“He was ready to strangle me.” Those were Tony Stewart’s words when he recalled telling Joe Gibbs that he was leaving Joe Gibbs Racing (JGR). The two-time Cup Series champion had built a winning legacy with JGR, capturing titles in 2002 and 2005. But by 2008, Stewart wanted more. He saw an opportunity to be a team owner, just like Joe Gibbs. The conversation wasn’t easy. Gibbs, a former NFL coach turned NASCAR team owner, had invested heavily in Stewart’s career. Letting him go wasn’t part of the plan.

Stewart’s departure wasn’t just about finding a new challenge. JGR had switched manufacturers from Chevrolet to Toyota, and Stewart had always been loyal to Chevy. That shift played a significant role in his decision. When he told Gibbs he was leaving, the legendary coach was furious. But Stewart softened the blow when he explained his reason. “I have the opportunity to be like you,” he told Gibbs.

While this made Gibbs a little happy, the biggest concern was looming ahead. Who will replace the mighty Tony Stewart and take charge of No.20 Toyota? Joe Gibbs tried to connect with many drivers but eventually finalized teenager Joey Logano. However, almost half a decade after the incident, NASCAR Hall of Famer Greg Biffle revealed that he was also offered the iconic seat. The offer was real, the seat was his if he wanted it. But in a decision that haunts him to this day, he said no.

On the latest episode of the Dale Jr Download podcast, former cup driver Biffle revealed his reasoning behind the decision. “I got offers. Very thankful. I got offers all the time. (Best offer?) Drive the No.20 car for Gibbs. That was right before Logano went in it when Tony was leaving. I was (in a position to join JGR), but I was on the road to winning the title. I would have had to announce my championship title run in my first time in the Cup. I’m like, ‘I can’t do that.’ You know, this guy gave me a chance. I won a truck championship, an Xfinity title, and now I’m about to win the Cup title, and I’m going to sign with another team?” he recalled.

Notably, Biffle had a storied career with Roush Fenway Racing. He first caught the attention of NASCAR legend Benny Parsons in 1995. Parsons recommended him to Jack Roush, and that connection changed Biffle’s career. By 1998, he was the Truck Series Rookie of the Year. Two years later, he won the Truck Series championship. His success continued in the Xfinity Series, where he won the 2001 Rookie of the Year award and then the championship in 2002.

However, the NASCAR Hall of Famer never won a Cup title, and his decision to decline JGR offer to replace Tony Stewart proved a blunder. Over 14 full-time seasons, he secured 19 wins and finished in the top 10 in points six times. In 2005, he came painfully close to a championship, finishing as the runner-up. But things changed. By 2016, Roush Racing had declined. The team struggled with outdated equipment and couldn’t keep up with NASCAR’s growing competition. Frustrated, Biffle stepped away from full-time Cup racing.

Stewart, at the time, felt he should have led with the reasoning of wanting to follow in Gibbs’ footsteps. He explained, “I would have liked to have started that conversation with that quote, because I felt like I was this tall during that whole conversation until I said that to him. And when he stopped, it was like it flipped the switch. And how do you try to discourage somebody from trying to do what you’ve done?” 

On the other hand, Joey Logano had a blistering rise in his career. Just 18 years old, Logano took over Tony Stewart’s iconic No. 20 car in 2009. His early years at JGR weren’t easy. He managed only two wins in four seasons. But despite his struggles, his talent was undeniable. In 2013, Logano moved to Team Penske, a decision that changed his career. Under Penske, he flourished. He won the 2015 Daytona 500 and captured his first Cup Series title in 2018. He followed that up with another championship in 2022 and secured his third title in 2024. His dominance in the No. 22 Penske Ford has made him one of the most successful drivers of his era.

However, if Biffle had taken the JGR offer, Logano’s career might have looked very different. Instead, fate worked in Logano’s favor. Biffle’s decision, as he later admitted, was a missed opportunity. But it was also a blessing for Logano, who took the seat and turned it into a blistering career. While speaking about his own career mistakes, Biffle also revealed why Kurt Busch had an abrupt exit from Roush Fenway Racing.

Biffle opens up about Kurt Busch’s fallout!

Not every driver leaves a team on good terms. Some exits are filled with tension, and Kurt Busch’s departure from Roush Racing in 2005 was one of the most controversial in NASCAR history. Greg Biffle, Busch’s former teammate, recently shed light on what happened behind the scenes. Busch had been one of Roush’s top drivers. He won the 2004 Cup Series championship and was seen as a future star.

However, by 2005, tensions were high. Biffle revealed that Busch’s attitude and off-track behavior played a key role in his departure. “He didn’t get a DUI, but they stopped him… and I think he was a real a–hole to the cops,” Biffle recalled. The breaking point came in Phoenix, just miles from the racetrack. Busch was pulled over for reckless driving and allegedly made comments like, “Do you know who I am?” The incident led Roush to suspend Busch for the final two races of the season.

Biffle believed Busch’s frustration with the team contributed to the situation. “Kurt was unhappy,” he said. The team had already been looking to move on, and Busch’s off-track issues gave them the perfect reason. Busch moved on to Penske, where he had success, including a Daytona 500 win in 2017. But his career was never free from controversy. By 2023, he had stepped away from full-time racing because of injuries from a crash at Pocono. However, Biffle’s comments reveal that in NASCAR, one poor decision might change everything.