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MLB Offseason Calendar

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All of the dates you need to know this winter.

Chaim Bloom Press Conference Photo by Billie Weiss/Boston Red Sox/Getty Images

Well, as this is being published we have just one more day left for MLB baseball to be on our lives. As soon as this Game Seven ends between the Nationals and Astros on Wednesday, it’s time for the offseason. There is a lot that goes on over the winter for baseball, and it can be confusing to keep all of the dates in mind. I know every year I find myself Googling one event or another to see how far away we are. So, this year I’m just putting them all in one place and I’ll pin this on the front page so you always know where to go when looking for certain offseason markers.

October 31: Players may file for free agency

Players set to hit free agency will officially come off 40-man rosters the day after the World Series ends, though they cannot yet sign with other teams. This begins a five-day quiet period in which players and their previous teams may negotiate. For the Red Sox, the following players are among those joining the free agent pool this winter: Rick Porcello, Brock Holt, Mitch Moreland, Steve Pearce and Jhoulys Chacín. The expectation from me at this point is that none of them will be back in 2020, though there is at least some case for each of them.

November 3: Gold Glove Awards Announced

The first of the major awards to be handed out this winter, as always, will be the Gold Gloves. The Red Sox were not great in terms of run prevention this year, but they had some standout defenders who earned Gold Glove Finalist nods. Mookie Betts, Jackie Bradley Jr., Andrew Benintendi and Christian Vázquez are all up for the award.

November 4: Option Deadline/Qualifying Offers Extended

Five days after the World Series ends, the first major decision of the Red Sox offseason will have been made. Teams and players with options in their contract must make their decisions on whether or not to execute said options by this point. For the Red Sox, this means J.D. Martinez. The slugger has an opt-out in his contract and at this point it is not clear at all in what direction he’s leaning. We’ll know by this date what he decides. Also on this date teams can extend qualifying offers to their departing free agents. Martinez, if he does opt out, is the only player for the Red Sox for whom this is realistic. This year the qualifying offer is set at $17.8 million, actually dropping by $100,000 from last winter.

November 4: BBWAA Award Finalists Announced

The BBWAA awards were all voted on prior to the start of the postseason, but we obviously don’t learn the results until after the games are finished. I still don’t understand why we need to have finalists since it’s really just saying who the top three in voting are, but presumably it drums up interest. I’ll take their word for it. The awards here are Rookie of the Year, Manager of the Year, Cy Young and MVP.

November 7: Silver Sluggers Announced

The hitting version of the Gold Gloves, as I like to call them, will be announced on November 7. Possible winners for the Red Sox include Christian Vázquez, Xander Bogaerts, Rafael Devers, Mookie Betts and J.D. Martinez. Also, just a reminder that J.D. Martinez won two Silver Sluggers in 2018. We don’t talk about that enough.

November 11-November 14: GM Meetings

The first real Hot Stove-y event of the offseason starts on November 11 when the GM Meetings take place in Scottsdale, Arizona. This isn’t really a place where a ton of major moves get made, though there will be some here and there. Instead, we’ll start to hear a lot of rumors about who could be available in trades as well as start to hear some free agency connections.

November 11: Rookie of the Year Announced

The first of the BBWAA awards is announced here. The Red Sox don’t have any real candidates here, although Michael Chavis did look like one for a month or two early in the year. The clear favorite in the American League is Yordan Álvarez of the Astros while Pete Alonso of the Mets is likely to win in the National League.

November 12: Manager of the Year

The award for best manager comes second in this awards week, and again the Red Sox aren’t getting any love here. I would guess Rocco Baldelli and Mike Shildt are the favorites, though I think I’d lean towards Aaron Boone in the American League.

November 13: Cy Young

The Cy Young awards are going to be fascinating this year. In the American League it’s a two-man race from the same team with Gerrit Cole and Justin Verlander having equal cases from the Astros rotation. I honestly think splitting the award would be the right call, but if I had to choose I’d probably go Cole. In the National League it probably comes down to Jacob deGrom and Max Scherzer, and I’d lean towards the former.

November 14: MVP

The Red Sox will get some love in the MVP voting, though it won’t be near the top of the ballot. The AL ballot is going to come down to Alex Bregman and Mike Trout, and I suspect the vote will be very close. I would go with Trout, but I don’t think it’d be a total travesty if it went to Bregman, something I’ve changed my mind on recently. Betts, Bogaerts and Devers could all get some down-ballot votes here. In the National League, Cody Bellinger is the the favorite, though Christian Yelich could still be a factor despite his late-season injury.

November 14: Deadline to Accept/Decline the Qualifying Offer

This one doesn’t have a tremendous impact on the Red Sox unless Martinez does opt out and they extend him the qualifying offer. Presumably, if he does opt out he would decline this offer, because it would make no sense to opt out then take a one-year deal for less money than he had on the table. If Martinez does opt out and decline the qualifying offer, the Red Sox would gain a draft pick following the fourth round in next summer’s draft. As for the other free agents, it seems very unlikely Boston will target anyone good enough to earn a qualifying offer.

November 19-November 21: Owners Meetings

Generally, these meetings aren’t that important for our purposes. Some new rules may be discussed, but mostly it’s business stuff that I’d prefer not to worry about. This year, however, the CBA will be hanging over everything and that is sure to come up over these few days in Arlington, Texas.

November 20: Rule 5 Protection Deadline

Teams must submit their 40-man rosters by November 20, which essentially means they need to protect their prospects from the Rule 5 Draft. Anyone who meets the service time criteria and is not on the 40-man roster can be selected in the Rule 5 draft a few weeks after this. This year Boston could protect a number of players like Bobby Dalbec, C.J. Chatham and Yoan Aybar, among others. We’ll have more on this as the deadline gets closer.

Note: A previous version of this story included Tanner Houck, who is not Rule 5 eligible until next winter.

December 2: Non-Tender Deadline

By this day, teams must decide to which of their arbitration eligible players they will tender contracts. For the Red Sox, assuming they have not been traded by this point, the following players are slam dunks to be tendered deals: Betts, Benintendi, Bradley Jr., Eduardo Rodriguez, Brandon Workman, Matt Barnes and Marco Hernandez. Sandy León and Heath Hembree are candidates to be non-tendered and made free agents.

December 9-December 12: Winter Meetings

The Winter Meetings are, of course, the main event of every baseball offseason. They are becoming less and less intriguing every year, though, largely because they just aren’t necessary in the same way. They still serve as something of a convention for baseball enthusiasts, but front offices have so many ways of instant communication today that these face-to-face meetings just aren’t as important. Still, with all of the rumors sure to be swirling around the Red Sox we’ll be stressing throughout this week. This year’s Winter Meetings are in San Diego.

December 12: Rule 5 Draft

As always, the final event of the Winter Meetings will be the Rule 5 Draft. We’ll again have more on this as the event gets closer, but the Red Sox are generally pretty quiet here.

January 10: Exchanging of Arbitration Figures

The first big date after the New Year is when teams and players must exchange arbitration figures. For the Red Sox, they are generally pretty good at agreeing to terms before this comes into play, though they haven’t been as efficient in recent years as they were in the previous decade. Teams and players can still negotiate deals after figures are exchanged, but some teams use this as a hard deadline for negotiations. For what it’s worth, the Rays have been a “file-and-trial” team in the past.

January 17-January 19: Winter Weekend

Hat tip to @SteveMorge on the ol’ Twitter Machine for letting me know I forgot this one. The annual party — for lack of a better word — leading up to spring training is going to be in the middle of January this year. It will also be in a new location, moving from it’s old home at Foxwoods to its new home at MGM in Springfield. I have never been, but everyone I know who has gone has thoroughly enjoyed themselves.

January 21: BBWAA Hall of Fame Results Announced

I hate this time of year, but I know people like it so I’ll include it. The BBWAA’s Hall of Fame results are announced on January 21. Everyone will hate it, just like every year. Derek Jeter and Bobby Abreu are among the notable first timers on this year’s ballot. Larry Walker is in danger of falling off.

February 3: Arbitration Hearings Begin

If arbitration-eligible players and teams have still not agreed to deals for the 2020 season by this day, hearings will begin. Hopefully, the Red Sox will not have any of these. If they do, independent arbiters will decide between the two figures that were exchanged on January 10. There is no compromise once it gets to hearing.

February 10-February 12: Pitchers and Catchers Report

The Red Sox have not yet announced when they are reporting to Fort Myers, but this is the range in which it will fall.

February 21: Northeastern Game

We don’t know when the first official report date will be for the Red Sox, but we know this will be when they first start their game action. As always, they’ll start with a game against Northeastern.

March 26: My Birthday (And also Opening Day)

It being my birthday is the real important part here, but also it’s pretty cool that the regular season begins. Boston’s season will kick off in Toronto.