NASCAR Cup Series: Top 5 pending free agents for 2021

Brad Keselowski, Team Penske, and Kyle Larson, Chip Ganassi Racing, NASCAR (Photo by Brian Lawdermilk/Getty Images)
Brad Keselowski, Team Penske, and Kyle Larson, Chip Ganassi Racing, NASCAR (Photo by Brian Lawdermilk/Getty Images) /
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Brad Keselowski, Team Penske, NASCAR (Photo by Chris Graythen/Getty Images) /

3. Brad Keselowski

Brad Keselowski is in his 11th consecutive full season driving for Team Penske in the Cup Series, and the 2020 season is a contract year for him after signing a multi-year extension to continue driving the #2 Ford back in July of 2017.

Throughout his career as a full-time Cup Series, the 36-year-old Rochester Hills, Michigan native has only ever driven for Team Penske. But with him having failed to get out of the round of 12 for two consecutive seasons and with current Xfinity Series Austin Cindric available in the midst of the youth movement, could Team Penske look elsewhere?

Perhaps even Matt DiBenedetto, who took over for the retired Paul Menard at the Team Penske-affiliated Wood Brothers Racing, would be promoted to the team.

It’s not out of the question; they already have veteran Joey Logano under contract through the 2023 season and they recently extended Ryan Blaney’s contract through at least 2022, so it wouldn’t be like they would be completely overhauling their lineup.

With that being said, Keselowski still has what it takes to win races on a regular basis, having won at least three in each of the last four seasons and a total of 13 during that four-year span, so it would come as somewhat as a surprise if Team Penske cut him for somebody else, really anybody else, at this point.

But perhaps Keselowski wants to move on, and if he does, there are certainly other teams that would jump at the chance to sign the 2012 champion, and he has made note of that.

Keselowski drove for JR Motorsports in the Xfinity Series in the 2008 and 2009 seasons, and he drove for Hendrick Motorsports in select races in the 2008 and 2009 Cup Series seasons. The only reason he ended up at Team Penske in Cup is because Hendrick Motorsports had no room for him; the door has seemingly remained open for a return in the meantime.

With one if not two seats open at Hendrick Motorsports after the 2020 season, this could be the perfect opportunity for Keselowski to finally drive for Rick Hendrick’s team if Roger Penske lets him go and/or Keselowski decides that it is time to move on.