Even before the Red Sox turn their attention to the free-agent market or trade talks this winter, the two biggest items on their offseason to-do list are getting contract extensions finalized with the left side of their own infield: third baseman Rafael Devers and shortstop Xander Bogaerts.
Here's what we know about those efforts to date, based on conversations with multiple industry sources:
* Assistant general manager Eddie Romero met with Devers earlier in the week in the Dominican. Romero was not in the D.R. expressly to visit Devers; rather, he oversees much of the team's international signings, and the Dominican is an area rife with young talent.
It's clear that the Red Sox are intent on keeping the lines of communication open with Devers throughout the offseason, though this time of year is hardly a typical time frame for a future extension. Ordinarily, players who are still under team control -- as Devers is through the 2023 season -- are approached about extensions after the first of the year, when much of an organization's roster-building is complete and there's time to pay attention to more long-term goals.
It's unclear whether the Red Sox provided an updated offer from the one they presented last spring. That March 2022 proposal was said to be nowhere market value and had the effect of alienating Devers.
Romero and Devers have a history that dates back a decade, when Devers signed as a 16-year-old. Devers trusts Romero and it only makes sense that the Sox chose Romero as their emissary to open the lines of communication for what will be an important offseason.
* While the Red Sox are intent on extending Devers, there is a far greater sense of urgency surrounding Bogaerts' contractual status. Bogaerts is universally expected to opt out of his current deal with the Red Sox within days of the completion of the World Series.
In the final weeks of the 2022 regular season, Red Sox ownership met in person with Bogaerts to convey their interest in retaining him. According to a baseball source, that outreach has continued throughout the past month.
For the time being, the Red Sox enjoy a period of exclusivity with Bogaerts -- until he officially opts out of his contract, the Red Sox are the only team with whom had can have negotiations.
The Red Sox are very much aware of the significance of that window and their preference would be to get something done with Bogaerts before other clubs have an opportunity to make their own offers.
But a source familiar with the talks noted that, given how close Bogaerts is to becoming a free agent, a preemptive deal, while not impossible, is regarded as a long shot. If Bogaerts gets to the point where he can and will opt out, that won't signal an end for the Red Sox' pursuit of him. But it undoubtedly will cost them more money.
* When it comes to Bogaerts, it's always wise to consider The Boras Factor.
Agent Scott Boras is known to advise clients to get to the open market, where they can expect to receive bids from multiple teams. It's a rule of supply and demand: the more teams interested in a player, the better chance there is of driving up the asking price.
In 2019, when Bogaerts signed his current deal (six years, $120 million with this year's opt-out), it was decidedly below market value. But Bogaerts was intent on remaining with the Red Sox and was willing to sign the team-friendly deal, even after Boras advised against it. (The opt-out clause, suggested by Boras, was a hedge against the contract becoming even more team-friendly).
The Red Sox are aware of the influence Boras wields and though the meetings between Boras and team ownership took place without Boras participating, there has been contact with him in the weeks since the end of the regular season.
* The sooner the Red Sox get some clarity with both players, the better.
If the Red Sox know they have Bogaerts signed and set, they can turn their attention to other needs on the roster, which are considerable. The Red Sox need to add experienced starting pitching, a corner outfielder, a minimum of two bullpen arms and perhaps a catcher. That's a lot of work for Chaim Bloom and his staff.
By getting Bogaerts done -- if not before his opt-out, then soon after -- they'll have a better idea about their payroll and commitments going forward. If, on the other hand, Bogaerts leaves -- and it's worth noting that Boras clients typically sign later into the offseason -- the gaping hole left at short will come to dwarf their other needs.