Betts, who turned 27 last October, has said several times over the past few seasons that he will see what the free agency market can offer after the 2020 season.
In March 2019, Betts said: "I love it here. This is a great place to be, to spend your career here. That doesn't mean you sell yourself short." Last July, he said: "I love the front office, my teammates, coaches. Everybody. It's been nothing but amazing here. Just because you go to free agency doesn't mean you don't want to be somewhere. It's just a part of the business."
If the Red Sox want Mookie Betts to be wearing a Red Sox uniform in 2021 (and beyond), they will have to compete with the other 29 teams and sign him over next winter. Jen McCaffrey of The Athletic wonders about the likelihood of that scenario — with the possibility of the Red Sox reducing payroll for 2021 and beyond:
[A] free agent returning to his original team isn't all that common ...One commenter, Kevin D., questions McCaffrey's use of active WAR leaders (with hints of mansplaining), adding:
Among the top 100 active leaders in WAR, there's just one example that comes close. Jose Abreu of the Chicago White Sox, who re-signed this offseason in Chicago after reaching free agency, is the only player in that group to have reached free agency for the first time and then re-sign with the team with which he spent his entire career — without previously having agreed to a contract extension with that team.
And Abreu is not even a great Betts comparison, for several reasons: His age (Abreu turns 33 at the end of the month) and the fact he began his career as an international free agent with the White Sox. As a drafted player, Betts hasn't had that kind of leverage in contract negotiations outside of a few million dollars in arbitration.
In other words, Betts entering free agency for the first time and re-signing with his original team without ever having signed an extension would be unprecedented among current players of his caliber over the last decade, when contracts ballooned into the $300 million range.
While there's no template for Betts re-signing in Boston after the 2020 season, there are still a handful of players who loosely fit that mold.
Arenado is one who signed an extension entering his final year. In fact, shortly after he set the arbitration record for highest salary to a final-year arbitration player at $26 million, he signed an eight-year, $260 million deal with the Rockies. It doesn't seem like Betts is trending in the extension direction, but he does find himself in a similar spot to Arenado at this time last year.
Stephen Strasburg is another close-but-not-quite fit. The 31-year-old signed a seven-year, $245 million deal to remain with the Nationals this past winter, the team he'd been with his entire career. Though it was technically his first time in free agency, Strasburg had already signed an extension with the Nationals in 2016 for seven years, $175 million that included an opt-out after 2019. The opt-out allowed him to remain with the Nationals but also to demand a higher price. If Betts does want to return to Boston, he'll likely force the Red Sox to outbid others on the open market.
Players like CC Sabathia and Adam Wainwright hit free agency multiple times and re-signed with their previous teams in New York and St. Louis, but those deals were signed well after their first forays into free agency when they'd already earned hundreds of millions of dollars. Similarly, Alex Gordon remained with the Royals after hitting free agency in 2018, but he had already signed two different contract extensions.
[T]he Red Sox will have a $27.7M advantage from an incremental payroll standpoint. Thus, $10M additional revenue for Boston gets Mookie to $37.7M a year. EVERY OTHER TEAM will need to add the full $37.7M. Not that many teams can afford it and the ones that can may have to pursue him in lieu of a current superstar on their team (NYY-Judge and Sanchez, LA-Bellinger, Buehler, Muncy etc.). This reduces the chances significantly that a bid will come in that far surpasses the Red Sox bid from a team that is as competitive as the Red Sox. ... If the Red Sox want him, all they need to do is make a fair market bid for him.I get what he's saying about Boston's advantage, but every other team is already paying for a right fielder, so none of them would need to "add the full $37.7M" (or whatever Betts's AAV will be) as extra revenue.
The Red Sox have plenty of money to pay Betts a fair market salary (discussions of the team's desire to incur additional salary cap penalties are another story) and I'd like to think that if the various piles of money on the table next winter are the same, Mookie will choose the Red Sox's pile.
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