Having dealt off a number of their own potential free agents at last month's trade (Brandon Workman, Kevin Pillar, Josh Osich), the Red Sox, other than Jackie Bradley Jr., don't have a lot of internal contractual decisions.
Beyond Bradley, they have to decide whether to exercise the 2021 option for starter Martin Perez - itself, pretty much a no-brainer given Perez's performance (4.33 ERA, 109 ERA+ ) and the relative affordability of the option ($6.25 million).
But if the Red Sox are smart, they would be wise to head off (or least forestall) a free agent issue down the road.
For now, Rafael Devers is under control for the next three seasons. This winter will represent his first year of arbitration eligibility, so his salary is bound to increase significantly from the current $692,500.
Now would be a good time to approach Devers with a multi-year offer that can only buy out his three remaining salary arbitration years, but also some free agency seasons, too.
And if you think that it's premature to start worrying about a player who's not eligible for free agency until after 2023, let me remind you of the curious case of one Marcus Lynn "Mookie'' Betts.
The Red Sox made some overtures to Betts long before he got within striking distance of free agency. Their first, which came when Betts had relatively the same amount of service time as Devers has currently, was for $100 million over five seasons. Betts and his representatives rejected the offer without much back-and-forth
A year later, they tried again, and again, the proposal was summarily dismissed.
By the time they got to the final off-season, Betts was close enough to the free agent finish line that it was useless for the Sox to try again. Months later, he was traded to the Dodgers, with the Red Sox increasingly convinced that he was going to test the market and worried that they would little more than a draft pick for him in return.
Now is when the Sox should be taking steps that the exact same scenario doesn't take place again with Devers.