For the first time in 47 years, Darrell Waltrip doesn't know what's next

Darrell Waltrip, shown with wife Stevie, retires on June 23 after being involved in NASCAR for 47 years. Randy Sartin/USA TODAY Sports

CONCORD, N.C. -- Darrell Waltrip is holding court. He's got his foot up on a very expensive coffee table in former boss Rick Hendrick's very fancy office. His right hand, the one decorated by his NASCAR Hall of Fame ring, is fiddling with a Yeti cup while his left hand is in constant motion, illustrating and underlining and punctuating every point he's trying to make.

And there are plenty of them.

"Chevrolet came to me and said, 'We want you to hire this kid from California to drive for you.' I said, 'Who the hell is Jimmie Johnson?! He wrecks all the time! No!' I'm such a great evaluator of driving talent."

"I remember one time down at the Nashville Fairgrounds we were racing against Marty Robbins ..."

"You should have seen Robert Gee building race cars. Dale Junior's grandfather, welding like this: PFFFT ... PFFFT ... PFFFT. I was like, he's fixing my race car? This sumb---- can't even weld!"

"We were on an elevator at Bristol and these kids had their faces in their phones, until one of the dads said, 'You know, this is Darrell Cartrip from the 'Cars' movies.' That got their attention."

The one-hour conversation starts very relaxed. But like a good race car, the chat picks up speed as it goes along, with the same desperation that comes with trying to squeeze every ounce of whatever that machine has left in it before the checkered flag falls.

Waltrip's checkered flag comes in exactly one month with his last race in the broadcast booth. For 47 years, he has been paid to show up for NASCAR Cup series races, dating back to his big league driving debut at Talladega on May 7, 1972. From there, Waltrip went from being an unknown short-tracker from Owensboro, Kentucky, to becoming labeled as "Jaws," NASCAR's original smack-talker, who dared to rankle the likes of Richard Petty, Bobby Allison and Cale Yarborough. He's won 84 races and three championships, written a New York Times bestseller, appeared in multiple major motion pictures, and even earned an Emmy nomination. His phone hasn't stopped ringing for nearly half a century.

But after Fox signs off at Sonoma Raceway on June 23, he has no idea when or if someone will call him to come out to the racetrack again. He runs one hand through his gray hair. The shark in winter.

"When you talk about retiring or not being around the sport anymore, it's not the trophies or the wins or anything else. It's the people," Waltrip's said, with a somber tone as he points to the man standing behind the chair next to him. It's Rick Hendrick, who quietly nods in agreement.

"I've seen these people every weekend my whole adult life. When you're a part of something, you're a part of it. When you're not, when all of the sudden you don't show up, for just a few weeks, the next time they see you it's like they don't even know you. They just walk on by. 'Oh, hey, man.'

"This is my family. They've been my family for 50 years. Are they just gonna forget about me?"

Hendrick speaks up. "You can always come work here at my place and I'll go fishing. You can have my plane, my bus, my radio, the whole deal. I'll be over at the lake." The room erupts in laughter. Waltrip is smiling again. This happens multiple times over the course of the hour.

To the outsider, it might look a little odd, Rick Hendrick the NASCAR team owner handling Darrell Waltrip the race car driver the same way he probably did during their four years together as boss and employee. But that was 30 years ago, and it didn't exactly end on a high note, with Waltrip choosing to walk away from the "Dream Team" he and Hendrick had assembled -- and won a Daytona 500 with -- to start his own team.

It's only odd to us. To them, it's simply the nature of their friendship. And yes, it is a friendship. A great one. Hendrick has been soothing his friend's pain and providing him with guidance since long before those Tide Ride days of the late 1980s, and continues to do so even now. "Junior Johnson taught me how to be a championship race car driver," Waltrip says of his boss before Hendrick, with whom he won three titles in six years before bolting for Hendrick Motorsports.

"Rick has taught me how to be a businessman. How to work toward the next goal on the list. All the way up until right this moment, he's given me such great advice. Even when I was too stupid to take it."

While he was still driving for Johnson, Waltrip was struggling with owning a new Honda dealership in Tennessee. It was Hendrick who provided counsel and eventually became a partner in the venture, which is still thriving to this day. In 1990, just after Waltrip's disappointing tenure as a Hendrick driver was finally taking off (they won six times in '89, their third year together), he took Hendrick to lunch at the Mayflower Seafood Restaurant in Concord, North Carolina, and told him he was leaving to start his own team.

"He told me it was a terrible mistake," Waltrip recalls. "But he also said he wasn't going to stand in the way of a man's dream. So not only did he say he understood, he helped me build that team." A few years later, when Hendrick's warnings became reality and Waltrip's team was teetering on extinction, it was Hendrick who arranged a meeting with the businessman who bought Waltrip's team and saved it from ruin. Since the official announcement of Waltrip's retirement, he has repeatedly called Hendrick to go over the financials of his next step. "At the dealership they say, 'Darrell, we need you to sign this,'" he explains. "And I say, 'Great, has Rick signed them?'"

These are the topics of conversation that Waltrip rifles through on a Tuesday morning during Charlotte Speedweeks. It's a series of thank-yous to Hendrick. But there's also a list of what-ifs about his legendary career. What if he had stayed with Junior Johnson? ("I might have won some more races, but Rick offered so much more money that even Junior was like, 'You gotta take that deal.'") What if he had been more careful about piecing together that Dream Team in '87, a group that included the All-Star likes of Waddell Wilson (elected to the NASCAR Hall of Fame this week), Eddie Dickerson and Gary DeHart but that completely fell apart by season's end? ("We needed one leader, not seven, and we had seven.") What if he had taken Hendrick's advice and stayed in the HMS fold instead of falling for the 1990s' driver-owner fad? ("I might have seven championships and 100 wins. Heck, I know I would.")

This is what all 72-year-olds do as they march toward the uncertainly of retirement, whether it be a gold watch and a goodbye cake in the break room or a video tribute shown to millions at the end of a sports telecast. His driving retirement tour in 2000 came with all of the above, with rocking chairs and flip-card stunts from Rockingham to Bristol. But during all of that, Waltrip knew what was coming next. This time around, he does not.

"My bosses at Fox have said they want me to still be a part of the team. They will find something for me to do. But I think Rick will agree with me on this, that when you've been to the top of mountain and that's where you've always been, and then they want to put you down here. Something else. You're still on the mountain, but you're on the bottom, not at the top. That takes some time to digest. Do I want to work my way back ... ? Or do I want to just leave it there and forget it?"

When Jaws arrived in the 1970s, he made his name by calling out the veterans and embracing the media that the old guard resisted. When he moved into the broadcast booth in 2001, nearly a decade after his last win, he became invigorated by trying to work against the crusty old conventional habits of the color commentator's gig. (Say what you want about "Boogity! Boogity! Boogity!" but it is instantly recognizable even to non-NASCAR fans and it still sells lots of T-shirts.) That guy, his worst nightmare is to become one of the fossils he always took pride in pissing off, an old man trotted out to sign autographs at the NASCAR Hall of Fame and car shows to a smattering of aging applause.

Again, Hendrick jumps in. Doesn't DW remember all those stories he told earlier, about Marty Robbins and Junior Johnson and passing on Jimmie Johnson? Why not get a producer and tell those stories? Hendrick offers to start making phone calls instantly. "People are craving that," he says. "And you're the guy to do it. Make it your project. You're in charge. I know you like being in charge." Again, there is laughter. "This summer, you need to sit down and list the 10 things that have happened to you that mean the most to you in your life, outside of your wife and kids," Hendrick suggests. "You revolutionized this sport. No one else would talk. You took on the establishment. I look at what you did and I compare it to what Jeff [Gordon] did. You became an owner and you didn't have to close shop, and you won races. ... You helped build all of this. Don't ever lose sight of that."

And again, Waltrip beams. "See? When I get down and get discouraged, that's why I call him."

No matter what Waltrip's third act might be, he knows that Hendrick will continue on. The long-labeled "Most Powerful Team in NASCAR" has struggled in recent years, stumbling as its driver roster's average age has plummeted with the retirements of Dale Earnhardt Jr. and Jeff Gordon. But those woes certainly aren't limited to Hendrick Motorsports. As uncertain as Waltrip might be about his own future, he sees just as much haziness when he looks into stock car racing's crystal ball.

"Am I happy with where the sport's going? I don't know. I have questions. I've had so many crossroads in my career, and that's where NASCAR is, at a crossroads. It reminds me of when Petty and David Pearson and those guys were slowing down and here was me and Dale [Earnhardt Sr.] and Rusty [Wallace] and people were like, 'Who is this bunch of punks?' They didn't know anything about us.

These young guys coming in now, we don't know anything about them. Who's going to step up? Who's gonna fill their shoes? Well, you don't fill shoes. You build your own deal. You build your own era. Petty had his, I had mine, Jeff and Jimmie had theirs. So, who is next? Who is going to be the guy? I don't know." He goes through the names of Chase Elliott, Kyle Larson, Ryan Blaney and others. "We're at a crossroads with drivers, with sponsors, everything. And when you're at a crossroads, it's up to leadership to decide, are we going up or down? I question decisions every day that are made by NASCAR."

Waltrip talks about the importance of being able to take issues to the "head of the stream" and mourns the loss of the man who was once his greatest adversary, deceased NASCAR chairman Bill France Jr.

Waltrip points at Hendrick again.

"I'm pretty sure he questions those decisions, too. But he's in a different situation than I am. If he started telling you what he thought, he'd probably be joining me in retirement. I can tell you whatever I think because what are they going to do, fire me?"

As the prescribed hour for this conversation ticks toward its end, Darrell Waltrip is no longer spinning yarns, fixating on the rearview mirror or expressing apprehension about what lies ahead. Here, with the checkered flag in sight, Jaws returns.

"I sit in meetings every week and I wonder, what the heck are people thinking? So, there are plenty of people who I'm sure are sad to see you go, but they are also glad you are out of their hair. I came into this sport asking why, and I'm going to leave asking why.

"It's a tough time to be in the sport. It really is. It's probably a good time for me to step aside. Because I'm old-school and it will never be the way it was. And I don't think I can tolerate the way it's going to be."