NASCAR Cup Series: 3 possible Team Penske drivers for 2021

LAS VEGAS, NEVADA - FEBRUARY 21: Brad Keselowski, driver of the #2 Discount Tire Ford, drives during practice for the NASCAR Cup Series at Las Vegas Motor Speedway on February 21, 2020 in Las Vegas, Nevada. (Photo by Jonathan Ferrey/Getty Images)
LAS VEGAS, NEVADA - FEBRUARY 21: Brad Keselowski, driver of the #2 Discount Tire Ford, drives during practice for the NASCAR Cup Series at Las Vegas Motor Speedway on February 21, 2020 in Las Vegas, Nevada. (Photo by Jonathan Ferrey/Getty Images) /
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DAYTONA BEACH, FLORIDA – FEBRUARY 12: Matt DiBenedetto, driver of the #21 Motorcraft/Quick Lane Ford (Photo by Jared C. Tilton/Getty Images)
DAYTONA BEACH, FLORIDA – FEBRUARY 12: Matt DiBenedetto, driver of the #21 Motorcraft/Quick Lane Ford (Photo by Jared C. Tilton/Getty Images) /

Matt DiBenedetto

If Brad Keselowski leaves Team Penske and Team Penske do not promote Austin Cindric to their NASCAR Cup Series team right away, this would open the door for Matt DiBenedetto to have his best career opportunity yet.

DiBenedetto signed with Wood Brothers Racing after Paul Menard made the unexpected decision to retire after the 2019 season, a decision he announced in September. He told the team to sign DiBenedetto, who was slated to be replaced by Christopher Bell at the Joe Gibbs Racing-affiliated Leavine Family Racing.

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The 28-year-old Grass Valley, California native has made the most of his opportunities thus far in the Cup Series, even though he is now with his third team in three years. With his current opportunity as the driver of the #21 Ford definitely being his best one yet, he still has a lot to prove before Team Penske think about giving him a ride alongside Joey Logano and Ryan Blaney.

But if Keselowski leaves and DiBenedetto does well enough in 2020, signing DiBenedetto could also give Team Penske the additional flexibility to either keep Cindric in the Xfinity Series or allow him to do what Blaney did at Wood Brothers Racing in the hope of landing an opportunity with Roger Penske’s team in the future.

DiBenedetto is far more experienced than a young driver such as Cindric and has proven what he can do when given the right opportunity during his time at some of the smaller teams.

More of the same in 2020 would bode very well for him and put him in a position that he has never been in before, one that includes ride security with, at the very least, a decent team for the coming year.

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When the 2021 NASCAR Cup Series season rolls around, will Team Penske’s lineup look like it does now with Brad Keselowski alongside Joey Logano and Ryan Blaney, or will Keselowski leave for Hendrick Motorsports and be replaced? If he is replaced, would he be replaced by Austin Cindric, Matt DiBenedetto or somebody else? It’s only March, but Silly Season is already starting to heat up thanks to Blaney signing his extension with the Captain’s team.