As the NASCAR Cup Series presses on after its first off week of the 2021 season, I decided to share another one of my bizarre (and likely erroneous) Silly Season predictions. As it was revealed late last season, the Wood Brothers have decided to boot fan-favorite Matt DiBenedetto from their famed 21 car in favor of the young, Penske backed xFinity champ, Austin Cindric. As soon as the announcement regarding DiBenedetto came out, speculation immediately began.
At first, it seemed like Brad Keselowski would depart from Team Penske in favor of the vacated ride at Hendrick Motorsports thanks to the departure of 7-time champion, Jimmie Johnson. From there, it seemed obvious that either DiBenedetto or Cindirc would get the newly vacated no. 2 car at Penske, and the other would get the 21. However, Brad Keselowski re-signed with Penske on a one year contract extension and is still expected to part with the team after over 10 years.

I don’t think the Wood Bros. intend to change their plans with Cindric/Penske and send him over to the 2, nor do I think DiBenedetto will go there either. However, I do believe Matty D is staying within the Ford organization. Before we take a gander at his options and where I think he’ll end up, we should look back on his career up until this point.
DiBenedetto burst on the Cup scene in 2015, running 33/36 races for the now defunct BK Racing. He had zero poles and a best finish of 18th at Talladega in April. 2016 only got better from there. He ran 35/36 races and scored his first career top ten at Bristol in the spring, where he finished sixth. For the 2017 season, DiBenedetto moved from BK Racing to GoFas Racing. For the first time, DiBenedetto completed all 36 races, and scored two more top tens. He stayed at GoFas for 2018 and got another top ten. DiBenedetto’s big break came in 2019 when he signed with Joe Gibbs Racing affiliate Leavine Family Racing. Right away DiBenedetto began making a statement. He led a bunch of laps in the Daytona 500 before getting caught up in a wreck. Later that season, DiBenedetto set a career best finish of fourth at Sonoma. Further into the season, DiBenedetto was eyeing a first win at Bristol, but after late contact with a lapped car, he settled for his best finish to date of second. In 2020, Matt was replaced in the 95 with Christopher Bell. DiBenedetto found a home at the famous Wood Brothers Racing team. He tied his top five count from the previous season with 3, but got 4 additional top tens in 2020. However, this glorious run came to an abrupt halt. At the end of 2020, DiBenedetto was informed that although he’d be back in 2021, he would need to find a new home in 2022 as rising star Austin Cindric would be piloting the 21 in ‘22.

DiBenedetto is still young, and has a fairly large fanbase, so it shouldn’t be too hard to find a ride…right? Well, not a whole lot of top rides are open. Hendrick seems like they’ll keep their four drivers, as will Gibbs and Stewart-Haas. I doubt DiBenedetto will switch to the Penske 2 car, nor do I think Penske will send DiBenedetto to their xFinity team. I do believe, however, that Matt DiBenedetto will stay within the Ford camp. Where will this ride come from though? Like I already mentioned, Penske and SHR are likely off the table. I don’t think Matt D will drop to Front Row Racing, Live Fast Motorsports, or Rick Ware Racing either. Which leaves one. Roush.
Roush (Fenway) Racing has been a prominent team in the NASCAR Cup Series garage for over 30 years. From the single car operation with Mark Martin, to the Dream Team of Matt Kenseth, Kurt Busch, Greg Biffle, Mark Martin, and Carl Edwards, Roush has been a staple of NASCAR competition for ages. Lately, however, they’ve fallen off. After Matt Kenseth and Carl Edwards departed the team in favor of Joe Gibbs Racing, they have only won two races, both in 2017 with Ricky Stenhouse, Jr. Currently, the team fields two cars, the 6 with Ryan Newman and the 17 with Chris Buescher. As bad as these past few seasons have been, there does seem to be light at the end of the tunnel. Newman scored a top five at Bristol and Buescher scored a stage win at Homestead. And these haven’t necessarily been flukes either. Both Newman and Buescher have been constant top 15 threats each week. So what does this have to do with Matt DiBenedetto?

The two drivers at Roush vary in age. Here, you have young 28 year old Chris Buescher, full of talent and with plenty of time left in NASCAR. Ryan Newman, however, has been in the NASCAR Cup Series since 2002. Newman is 43 years old and has 18 wins, his most recent coming at Phoenix in 2017. After a horrifying, near-fatal crash at the end of the 2020 Daytona 500, many people thought he would retire at the end of the season. However, he signed on another year with Roush, but I think this is his last. I’m expecting Newman to announce his retirement soon, followed by the announcement that Matt DiBenedetto will pilot the Roush no. 6 for 2022. With two young stars, I believe Roush is in a rebuild phase; especially if Buescher runs as well as he has so far this season.
Where do you think Matt DiBenedetto will end up? Will Newman really retire? Let me know on Twitter or leave a comment on this article. Also, check out my other Silly Season ‘22 article here!