’t win him any fans. Instead, they cemented his reputation as the quintessential “bad boy” of NASCAR, a driver who always seemed to be in the eye of the storm.

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Right from the start, it was clear that Robby Gordon was a force to be carefully measured up on the track. His aggressive style was especially prominent in the open-wheel circuits. But when he shifted gears to stock car racing, where the cars can take a bit more beating, he really started to make waves. His journey in this rough-and-tumble world began with a spat with none other than Tony Stewart, then a legend in the making.

Their first clash happened during a practice session for the Daytona 500. Both drivers were hot under the collar after their cars bumped. But this scuffle was just the beginning for Gordon, who was determined to show he wasn’t a pushover. Fast forward to the 2003 Dodge/Save Mart 350. With 38 laps left and under a caution flag, Gordon made a bold move. He passed his teammate and pal, Kevin Harvick, in a move that, while legal, didn’t win him any friends. In the end, he managed to fend off Jeff Gordon and clinch his second cup victory with the #31 RCR team. Harvick had to settle for third, and the racing world buzzed with Gordon’s unconventional tactics.

In 2005, during the Daytona 500, Gordon’s new #7 team found themselves in hot water. NASCAR slapped penalties on ten teams, including Gordon’s, for unapproved tweaks to their cars. Then there was the Sylvania 300 that same year. A crash with Michael Waltrip, driving the #15 NAPA Chevrolet, really got Gordon’s blood boiling. He even hurled his helmet at Waltrip’s car as it zoomed by, narrowly missing Tony Stewart’s #20. In 2006, at the Bass Pro Shops 500, Gordon stirred up controversy again. He allegedly tossed roll bar padding onto the track at the Atlanta Motor Speedway. This act brought out a caution flag, significantly affecting the race’s outcome, especially for Jeff Burton, a top contender who ended up in 13th place.

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But it wasn’t just his fiery confrontations that kept Gordon in the spotlight. His team’s risky on-track maneuvers and some rule-bending modifications cost him dearly in more ways than one.

Robby Gordon’s racing path was often rocky, dotted with hefty fines, and always under NASCAR’s watchful eye

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Back in 2008, at the famed Daytona 500, Robby’s car was caught with a bumper cover that didn’t meet NASCAR’s strict standards. The fallout? His crew chief Frank Kerr was benched for six weeks, slapped with a $100,000 fine, and put on probation for the rest of the year. But then on March 5, 2008, the National Stock Car Racing Commission decided to give back the points they had taken but upped the fine to a staggering $150,000. 

Robby’s run-ins with the rules didn’t end there. In 2009, after the Coca-Cola 600, his car was found with a rear toe setting that was more than just a bit off. While it might have given him an edge on the turns, the tweak cost him 50 points and his crew chief a hefty $50,000 fine. Robby chose not to contest the penalty.

2010 brought more headaches. Before a race at Darlington Raceway, inspectors found illegal parts in the car Robby owned and drove. The price for bending the rules this time? 25 points each from his owner and driver tally, a $25,000 fine for his crew chief Samuel Stanley, and a year-long probation. All these fines added up to a whopping $290,000 over five years.

The drama peaked in 2011 when Robby found himself on indefinite probation in NASCAR. This came after a garage area scuffle with fellow driver Kevin Conway on March 4. The tiff, fueled by mutual lawsuits, even led to Conway filing a misdemeanor battery complaint against Gordon. It seems Robby’s time on the track was as much about navigating controversies as it was about racing.

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