NASCAR is built on moments of triumph and heartbreak, where races are won or lost by the finest of margins. Some victories define careers, while others slip away, leaving behind a trail of ‘what ifs’ that haunt drivers for years. Greg Biffle knows this feeling all too well. His career had all the makings of legendary status, with wins in the Truck, Xfinity, and Cup Series. Still, one missing piece prevented him from making history for the elusive NASCAR Cup Series championship. And if there was ever a race that encapsulated the agony of a dream slipping away, it was the 2005 season, where Tony Stewart’s championship bid unknowingly stole Biffle’s one shot at making history.

For Stewart, the season was a masterclass in consistency and dominance. He entered the season finale at Homestead-Miami Speedway with the championship virtually in the bag. But for Biffle, this was a different kind of race one where the regret of what could have been weighed heavily. This wasn’t just about a single event; it was about an entire season that unraveled in ways that still torment him today. His best chance at the ultimate trifecta winning championships in all three national NASCAR series was within reach, only to be taken away, leaving him with a career-long regret. And at the center of it all? Tony Stewart.

Greg Biffle recalls the moment he lost the championship

For Biffle, the heartbreak of 2005 wasn’t limited to Homestead. His real regret traces back to Texas Motor Speedway earlier in the season, where a loose wheel turned what should have been a defining race into a nightmare. He was in prime position to challenge Stewart for the title, running in third place when disaster struck. A critical mistake by his pit crew a loose wheel forced him to make an unscheduled pit stop, costing him a lap and sending the order down to a 20th-place finish. Those lost positions became the dagger in his championship hopes.

“We had left a wheel loose,” Biffle recalled while speaking on Dale Jr. Download. “Out of anything in my career, that eats at me. We lost the championship by three positions to Tony Stewart. I was running third, and we had to pit again. That cost us a lap, and we finished 20th that day.”

It was a gut-wrenching blow. A season’s worth of effort had unraveled in a single pit stop. If he had finished just three positions higher in the final standings, he would have taken the championship away from Stewart. Instead, he was left wondering what could have been, while Stewart went on to secure his second Cup Series title.

By the time the championship battle reached Homestead-Miami Speedway, Stewart only needed a solid finish to secure the title. But Biffle still had something to prove. He knew his title hopes were over, but a victory at Homestead could serve as a small consolation prize. And when the checkered flag fell, it was Biffle, not Stewart, who enjoyed the triumph of championship glory.

In a dramatic finish, Biffle held off teammate Mark Martin to claim victory, with Stewart crossing the line in 15th, securing the championship but missing out on the statement win that would have capped off his dominant season. Biffle’s victory was bittersweet it was proof that he was capable of winning when it mattered, but it was also a reminder of the title that had slipped through his fingers. Although there was no argument to be made about the point tally, the former Roush Racing driver had his doubts about officiating during the race in Texas.

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Did NASCAR Play a Role? The Championship That Could Have Been

Biffle’s frustration with how the season played out led to lingering questions about whether the deck had been stacked against him. In an era where conspiracy theories ran rampant in NASCAR, some couldn’t help but wonder if external forces had influenced the outcome.

“I’m not going to say NASCAR played a role in that, but… Matt [Kenseth] won it in ’03, Kurt [Busch] won in ’04, and I was going to win it in ’05. I think, you know, maybe the deck was stacked against us a little bit,” Biffle hinted in an interview.

While it’s easy to speculate, the reality is that NASCAR championships are often decided by the finest margins. One mistake, one stroke of bad luck, or one strategic misstep can mean the difference between legendary status and a career-long regret. And for Biffle, that regret remains as fresh as ever.

To understand the weight of this moment, one has to understand who Tony Stewart is. He wasn’t just another championship contender he was a driver who had built a reputation for being relentless, aggressive, and strategic. He knew how to position himself to win titles, and in 2005, he did just that.

Stewart wasn’t handed the championship he earned it through consistency and skill. But that doesn’t change the fact that Biffle’s misfortune played a significant role in the final outcome. If Biffle’s pit crew had nailed that stop at Texas, if fate had been just a little kinder, Stewart might not have been celebrating his second title that year.

Stewart’s victory was well-deserved, but the championship fight could have been very different if Biffle had been given the chance to go head-to-head with him in the final races. Instead, Biffle was left with one of the most painful ‘what ifs’ in NASCAR history.

Even today, no driver has won championships in all three of NASCAR’s top series. Biffle had the best shot, and that alone makes his near-miss in 2005 all the more painful. Stewart went on to solidify his legacy as one of NASCAR’s greatest drivers, later adding a third Cup Series championship in 2011 and transitioning into a successful team owner. Biffle, meanwhile, continued to be a strong competitor but never got another serious shot at the Cup title.

So, was Biffle truly robbed of his place in NASCAR history, or was it just another case of racing’s unpredictable nature? That’s the beauty of the sport the line between fate and strategy is always blurred.