Back in 2007, Dale Earnhardt Jr. found himself at a crossroads. Following a fallout with DEI owner, Teresa Earnhardt, Junior decided it was time to forge his own path on his own terms. The announcement arrived monumentally, and unsurprisingly, several teams coveted what he brought and represented.

Dale Jr. approached three of NASCAR’s top teams regarding potential Cup Series opportunities. However, the young duo of Dale Jr. and his sister, Kelley Earnhardt, were simply unprepared for what awaited them during one of those meetings – so much so that it left him physically uncomfortable.

While discussing his career’s biggest decision, Dale Jr. shared a telling story about his meeting with Joe Gibbs.

“I went all the way to Washington to meet with Joe. And we were at Dan Snyder’s house… Really intimidating, honestly,” Jr. said on his podcast, Dale Jr. Download.

“It was hard to think about racing and working with Joe, and in that environment, it was hard to like think about what racing at Joe Gibbs would be like. And Joe gave us a term sheet, and the numbers on that made me physically nauseous because it was so big.

“I was like, “Holy f——g s–t Kelly.” I said, “We got to go home.” I was like, “We got to go home. We got to talk. We got to go home. Like I don’t know what Rick’s going to put in front of me. But I’m ready to leave.”

Joe Gibbs Racing was undoubtedly one of NASCAR’s premier organizations in 2007. Naturally, the team wasn’t going to hold back when pursuing Dale Earnhardt Jr. The Earnhardt name alone carried immense value, and top-tier teams typically viewed driver signings as long-term investments rather than short-term experiments.

In Junior’s case, Gibbs likely already had a long-term vision in mind and presented him with a contract he believed reflected that commitment. He was already the sport’s Most Popular Driver – a title he’d go on to claim 15 consecutive times from 2003 to 2017.

But as Earnhardt Jr. later explained, he was already dealing with immense pressure after deciding to leave his father’s team, Dale Earnhardt Inc. At a vulnerable moment, with only his sister Kelley by his side, he struggled to comprehend his true value in the driver market. The numbers being discussed felt almost too large to accept. And yet, at the same time, he wished to hear what Rick Hendrick had to offer.

The connection between Hendrick and Earnhardt Jr. had always been strong. As Hendrick recalled years later, when Junior was preparing to retire from the sport:

“I got to spend a good part of my life with a young man that I’ve become extremely close to. We have almost like a father/son relationship. Now I get to see him grow through all those stages of life, get a girlfriend, get married, and now be a father. The biggest regret I have is that he got hurt in the car.”

So, it was given that he didn’t immediately jump at Gibbs’ offer. However, Gibbs’ aggressive push to sign him had such a profound impact that Junior no longer wanted to look at the numbers.

“I went to see Rick, and he tried to give me a term sheet… I was like, ‘I don’t even want to see it. You and Kelly discuss the numbers, and y’all can handle it. I don’t even want to look at that. I don’t even want to know what you’re going to pay me.'” He further recalled.

“You’re going to pay me a lot of money that I probably don’t deserve. If it’s anything like what they pitched me at Joe Gibbs, it’ll be enough.”

The landmark deal that never went through

What about Richard Childress Racing, the team Dale Sr. made legendary in the No. 3? Junior confirmed in the same episode of his podcast that RCR was never a serious conversation.

“We never had a sit-down that I remember — we never had a real full sit-down pitch with Richard and the three.”

Beyond the lack of a formal meeting, Junior had already decided he was done with the No. 3. The number belonged to his father, and he wasn’t going to run it as a successor.

So, on June 13, 2007, Junior signed a five-year deal with Hendrick Motorsports. He never won a Cup championship there, and the early years were rough, with a 143-race winless streak and back-to-back finishes of 25th and 21st in points in 2009 and 2010. But he won 9 races, claimed a second Daytona 500 in 2014, and built something personal that no term sheet could have quantified.

He still wonders, though.

“I don’t regret it, but probably going to Gibbs,” he told Jeff Gluck of The Athletic in 2023. “I have no regrets over how all of that played out. But you cannot help but wonder, ‘What would it have been like had I went the other route?'”

What’s clear is that it wasn’t really a business decision. It was a gut call made by a 32-year-old who’d just lost his family team, felt sick looking at a number on a piece of paper, and chose the man who’d known his grandfather since they were teenagers in a small Virginia town.