Fans, media, and even some within the garage were blindsided by news of RFK Racing co-owner Brad Keselowski exiting the organization at the end of this year. This is his fifth consecutive year with RFK Racing, and he was seen as the clear successor to Jack Roush to lead the historic team.
Keselowski left behind a comfortable career at Team Penske, where he spent 12 consecutive years before leaving it all behind for a driver/owner role at Roush. That decision after the 2021 season was one of the more surprising driver moves in recent history, but what are the most unexpected changes to long-term and successful driver/team relationships in the garage?
Beyond Keselowski’s own surprising career trajectory, here’s five other unexpected driver and team breakups from the 21st century of NASCAR Cup Series racing, and be sure to let us know yours:
1. Dale Jr. leaves Dale Earnhardt Inc. after eight seasons
Dale Earnhardt Jr.
Photo by: Motorsport.com / ASP Inc.
The undisputed No. 1, as there was a time when no one thought Dale Earnhardt Jr. would drive for any team but DEI in his NASCAR career. His father built the race team and Dale Jr. drove that iconic red Budweiser No. 8 from his Cup debut in 1999 through the 2007 season. 17 of Dale Jr.’s 26 career Cup wins came while driving for DEI, including a six-win season in 2004.
Unfortunately, there was a lot of conflict within the team and relationships soured between several key individuals, including Dale and his stepmother, Teresa Earnhardt, who was the majority owner after Dale Sr.’s death. Among other internal issues, Dale Jr. wanted an ownership stake in his father’s Cup team but she refused, and he ultimately left for Hendrick Motorsports where he would remain for the rest of his career.
2. Kyle Busch leaves Joe Gibbs Racing after 15 seasons
Kyle Busch, Joe Gibbs Racing Toyota
Photo by: Rusty Jarrett via Getty Images
Busch joined JGR in 2008 and remained with the team through 2022, earning 54 of his 63 career Cup wins in the No. 18 Toyota. It was the ride that defined his legendary NASCAR career, and where he won both of his Cup Series titles in 2015 and 2019.
Most people, including Busch himself, thought he would end his NASCAR career at JGR. However, that simply wasn’t the case. As primary sponsor M&M’s announced that they would not return the following year, Busch was in the middle of contract negotiations. To put it simply, an agreement could not be reached on terms and Busch left JGR after 15 seasons. He was replaced by Ty Gibbs and the door number was changed to the No. 54, while Busch competed for Richard Childress Racing until his tragic passing in May of 2026.
3. Kevin Harvick leaves Richard Childress Racing after 13 seasons
Race winner Kevin Harvick, Richard Childress Racing Chevrolet
Photo by: General Motors
Harvick burst onto the NASCAR scene in 2001 under unimaginable circumstances. When Dale Earnhardt died on the last lap of the 2001 Daytona 500, RCR made the difficult decision to carry on. The black No. 3 became the white No. 29, and Harvick was given the difficult task of climbing into that race car. And yet, in just his third start, Harvick won at Atlanta in a photo finish that left everyone at RCR in tears. Harvick remained with RCR through the 2013 season, earning 23 of his 60 Cup victories with the team. Only Earnhardt himself won more Cup races while driving for Childress.
Harvick decided to seek a new opportunity with close friend Tony Stewart at Stewart-Haas Racing in 2014, but after he announced his planned departure, things quickly soured at RCR. He even got into it with Ty Dillon (grandson of Richard Childress) in a Martinsville Truck race near the end of his tenure, infamously saying: “That’s exactly the reason I’m leaving RCR because you’ve got those punk-ass kids coming up. They’ve got no respect for what they do in this sport and they’ve had everything fed to them with a spoon.” Harvick and Childress later reconciled, but the move did work out for Harvick as he became a champion in his very first year with SHR, ultimately ending his career there.
4. Tony Stewart leaves Joe Gibbs Racing after ten seasons
Tony Stewart poses with for Joe Gibbs Racing team members for his last race with the team after a ten year relationship
Photo by: Motorsport.com / ASP Inc.
After becoming an IndyCar champion, Stewart joined JGR and went NASCAR Cup racing in 1999. He stayed at Gibbs through the 2008 season, winning championships in 2002 and 2005. Stewart won 49 Cup races in his career, and 33 of those were as a JGR driver.
But despite spending his entire Cup career up to that point with Coach Gibbs, Stewart wanted to be a team owner, and had a great opportunity to do just that in absorbing the existing operation of Gene Haas. He also had reservations about JGR’s switch to Toyota due to his deep connections to GM, dating back to his open-wheel years It was quite a shock to see him leave such a successful career at JGR to form an unproven team. However, things worked out for Smoke, as he rapidly built it into a powerhouse team. He earned his third driver’s title in 2011, another as an owner in 2014, and SHR kept won dozens of races before it shut down after the 2024 season.
5. Matt Kenseth (13 seasons) and Carl Edwards (10 seasons) leave Roush
Jack Roush poses with his drivers, Matt Kenseth, Ricky Stenhouse Jr., Carl Edwards, Trevor Bayne and Greg Biffle
Photo by: Action Sports Photography
We’ve paired these two together as the situations were similar to one another. Kenseth and Edwards both started their Cup careers at Roush and were intensely loyal for quite some time. They both found great there success as well. Kenseth began his full-time Cup career in 2000, and earned 24 of his 39 career wins at Roush, ultimately leaving after the 2012 season. He earned the team its first Cup title in 2003, which was the last under a full-season championship format. Edwards was in contention for the title in his first full-time season in 2005, and nearly won it again in 2008 where he enjoyed an extraordinary nine-win season. 23 of his 28 career wins came as a Roush driver, but he left as well after 2014.
Kenseth and Edwards left Roush for similar reasons, and ended up in the same place — Joe Gibbs Racing. Roush was once one of the strongest in the Cup Series, but it was on the decline and downsizing. Jack Roush joked that Kenseth was “moving to the dark side” by joining the rival Toyota-powered team, and was surprised by his departure. By the time Edwards left, it wasn’t nearly as surprising, as Roush continued to struggle for pace. However, even a move to JGR wasn’t enough for Edwards to finally snag that elusive championship, and he shockingly walked away from competing after a dramatic and heartbreaking title loss in the 2016 finale.
BONUS: Brad Keselowski’s surprising exit from Team Penske and shock split from RFK
Brad Keselowski and Jack Roush, RFK Racing
Photo by: Jeff Robinson/Icon Sportswire via Getty Images
Keselowski’s own career trajectory has been full of surprises. He began his career set on a path to be the next Hendrick Motorsports driver, but with no open ride in 2010, he left the Chevy pipeline for Penske. He remained with Penske through the 2021 season, winning the 2012 championship — Penske’s very first Cup title. 35 of his 36 career wins came as a driver for Team Penske.
However, Keselowski had aspirations of team ownership in Cup, and previously ran a successful team in the NASCAR Truck Series. With no way of that happening at Penske, he joined Roush-Fenway in 2022 as a driver and part-time, with the team rebranding into Roush Fenway Keselowski (RFK) Racing. The team definitely saw an uptick in performance, even as Keselowski only reached Victory Lane once himself at Darlington in 2022. However, just this week, many were stunned as it was announced that Keselowski would soon depart the team he co-owns, and there don’t appear to be many options for him in 2027. According to reports from The Athletic, Keselowski had a disagreement with the rest of the ownership group about the direction of team, and the lack of a charter for RFK’s No. 60 next year was another point of contention. As for what happens next, we have no idea, but it’s hard to believe that one of the most senior drivers in the sport faces such a predicament.Â
Watch: A closer look at Brad Keselowski’s departure from RFK Racing
Â
