NASCAR legend admits ‘biggest mistake’ with Tony Stewart’s legacy was blessing Joey Logano

In the high-stakes world of NASCAR, every decision has a ripple effect that can alter careers, rewrite legacies, and shape the sport’s future. One such decision came when Greg Biffle, a NASCAR Hall of Famer, admitted that turning down the opportunity to replace Tony Stewart at Joe Gibbs Racing (JGR) was his “biggest mistake.” This pivotal moment not only changed Biffle’s trajectory but also paved the way for Joey Logano, a young driver whose career took off after stepping into the legendary No. 20 car.

The Pivotal Moment: Tony Stewart’s Departure from JGR

In 2008, Tony Stewart, a two-time Cup Series champion, made the bold decision to leave Joe Gibbs Racing, the team with which he had built his legacy. Stewart had won championships in 2002 and 2005, solidifying himself as one of the sport’s most dominant drivers. However, Stewart saw a bigger opportunity: team ownership.

Stewart’s departure wasn’t just about a career move; it was also deeply personal. JGR had switched manufacturers from Chevrolet to Toyota, and Stewart had always been loyal to Chevy. The switch played a significant role in his decision to leave the team, despite the success they had shared. Stewart’s exit left Joe Gibbs Racing scrambling to find a worthy successor for the coveted No. 20 car.

Greg Biffle: The Opportunity That Slipped Away

Amid the uncertainty, Greg Biffle found himself at a crossroads. A proven winner with Roush Fenway Racing, Biffle had already won championships in the Truck Series (2000) and Xfinity Series (2002). At the time, he was also competing at a high level in the Cup Series, making him a prime candidate to take over Stewart’s seat at JGR.

Biffle recently revealed on Dale Jr. Download, a popular NASCAR podcast, that he was offered the No. 20 seat. “I had the chance to drive for Joe Gibbs Racing when Tony left,” Biffle admitted. “But at the time, I felt committed to Roush Fenway Racing. I was competing for a championship, and I didn’t want to walk away from that.”

His decision to stay loyal to Roush Fenway seemed noble at the time, but in retrospect, it proved costly. While Biffle remained competitive for a few more seasons, Roush Fenway Racing began to decline, struggling to keep up with the increasingly dominant powerhouse teams like Hendrick Motorsports, Joe Gibbs Racing, and Team Penske.

Biffle never won a Cup Series championship, and by 2016, he had exited full-time racing. Reflecting on his decision, Biffle now sees it as the biggest regret of his career. “If I had taken that seat, who knows how things would have played out?” he wondered.

Joey Logano: The Unexpected Beneficiary

With Biffle passing on the opportunity, Joe Gibbs Racing turned to a young prospect: Joey Logano. At just 18 years old, Logano was still in the early stages of his career but had already made a name for himself as one of NASCAR’s most promising talents. Gibbs saw potential in the teenager, believing he could develop into an elite driver.

However, Logano’s first years at JGR were a struggle. He won just two races in four full-time seasons, failing to live up to the expectations that came with replacing a legend like Tony Stewart. Many in the NASCAR world questioned whether Gibbs had made a mistake by choosing Logano over a more experienced driver like Biffle.

In 2013, Logano made a career-defining move to Team Penske, where he finally began to fulfill his potential. Under Roger Penske, Logano blossomed into one of the sport’s top drivers. He won the Daytona 500 in 2015 and captured his first Cup Series championship in 2018. He added a second title in 2022 and a third in 2024, proving himself as one of the greatest drivers of his era.

Today, Joey Logano has 36 career Cup Series wins and multiple championships, cementing his place among NASCAR’s elite. What once seemed like a gamble on a young driver turned into a franchise-altering decision for Team Penske.

How Tony Stewart’s Decision Changed NASCAR Forever

While Biffle’s regret and Logano’s rise are key elements of this story, the real catalyst was Tony Stewart’s departure from JGR. Had Stewart stayed, JGR would have likely continued as a Chevy powerhouse, and the entire landscape of NASCAR might look different today.

Instead, Stewart’s exit led to a chain reaction:

• JGR doubled down on its Toyota commitment, becoming one of the most dominant teams in the sport.

• Stewart-Haas Racing was born, eventually winning multiple championships with drivers like Kevin Harvick.

• Joey Logano found his true home with Team Penske, developing into one of the best drivers of his generation.

Greg Biffle’s Career: What Could Have Been?

While Greg Biffle had a highly successful career with Roush Fenway Racing, it’s hard not to wonder what could have been had he accepted JGR’s offer. Driving for a powerhouse team like Joe Gibbs Racing, alongside elite teammates such as Kyle Busch and Denny Hamlin, might have given Biffle the final edge he needed to capture a Cup Series championship.

Instead, he remained loyal to Jack Roush, a decision that in many ways defined the second half of his career. By the time Roush Fenway Racing began its decline in the mid-2010s, it was too late for Biffle to move to a more competitive team.

Today, Biffle’s legacy is one of immense talent and near-misses. He remains one of the best drivers to never win a Cup Series championship, but his influence on the sport is undeniable. His story serves as a reminder that in NASCAR, timing and decision-making are just as critical as raw talent.

Conclusion: A Decision That Changed Everything

The saga of Tony Stewart, Greg Biffle, and Joey Logano is a fascinating look at how one decision can alter careers and reshape the landscape of NASCAR.

For Stewart, leaving Joe Gibbs Racing was a bold move that led to team ownership and further success. For Biffle, staying with Roush Fenway Racing instead of seizing the opportunity at JGR remains his biggest career regret. And for Joey Logano, stepping into Stewart’s shadow at JGR may have started rocky, but it ultimately led to a Hall-of-Fame-worthy career with Team Penske.

In NASCAR, as in life, the smallest choices can have the biggest consequences. Greg Biffle’s “biggest mistake” ultimately became Joey Logano’s greatest opportunity, proving that in racing, one driver’s loss is often another’s gain.