Red Sox

Red Sox MLB offseason calendar: Important dates to remember for arbitration, free agency, opt outs

Red Sox MLB offseason calendar: Important dates to remember for arbitration, free agency, opt outs

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.

Click here to download the new MyTeams App by NBC Sports! Receive comprehensive coverage of your teams and stream the Celtics easily on your device.

Ex-Red Sox not named Mookie Betts off to lackluster starts across MLB

Ex-Red Sox not named Mookie Betts off to lackluster starts across MLB

Chaim Bloom had no choice but to deal Mookie Betts. The rest of the players he walked away from this winter were of his own volition, however, and on that front, it looks like he made some good calls.

Bloom elected to keep first baseman Mitch Moreland, who has already blasted three homers while slugging .762.

Get the latest news and analysis on all of your teams from NBC Sports Boston by downloading the My Teams App

Here's a quick check-in with the four others who played a regular role in recent years but are now elsewhere. (And Betts, for the record, is hitting .289 with an .880 OPS, though he has missed two games with a finger injury).

David Price

Bloom traded Price to the Dodgers alongside Betts in a salary dump. We won't know if he made the right call until Price returns to action next season, because he became the highest-profile player to opt out of the 2020 season after the pandemic hit.

That decision likely saved the Red Sox the roughly $6 million they owed of his prorated salary this year. Had he remained in Boston, there's no reason to think he still wouldn't have opted out, so the Red Sox were lucky to get something for him first.

Rick Porcello

Hoo boy. The Mets gave Porcello one year and $10 million, and some believed the Red Sox should've ponied up to keep him, figuring his reliability could help patch the holes in a thin rotation. Bloom thought otherwise, and two starts into Porcello's Mets career, it's hard to argue.

Porcello allowed seven runs in two innings in his debut, and wasn't much better in his second start on Friday in Atlanta, allowing four runs in four innings. He's sitting on a 13.50 ERA that would fit perfectly in Boston, unfortunately.

Brock Holt

The fan favorite utility guy languished for most of the winter before agreeing to a one-year, $3.25 million contract with the Brewers. Bloom decided to allocate those resources instead to Jose Peraza, who is now the team's starting second baseman.

Holt has barely gotten off the bench in Milwaukee, going 0 for 4 in four appearances. At age 32, his best days are likely behind him. The 26-year-old Peraza has slumped badly since a four-hit debut, but he's a far superior defender at second and short.

Sandy Leon

Outside of a couple of good weeks in 2016, Leon is what he is offensively. Currently, that's a .105 hitter with the Indians.

He effectively traded roles in December with former Cleveland backup Kevin Plawecki, who's off to a 4-for-10 start that helped make two-time All-Star Jonathan Lucroy expendable.

Andrew Benintendi is struggling for Red Sox, and J.D. Martinez can't help him

Andrew Benintendi is struggling for Red Sox, and J.D. Martinez can't help him

Not even J.D. Martinez can save Andrew Benintendi at the moment.

Martinez, the veteran Red Sox DH, is known as the clubhouse swing doctor. He loves breaking down mechanics and offering tips, and preaching the gospel of launch angle helped Mookie Betts become an MVP and Xander Bogaerts a force.

Get the latest news and analysis on all of your teams from NBC Sports Boston by downloading the My Teams App

Changes to both the gameday routine as well as the availability of in-game video have curtailed Martinez's influence, however, which means slumping hitters like Benintendi have one fewer resource when the going gets tough.

"I mean, honestly, years in the past, I probably already would've been able to get in the video room, break his swing down, look at it, do some comparisons," Martinez said after Benintendi struck out with the bases loaded to end Tuesday's 5-1 defeat in Tampa. "It's kind of what I do for most of the guys on the team. Anytime they're going through some stuff, I kind of dedicate some time after the game, before the game, or something, during the game, if I just hit or something like that, I can kind of throw them a bone. As you guys know, we don't have access to any of that stuff anymore. It's kind of everyone on their own. Survivor."

There's no question that Benintendi is mired in a hellacious slump. Tuesday's 0 for 5 dropped him to .069 (2 for 29). He has struck out 12 times and rarely puts the ball in play. After fouling off a pair of good Nick Anderson fastballs in the ninth, Benintendi took a curveball for strike three, starting his walk back to the dugout before he had even officially been rung up.

A year ago, Martinez might've offered real-time advice between innings, but players no longer have access to in-game video, a change necessitated by the Astros and Red Sox stealing signs. He also could've helped well before a game, but players may no longer arrive more than five hours early, and teammates must socially distance amidst the pandemic.

"Guys are struggling and trying to work," Martinez said. "It's tough when you don't know what to work on or what to do, so everyone is feeling for stuff and it's a tough situation. We're only allowed to be here five hours before game time. That doesn't leave a lot of time for guys to go in the cage and grind it out and figure it out with the hitting coach. It's a tough hand. We've got to find a way to make it work, though. I told my guys, anytime they have anything, they know they can come up to me and ask me questions. It's just different. I don't have that time to go in and break down guys' swings and look at guys' stuff and really dive into it."

One of the players struggling most acutely is Benintendi, whose days not only in the leadoff spot, but in the lineup, period, will be in jeopardy if he doesn't start producing.

"Hard to say if he's trying to do too much," manager Ron Roenicke said. "I think he's just trying to find his -- I don't want to say his swing, because his swing is actually pretty good. I think he's trying to find his recognition of where that zone is when he does a lot of damage. Then also making sure he lays off the pitches. Usually when he's not going good, he's chasing. He's chasing down, chasing up. If he can narrow those pitches and get them back into the zone where we know he can hit, I think that's more of it than where he is in the lineup."