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NASCAR 101: Top 5 Silly Season Moves of All Time

Unlike in most other sports, the term “free agency market” isn’t used in NASCAR. Instead, NASCAR begins “silly season” usually around the halfway mark of the year, and there are much more lame duck drivers and teams than in “stick and ball” sports.

There have still been some huge driver transactions in the near 70-year history of NASCAR. We’re looking at the top five silly season moves of all time, ranked on both impact on the sport and driver/team statistics following the move. Obviously, we’re looking at drivers with prior Cup Series experience; otherwise, this list would be littered with then-rookie drivers such as Jimmie Johnson and Jeff Gordon.

5. Kyle Busch to Joe Gibbs Racing (2008)

When Dale Earnhardt Jr. signed with Hendrick Motorsports in 2007, it became a pretty loaded team. It may seem like nothing now, but the idea of a team with Gordon, Johnson and Earnhardt all within the same facility was insanity at the time. Unfortunately, Hendrick had

Kyle Busch celebrates a victory at the Monster Energy All-Star Race, the first of his career, in 2017. (Photo: John Harrelson / NKP)

to make room for Earnhardt and couldn’t really get rid of Casey Mears in just the second year of his contract. Instead, Kyle Busch’s contract with the organization wasn’t extended, and he left for Joe Gibbs Racing.

Ten years later, it’s obvious that Busch’s move to Gibbs was the better move than Earnhardt to Hendrick.

Busch was already a good driver, winning four races in his first three seasons and finishing fifth in points in 2007. But in 2008 alone, he exploded and won eight races. Overall, Busch has won 34 Cup Series races, the 2015 championship, 77 XFINITY Series races, the 2009 XFINITY Series championship and 40 Camping World Truck Series races. When it comes to pure hardware, this move might just be the best in NASCAR history.

4. Darrell Waltrip to Junior Johnson & Associates (1981)

This pairing between loudmouth Darrell Waltrip and Junior Johnson dominated most of the early to mid-1980s. In six seasons, Waltrip won 43 races and three championships. Highlights include seven straight wins at Bristol Motor Speedway, back-to-back 12-win championship-winning seasons in 1981 and 1982 and six seasons in the top five in points.

Forget Kevin Harvick, Waltrip was the real closer.

In all three of his championship winning seasons, Waltrip came back in the last half of the season after a somewhat slow start. In the last 16 races of 1981 alone, he had 13 straight top fives, never finished outside the top 10 and won eight races. In 1985, Waltrip only finished out of the top 10 twice in the last 20 races, beating Bill Elliott in one of the most surprising points battles in NASCAR history. Elliott had the flashier season, winning the Winston Million with wins in the Daytona 500, Winston 500 at Talladega Superspeedway and the Southern 500. But Waltrip was just plain better than Elliott, especially in the last few months of the season.

All great pairings must come to an end, however, and it happened in 1987 when the two split. There were no real hard feelings, with Waltrip speaking highly of Johnson throughout his years as a broadcaster.

3. David Pearson to Wood Brothers Racing (1972)

David Pearson drove somewhat full-time in three seasons in the 1960s, winning three championships — one per year with the No. 21 team. But the grind was hard on Pearson, and with the fall of Holman-Moody in 1971, Pearson sought work as a part-time driver. The Wood Brothers routinely skipped the short track races on the schedule and save for Martinsville. The two were basically made for each other, the perfect pairing at the perfect time. In 143 races throughout the 1970s, Pearson won 43 races — or 30 percent of events he entered — and turned the Wood Brothers into a true marquee team.

Pearson still holds team records as the driver with the most wins in the organization, the most poles and the best points finish (third in 1974). His 1973 season in particular might just be the finest season in NASCAR history, with 11 wins and 14 top fives in 18 races. No driver has ever won that many races in as few starts as Pearson.

2. Cale Yarborough to Junior Johnson & Associates (1973)

No driver-team owner combination might have worked better than Cale Yarborough and Junior Johnson. Both were cut from the same cloth as drivers; drive hard every lap of every race. Yarborough won 55 races with Johnson in the 1970s and three straight championships from 1976 to 1978.

Save for 1975, when the team had to miss three races and Yarborough finished ninth in points, Yarborough never finished outside of the top four in points and outside of the top two only once. But after eight seasons, Yarborough decided to retire from full-time racing to focus on his family, leaving the ride open to rival Darrell Waltrip in 1981.

1. Tony Stewart to Stewart-Haas Racing (2009)

It seemed like Tony Stewart was never going to leave Joe Gibbs Racing, at least while he raced in NASCAR. Stewart won 33 races in ten seasons and two championships with the organization, after all. And with a team loaded with young talent in Denny Hamlin and Busch, Stewart was the cornerstone for the organization.

Then, Gene Haas called and offered Stewart half of his team.

In seven seasons of Cup competition, Haas CNC Racing had one top five and 14 top 10s. The two-car team’s best points finish was 28th in 2006 with Jeff Green. Such a small team wasn’t going to normally attract a superstar like Stewart to the fold.

But there was groundwork for greatness in the organization. Haas had a lot of money to spend, even after serving time in federal prison due to tax evasion. The team had a relationship with Hendrick Motorsports that was greatly expanded once Stewart entered the fold.

In one year, Haas drivers went from Scott Riggs and Tony Raines to new team co-owner Stewart, along with longtime friend and defending Daytona 500 champion Ryan Newman. In nine seasons of operations, the newly renamed Stewart-Haas Racing has expanded to four cars, won 38 races and has earned two championships, one with Stewart himself and one with Kevin Harvick.

Before this season, Forbes valued the team at $180 million- making this the largest move in free agency history from a monetary value. Stewart’s $90 million owned in team value is only behind top NFL quarterback contracts that reach above the $100 million mark.

But even outside of the money, this was the most impactful move in silly season history. This move turned a back running two-car team into a four-car powerhouse. Nothing Stewart-Haas Racing has done or will ever do would have been possible without this one move.

About the author

Michael has watched NASCAR for 20 years and regularly covered the sport from 2013-2021. He moved on to Formula 1, IndyCar, and SRX coverage for the site, while still putting a toe in the water from time-to-time back into the NASCAR pool.

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I think Richard Petty leaving Petty Enterprise for Mike Curb should have been top of the list…

Tim S.

Petty to Curb was a move that a lot of people *thought* would be a big deal, much like Earnhardt to Hendrick. Similar results. A couple of marquee victories and not a whole lot more.

And while Stewart-Haas is definitely a valuable team, I bet everyone involved made at least $90 million on all the folks switching over from #8 to #88 gear.


“Both were cut from the same cloth as drivers; drive hard every lap of every race.”

I don’t think any driver now could drive for Junior.


David Pearson won a lot of races with the Wood Brothers, but never a championship. He won the 1966 championship in the #6 Dodge owned by Cotton Owens, then he won the 1968 and 1969 championships in the #17 Ford owned by Holman and Moody.


The Dale Jr.-Kyle Busch move in 2007 turned out a win-win for both. Jr. got out from the crumbling of DEI and Kyle got to spread his wings with Gibbs. It was still a shocking move at the time considering Hendrick and Jeff Gordon/Jimmie Johnson were the biggest enemies of Jr. Nation. The next year after Kyle dumped Jr. at Richmond all of a sudden the boos for Gordon got softer and Kyle became public enemy No. 1.


Earnhardt to Childress should be here.
Weirdly, I think Harvick to Stewart-Haas would be a better choice than Stewart to Stewart-Haas. I think Harvick had more of a future to his career when he left Childress than Stewart did when he left Gibbs, and also Harvick leaving devastated Childress while Gibbs is still (in theory) strong despite the fluke of them not having won yet this year.

I think I would put Earnhardt in first place and might even leave Stewart off…

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