The Red Sox, along with the rest of baseball, are basically in a holding pattern until the World Series, which is scheduled to run from Oct. 22-30.
Once the final out is recorded, however, the offseason begins in earnest. Here are some dates of note, particularly in relation to the Red Sox.
One day after World Series -- Free agency filing
In the case of the Red Sox, this primarily means Rick Porcello, Mitch Moreland, Steve Pearce, and Brock Holt. With the Red Sox looking to cut costs, none is expected to return. This begins the five-day quiet period where teams can only negotiate with their own free agents.
Five days after World Series -- Opt-out deadline
Teams must decide whether to extend one-year qualifying offers of roughly $18 million to their pending free agents, who then have 15 days to accept. This is also the deadline for players to exercise opt-outs, which for the Red Sox means J.D. Martinez. The Red Sox can still make Martinez a qualifying offer, which will entitle them to draft pick compensation if he signs elsewhere. Qualifying Martinez is an easy decision, since he will decline it and then draw interest as the premier slugger on the market if he opts out. This could be the day his Red Sox career officially ends, especially if the team intends to cut nearly $40 million in payroll to drop below the $208 million luxury tax threshold.
Nov. 3 -- Gold Glove winners
The only Red Sox with shots at nominations are center fielder Jackie Bradley and right fielder Mookie Betts, both defending winners. Betts is shooting for his fourth straight award, while Bradley is gunning for his second. While Betts remains an elite defender statistically, the advanced metrics suggested a down year for Bradley, for whatever that's worth.
Nov. 4 -- Awards finalists
The Red Sox are unlikely to factor into any of these announcements, which reveal the three finalists in each of the major awards. While in other years shortstop Xander Bogaerts, third baseman Rafael Devers, and even Betts could make cases for MVP consideration, they shouldn't sniff the top three, not with Anaheim's Mike Trout, Houston's Alex Bregman, and Oakland's Marcus Semien dominating the WAR leaderboard. Left-hander and 19-game winner Eduardo Rodriguez will earn some Cy Young votes, but not enough to finish in the top three of a group that includes Houston's Justin Verlander and Gerrit Cole, as well as Texas left-hander Mike Minor.
Nov. 7 -- Silver Slugger Awards
The Red Sox could be well-represented here, between Bogaerts, Betts, and Martinez. As great a year as Devers had, Bregman (.296-41-112) was better. Martinez will be competing primarily against AL home run leader Jorge Soler of the Royals and ageless Twins slugger Nelson Cruz.
Nov. 11-14 -- GM meetings
The meetings will be held in Scottsdale, Ariz., and we have no idea who'll be calling the shots for Boston. For now, it's the four-headed monster of Eddie Romero, Brian O'Halloran, Zack Scott, and Raquel Ferreira. It could also be a new head of baseball operations, whether that's Andrew Friedman, Chaim Bloom, Billy Beane, Derek Falvey, or maybe even Theo Epstein. With ownership pledging to take its time finding a replacement for Dave Dombrowski, and virtually every executive in the game on site, don't be surprised if these meetings end up serving as a recruiting trip.
The major award winners will also be announced over these four days, but as noted earlier, the Red Sox won't factor in Rookie of the Year, Manager of the Year, Cy Young, or MVP.
Nov. 18 -- Comeback Players of the Year
This award is only worth noting for the candidates the Red Sox could field next year -- namely, Chris Sale and Nathan Eovaldi, and maybe David Price.
Nov. 19 -- Designated Hitter of the Year
As mentioned above, this one should come down to Martinez, Soler (who played 56 games in the outfield), and Cruz.
Nov. 19-21 -- Owners Meetings
Will the Red Sox have a GM yet? With the winter meetings only three weeks away, let's hope so.
Dec. 2 -- Non-tender deadline
The Red Sox will have some decisions to make among their arbitration-eligible players. Catcher Sandy Leon and knuckleballer Steven Wright feel like candidates to be set free. Everyone else should be tendered: Betts, Bradley, E-Rod, Matt Barnes, Heath Hembree, Brandon Workman, Andrew Benintendi, and Marco Hernandez. There's a remote shot the Red Sox could cut Bradley free rather than offer him arbitration and a salary that will finish north of $10 million, but they're far more likely to tender him and then trade him this winter.
Dec. 9-12 -- Winter Meetings
The industry's annual gathering, held this year in San Diego, used to be a time for wheeling and dealing. But with teams and agents content to push off decisions into February and even March, it's not the wham-bam showcase it used to be. The Red Sox should be among the most active participants, however, given their many, many needs -- gauging a Betts trade market, finding multiple cheap starters, potentially moving Bradley, searching for a utilityman, backup outfielder, DH, and maybe even a first and second baseman. They should hopefully have selected a GM by this point.
Dec. 12 -- Rule 5 draft
The Red Sox used to be active in the Rule 5 draft, which exposes minor league players with either four or five years of service time (depending on their age when they signed) who aren't on a 40-man roster. They've landed solid big leaguers like left-hander Javier Lopez and jack-of-all-trades Marwin Gonzalez (whom they immediately traded to the Astros in 2011). They've also lost some effective players, like relievers Josh Fields and Ryan Pressly, both in 2012. Under Dave Dombrowski, they basically ignored the Rule 5, taking only veteran infielder Josh Rutledge from the Rockies in 2016. Given their need for cheap talent, don't be surprised if they're more active this year. Players selected must remain on the 25-man roster all season or be offered back to their original clubs for $25,000.
Jan. 10 -- Arbitration figures exchanged
If Betts is still here, then he'll be looking at anywhere from $27-$30 million. Per the invaluable projections at MLB Trade Rumors, here's what the rest of the arb-eligible Red Sox should expect:
Bradley ($11 million), Rodriguez ($9.5 million), Benintendi ($4.9 million), Brandon Workman ($3.4 million), Matt Barnes ($3 million), Chris Owings ($3 million), Leon ($2.8 million), Hembree ($1.6 million), Wright ($1.5 million), Gorkys Hernandez ($1 million), Marco Hernandez ($700,000).
Arbitration hearings will then be held from Feb. 3-21 in Phoenix.
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