
The 2021 NASCAR Cup Series free agent class is one of the most loaded in quite some time. Who are the top five pending free agents in this class?
There are a few differences in the NASCAR Cup Series driver lineup from the 2019 season to the 2020 season, but among the top-tier teams, there is really only one big change.
The lineups of Hendrick Motorsports (four drivers), Joe Gibbs Racing (four drivers), Team Penske (three drivers) and Chip Ganassi Racing (two drivers) are all the same.
However, Stewart-Haas Racing, for the fourth consecutive season, made a change. Cole Custer is the replacement for Daniel Suarez behind the wheel of the #41 Ford at the four-car Ford team.
Elsewhere throughout the field, Chris Buescher moved from JTG Daugherty Racing to Roush Fenway Racing to replace Ricky Stenhouse Jr. behind the wheel of the #17 Ford and Stenhouse replaced Buescher behind the wheel of the #37 Chevrolet.
Additionally, Christopher Bell moved from the Joe Gibbs Racing Xfinity Series team to the Joe Gibbs Racing-affiliated Leavine Family Racing to replace Matt DiBenedetto behind the wheel of the #95 Toyota while DiBenedetto replaced the retiring Paul Menard at Wood Brothers Racing behind the wheel of the #21 Ford.
But on paper, this may not even come close to measuring up to what the changes from the 2020 season to the 2021 season could be, as the free agent class after the upcoming year is absolutely loaded.
Following Team Penske’s confirmation of Ryan Blaney on another multi-year deal, here are the top five pending free agents in this stacked class.

5. Matt DiBenedetto
Matt DiBenedetto constantly finds himself as a pending free agent in the NASCAR Cup Series, sometimes by his own doing and sometimes via circumstances that are out of his control. His status as a free agent following the 2020 season, however, is unlike what it was before.
After spending two seasons with BK Racing in 2015 and 2016, he made the move to Go Fas Racing ahead of the 2017 season. He could have returned to the team for a third year in 2019, but he opted to take a gamble and leave the team, seeking a better ride. He finished in 32nd and 29th place in the 2018 and 2019 championship standings, respectively, so the move made sense.
He landed with the Joe Gibbs Racing-affiliated Leavine Family Racing, but that ride had all the makings of a one-year rental from the start, with Christopher Bell looming at Joe Gibbs’s Xfinity Series team. Sure enough, despite a dramatic increase in his and the team’s performance throughout the 2019 season, Leavine Family Racing opted to replace him with Bell.
Paul Menard made the unexpected decision to retire after the 2019 season, and before he did, he told Wood Brothers Racing that DiBenedetto should replace him behind the wheel of the #21 Ford, and that’s how the 28-year-old Grass Valley, California native got to where he is now.
DiBenedetto is with the team on a one-year deal, but he should have no shortage of possibilities for 2021 given how he has performed. He has already been talked about as a possibility to replace retiring seven-time champion Jimmie Johnson at Hendrick Motorsports, although several other drivers have been discussed as well.
Team Penske have a technical alliance with Wood Brothers Racing. Having recently re-signed Ryan Blaney through at least the 2022 season and having already signed Joey Logano through at least the 2023 season, all eyes will be on Brad Keselowski, who has also been rumored to Hendrick Motorsports.
If Keselowski leaves Team Penske, would the team hire DiBenedetto or opt for Xfinity Series driver Austin Cindric?
Regardless, this Silly Season will probably end up being even more interesting than past Silly Seasons for DiBenedetto because it shouldn’t be a matter of whether or not he gets a ride, but where he gets a ride.

4. Erik Jones
The 2020 season is Erik Jones’s third full season driving for Joe Gibbs Racing after replacing Matt Kenseth behind the wheel of the #20 Toyota ahead of the 2018 season.
There was speculation that Jones would not be back with the team in 2020 with Christopher Bell available and Jones being so hot and cold, but Joe Gibbs Racing opted to retain the 23-year-old Byron, Michigan native.
However, they only extended his contract by one year, making him a pending free agent after 2020.
Jones is the only Joe Gibbs Racing driver not under contract through the 2021 season, but two of their drivers are nearing 40. It’s hard to not see the team wanting to retain him for their long-term future given his age, potential and upside, which he has shown on multiple occasions; only five drivers finished the 2019 season with more top four finishes than he did.
With that being said, with Bell now in the Cup Series and in a prime position to replace Jones in 2021 if their respective performances warrant it, that would leave Jones looking for a ride, and with several seats potential available. There is no doubt that he is on the hot seat.
Bell doesn’t have the Cup Series experience that Jones has, but believe it or not, he is actually roughly a year and a half older than Jones is.
One of the reasons why Bell was promoted to the Cup Series with Leavine Family Racing is believed to be that Joe Gibbs Racing didn’t want to risk him getting away from the organization due to the team being full for an extended period of time. A promotion for the 2021 season would likely leave Jones looking for a new ride.

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.

2. Alex Bowman
The 2020 season is Alex Bowman’s third full season driving for Hendrick Motorsports after replacing Dale Earnhardt Jr. behind the wheel of the #88 Chevrolet ahead of the 2018 season, and it is a contract year for him after signing a two-year contract extension in the middle of 2018.
All signs point toward Hendrick Motorsports retaining Bowman in the 2021. The team have several sponsorship deals lined up for the #88 Chevrolet past the 2020 season, and Bowman has shown potential and improvement in his first two-plus seasons driving for the team. After winning one race in his first two seasons, he is already a winner in 2020.
Plus, Jimmie Johnson is set to retire after the 2020 season, meaning they will already have to worry about replacing one driver. Even with William Byron and Chase Elliott already under contract through at least 2021 (Byron undisclosed, Elliott through 2022), it makes more sense to stick with Bowman and retain three drivers as opposed to just two.
But if they opt not to, the strides that the 26-year-old Phoenix, Arizona native has shown would make him a target for several other teams. He still struggles a bit with inconsistency, but two round of 12 appearances in his first two full seasons driving for Hendrick Motorsports bode well for him.
Additionally, after becoming the first driver in Cup Series history to finish in second place in three consecutive races without a career victory, he responded only five races later by driving to victory lane, and he did it in the face of adversity, blowing a lead late and battling back. If he ends up hitting the market, he won’t be there for long.

1. Kyle Larson
It’s no secret that Kyle Larson’s 2021 plans are up in the air. For that reason, there has been a ton of speculation about his future, and justifiably so considering the fact that he will be in high demand after the 2020 season ends, assuming he doesn’t sign a new contract before then.
Larson’s name has already been thrown around as a potential replacement for one of the current drivers at Stewart-Haas Racing, the potential replacement for Jimmie Johnson at Hendrick Motorsports, and a potential long-term option for Chip Ganassi Racing, where he has spent his entire full-time career in the Cup Series thus far.
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The 27-year-old Elk Grove, California native has maintained that his next contract will revolve around whether or not he is allowed to continue running the dirt track racing schedule that he runs when not behind the wheel of a Cup car, and he has stated in the past that he would like to be able to try other forms of racing as well, most notably IndyCar in the Indianapolis 500.
Larson had gained the reputation of somewhat of a choker in recent years, as he finished runner-up on multiple occasions after blowing late leads in races during his two-plus-year win drought that began during his career year in 2017. But he finally ended what was a 75-race win drought by winning at Dover International Speedway in early October of 2019.
Even though he has won just one race in the last two-plus years, he is in the midst of a four-year stretch of top nine finishes in the championship standings, and he finished in a career-high sixth place in 2019 after advancing to the round of 8 for the first time in his career, even with only one win.
His career-high four wins in the 2017 season showed what he is capable of accomplishing when he isn’t blowing leads and experiencing other setbacks. That upside coupled with the fact that he is still only 27 years old make him the top pending free agent after the 2020 season.
Other notable pending free agents after the 2020 NASCAR Cup Series season include but are not limited to Aric Almirola and Clint Bowyer at Stewart-Haas Racing and Matt DiBenedetto at Wood Brothers Racing. Where will all of these drivers end up when the 2021 season rolls around?

