There is always a thin line in sports, of “What has been” and “What could’ve been.” All of human history throughout time has acted out on this one thin line. The world of motorsport is no stranger to the “What ifs” of the world. One such story was of NASCAR’s legendary driver Darrell Waltrip. Waltrip was hot property back in the 80s, and he had gotten the attention of the man whose name is synonymous with success, i.e., Roger Penske.

Both Waltrip and Penske are veterans of NASCAR who have seen the sport transition from grassroots to mainstream, and the chances of them working together were an actual possibility once. But a little thing called “Destiny” chose otherwise for both of them.

“Tear that deal up”: Roger Penske‘s sudden retreat from NASCAR comeback

Roger Penske has had impeccable success in multiple motorsport series. With 5 championships in NASCAR and 18 championships in IndyCar, one can say whatever the man touches turns to gold, but there was a time when that wasn’t the actual case.

In the 1970s, Penske fielded his cars in NASCAR, only to withdraw in 1977 because of no materialization of ambitions. A failed run at F1 only added to his early failures. After which he fully shifted his focus to IndyCar. But there was a time when Penske saw an opportunity to make a comeback with the prospect of winning it all with the NASCAR legend, Darrell Waltrip. Back in the early 70s, Waltrip was a young upstart rookie, and his calculative and tactical driving had almost laid the foundation for Penske’s homecoming.

As revealed by the NASCAR legend Darrell Waltrip to Dale Jr. during an appearance on the Dale Jr. Download: “I was going to drive for Roger Penske… So I go to Roger’s house in New York… Made a deal,” Waltrip shared. Everything seemed good. The deal was almost official, but things took a turn when Penske got a call. “Next day Roger calls me and said, ‘Hey, tear that deal up… deal’s off… The reason? … Bill Gardner called… said if I sign you to a contract. Neither one of us will be in racing anymore,” Waltrip recalled as part of the fascinating story about the potential deal that altered the trajectory of his career and NASCAR history.

It wasn’t the last time Gardner kept Waltrip from leaving his team. As they say, when things went well for Waltrip and DiGard Racing on the track, they went really well. After all, they won 25 races in a span of five years. However, Gardner didn’t want Waltrip to leave. His offer for Waltrip to drive for DiGard came at a time when Darrell Waltrip’s team desperately needed money. Yet, off the track, the two seemed to be in a constant tussle. This was evident when Ranier Racing came calling.

The team showed a lot of interest in Waltrip, offering a deal for him to join Ranier in 1978. But Gardner didn’t budge. The dream of Waltrip fell right apart once again. Bill Gardner, Waltrip’s then-team owner at DiGard Racing, intervened with the deal, which could’ve possibly cost Waltrip his dream. But as they say, “when one door closes, another opens.”

From Penske to Junior Johnson: A career-defining move

Things might not have gone as planned for Waltrip so far, but fate had chosen otherwise for him. When the Penske deal didn’t come to fruition, Waltrip completed the season with DiGard Racing anyway. But destiny knocked on his door one day in the form of Cale Yarborough. At the time, Yarborough was a 3x Champion, driving for Junior Johnson, and he approached Waltrip to take up his seat at Junior Johnson. “Cale put his arm around me and said, ‘Darrell, I’m going to tell you something. I’m leaving Junior’s, he said ‘I hadn’t told anybody. But here’s what I want to tell you: Junior Johnson wants you to drive his car.'” Waltrip recalled when Yarborough confided in him.

The revelation was shocking, considering Yarborough’s dominance at the time. More importantly, Yarborough told Waltrip that Junior Johnson wanted him of all people to take over the iconic car. For Waltrip, the opportunity to drive for Johnson was once in a lifetime. “Junior Johnson wants me to drive his car? That floored me,” Waltrip admitted. Then in the 1981 season, he started riding for Junior Johnson.

The move to Junior Johnson’s team proved to be the best decision ever. Waltrip went on to become one of the most legendary drivers in NASCAR, winning three championships with Junior Johnson. Waltrip’s career may have taken a turn with Johnson, however, the story of the Penske deal remains somewhat of a “what if” mystery in NASCAR history. Probably for the best, as Penske returned to NASCAR with an established IndyCar pedigree. Still, one can’t help but wonder how a Penske-Waltrip partnership in 1980 might have changed the sport’s landscape. For Waltrip, it was a reminder of how quickly fortunes can change in life.

So what are some of your favorite “what ifs” in Motorsports ? Let us know in the comments.