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Truckin’ Thursdays: The Matt DiBenedetto-Rackley Split is Odd

On Aug. 30, Matt DiBenedetto announced that he would depart from Rackley-Willie Allen Racing (commonly known as Rackley W.A.R.) at the end of the 2023 NASCAR Craftsman Truck Series season.

DiBenedetto has spent the last two seasons with the team, in which he notched his and the team’s first career Craftsman Truck Series win at Talladega Superspeedway in October 2022, and built on that momentum in 2023, as the team is currently in the midst of its very first playoff run.

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The announcement is quite a surprise for several reasons. DiBenedetto joined Rackley WAR after spending several seasons in the top echelon of NASCAR, the Cup Series, driving for BK Racing, Go Fas Racing, Leavine Family Racing and Wood Brothers Racing. His never-say-die attitude and stellar finishes with underfunded teams (three of which do not exist today) won over the hearts of many.

But a win was something DiBenedetto just couldn’t achieve, and after the 2021 season, DiBenedetto decided to take a step back and return to lower series racing to try to re-prove himself. In his two-year tenure with Rackley, DiBenedetto looked happier than he was in recent years in the Cup Series. His continued failure to produce wins despite his Cup Series success was taking a mental toll on him.

But then Rackley took a chance on DiBenedetto, signing him as its full-time driver after going through a rotation of drivers in 2021, including team owner Willie Allen, following the release of original full-time driver Timothy Peters. While 2022 wasn’t exactly an unforgettable year, the Talladega win launched them into what has been a remarkable 2023 season for the team’s standards.

Furthermore, DiBenedetto very much felt at home with Rackley, referring to the family-like atmosphere of the team. On multiple occasions, DiBenedetto called the move to Rackley a great decision, and has said how much he feels at home with the team based out of Centerville, Tenn. He also told Frontstretch that his quality of life had improved by joining the team.

So why leave?

What seems most baffling about the decision is DiBenedetto seemingly doesn’t have anything lined up after this season. With Rackley WAR arguably on the rise in the Truck Series, and with playoffs being the main focus right now, one might question why now was the time for DiBenedetto to not only leave the team, but also announce it in the midst of a playoff run. And its certainly worth questioning why one would leave a team with nothing allegedly lined up.

I guess the overarching question is, where do both parties go from here?

With the sudden announcement, both parties now have some work to do to compete in 2024. Though I feel like it will be easier for Rackley WAR to find another driver than it will be for DiBenedetto to find a team to compete with.

Since entering the Truck Series, Rackley WAR has never been in the business of picking up a rookie for its full-time ride. Before moving to a rotation of drivers, Peters, the original full-time driver, had 11 wins in the Truck Series with the now-defunct Red Horse Racing and soon-to-be-defunct GMS Racing, and was in the sport for 15 years at that point.

Even the drivers the team tabbed to fill in throughout had been in the sport for a while at that point. Josh Berry was in the midst of a part-time Xfinity Series season split between JR Motorsports and Jordan Anderson Racing. Brett Moffitt had been in competing in NASCAR since 2011 at that point, and team owner Allen made a handful of NASCAR starts in the late 2000s.

Even its second truck featured drivers with years of experience at that point. William Byron drove the No. 27 in the team’s home race at Nashville Superspeedway in 2021, and was already an Xfinity champion and Cup regular. Tate Fogleman attempted three races in the No. 26 in 2022, making one at Pocono Raceway. Fogleman had just upset the field at Talladega in 2021 with Young’s Motorsports notching his first career win and was a Truck Series regular since 2020.

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Then there’s DiBenedetto, who has spent almost as many years as Peters and Allen in the sport with several different teams. So should Rackley WAR go after a veteran again? Before last week, I would have said no.

But now Grant Enfinger is on the table, and I believe that would be a good pairing.

With the shutdown of GMS Racing at the end of the season, Enfinger does not have a ride for 2024. Rackley WAR could be a perfect home for him, as the veteran approach the team has taken, combined with its rise to prominence this season, could allow Enfinger to continue performing at his best in the Truck Series.

As for DiBenedetto, there are a couple options. Of course, there’s the vacant JR Motorsports No. 8 that Berry is leaving behind at the end of the season in the Xfinity Series. Or maybe another top-tier Truck Series ride for him, such as Zane Smith’s No. 38 or Carson Hocevar’s No. 42 that he could slide into for next season.

But my bet would be on Kaulig Racing’s vacant Cup Series ride that Justin Haley will leave behind following this season.

Kaulig team president Chris Rice told SiriusXM NASCAR that people would be surprised at what the team will do with the No. 31 car, and putting DiBenedetto in the car certainly would be a surprise. But DiBenedetto will likely need sponsorship for wherever he will go, as Rackley Roofing has sponsored almost every race he’s competed in, and that’s just because Rackley Roofing is 50% owner of Rackley-WAR.

But the DiBenedetto-Rackley split is just another piece of the 2024 silly season puzzle that has opened up, and it will be interesting to see how both parties respond to it in 2024.

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Anthony Damcott joined Frontstretch in March 2022. Currently, he is an editor and co-authors Fire on Fridays (Fridays); he is also the primary Truck Series reporter/writer and serves as an at-track reporter. He has also assisted with short track content and social media, among other duties he takes/has taken on for the site. In 2025, he became an official member of the National Motorsports Press Association. A proud West Virginia Wesleyan College alum from Akron, Ohio, Anthony is now a grad student. He is a theatre actor and fight coordinator in his free time.

You can keep up with Anthony by following @AnthonyDamcott on X.

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