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White Sox offseason calendar

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All the dates you need to know to stay South Side smart this winter

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MLB: Cleveland Indians at Chicago White Sox Dennis Wierzbicki-USA TODAY Sports

Welcome to The Most Important Offseason Ever™!

Given its importance, in theory, and the complicated calendar, it makes sense to have a thumbnail sketch of what’s happening between Halloween and Opening Day.

As we did last year, here’s a compendium of offseason dates, and we’ll keep it pinned somewhere, probably right below the top stories, all offseason for you to refer to. If something is missed (or wrong), lemme know and we’ll correct it.


October 31: Players file for free agency

Prospective free agents were dropped from 40-man rosters the day after World Series, which kicked off a five-day exclusive window for teams and their own free agents to negotiate, and on the White Sox, that window applies to José Abreu, Ross Detwiler, Jon Jay, Iván Nova and Héctor Santiago. It would not be a shock that “lifetime White Sox” Abreu re-signs in early November, during this window.

November 2: Offseason plans

Like Christmas shopping season, offseason plan season seems to get earlier every year. Many of you have already submitted plans for this offseason, because why enjoy the World Series when there’s only ... uh ... 15 weeks or so ahead of us without baseball. Anyway, SSS will host the longest-running fake GM hoedown once again, beginning here.

November 3: Gold Glove Awards

The first of the major awards to be handed out this winter are Rawlings’ Gold Gloves. The White Sox have two players among the three finalists per position in each league: Yolmer Sánchez and Lucas Giolito.

November 3: SBNation GM simulation begins

From Sunday through Tuesday, SBN holds its annual offseason GM meetings, and for the second year Brett will represent the White Sox (along with several assistant GMs). The roster he put together last year I sense was far better than the overall slop Rick Hahn came up with for 2019, but I think there will be a summary on SSS to kickoff Sunday, so we can all see if that’s true.

November 4: Award finalists announced

Like the Gold Gloves announcing finalists a week before awards are handed out, the BBWAA does the same. Expect Eloy Jiménez to be a AL Rookie of the Year finalist and Giolito possibly cracking a Cy Young Top 3, but otherwise, the White Sox will be shut out (Manager of the Year, MVP). You can watch the announcements on MLB Network at 5 p.m. Central.

November 4: Option deadline/qualifying offers extended

Five days after the World Series ends, things start to get moving. Teams and players with contract options must decide whether to stay or go. Now, with the odd swap of Welington Castillo to Texas, the White Sox have no pending options to contend with. But that doesn’t mean the team won’t be looking around the league with great interest, particularly with Boston’s J.D. Martinez possibly opting out of the three years and $62.5 remaining on his contract and Washington’s Stephen Strasburg doing same. Both are likely White Sox targets if and when they opt out.

November 6: Wilson Defensive Player of the Year Awards announced

I don’t know what this is. I’m guessing it’s some sort of metricky take on the Gold Gloves, only presented by glove manufacturers Wilson, not Rawlings. You can watch the awards on MLB Network at 5 p.m. Central.

November 7: Silver Sluggers announced

Possible winners for the White Sox include Tim Anderson, Yoán Moncada and Abreu. Moncada could very well end up as a perennial Silver Slugger and Gold Glove finalist. You can watch the awards on MLB Network at 5 p.m. Central.

Early November: Veteran’s Hall of Fame Committee ballot announced

The 10 candidates for the Modern Baseball Era Committee’s ballot, to be voted on at the Winter Meetings, will be announced. Though we have no idea of the actual ballot, Ted Simmons and Marvin Miller have garnered strong past support, and Steve Garvey, Tommy John, Don Mattingly, Dale Murphy, Luis Tiant and Dave Parker also stand a chance, depending on the makeup of the committee.

November 11-14: GM Meetings

The precursor to December’s white-hot Winter Meetings are the GM Meetings a month earlier. The three days in Scottsdale, Ariz. will be spent feeling out other teams on trade talks and sometimes also front office/managerial moves, but don’t expect a lot of player movement. An minor trade or two is usually the most we can hope for.

November 11: Rookie of the Year Awards announced

Yordan Álvarez of the Astros is a given, it seems, in the AL. But on this day, we’ll find out how close Jiménez came to an upset. You can watch the awards on MLB Network at 5 p.m. Central.

November 12: Manager of the Year Awards announced

Minnesota’s Rocco Baldelli seems the popular pick in the American League. Somehow, I don’t think Ricky got a vote. You can watch the awards on MLB Network at 5 p.m. Central.

November 13: Cy Young Awards announced

Houston is assured of a winner in the AL, the only question being whether Gerrit Cole or Justin Verlander gets the hardware; Cole seems to have the edge. Giolito will garner votes, so let’s see how close to the top he finishes. You can watch the awards on MLB Network at 5 p.m. Central.

November 14: MVP Awards announced

It’s another two-man race in the AL, but this time not between teammates. Alex Bregman and Mike Trout are the frontrunners, and I’d say both the smart and sentimental choice is Trout. Way downballot, Giolito or Abreu could get a vote or two, perhaps even Moncada. Or Anderson, for big STICK TALK fans. You can watch the awards on MLB Network at 5 p.m. Central.

November 14: Deadline to accept/decline qualifying offers

There’s no impact here for the White Sox, as Abreu is more likely to sign an extension than be extended a qualifying offer, unless the White Sox look at him as having only one year left (sounds about right, given their MLB scouting prowess). Offhand I’m unsure what players the White Sox might be targeting who are vulnerable to the $17.8 million QO, but if I spaced on someone, lemme know in the comments.

November 19-21: Owners Meetings

The meetings are in Arlington, Texas this year. Will there be discussion about the baseball and a vote on whether to go “live” or “dead” in 2020 (preferably, not one ball in the regular season and a different one in the post)? Will something about the CBA or minor league baseball negotiations leak? Probably not. You’ll be excused for snoozing through these.

November 20: Rule 5 protection deadline

Teams submit their 40-man rosters to MLB by November 20, so by then we’ll know which White Sox prospects have made the jump to can’t-lose. Back in August old friend WSM put together an exhaustive 40-man primer over at South Side Hit Pen, which included these names as likely possibly 40-man additions: Dane Dunning, Blake Rutherford, Zack Burdi, Bernardo Flores, Danny Mendick, Jacob Lindgren and Yermín Mercedes. It’s a great read, and also includes those players vulnerable to being designated off of the 40-man.

December 1: Hall of Fame veteran’s committee voting begins

For the first time, we’re going to vote on the overlooked superstars from the past, in our own veteran’s committee vote (Dick Allen, Bob Grich, Minnie Miñoso, Gil Hodges, etc.) We’ll try to round up the Top 20 or 30 stars so far ignored the by Cooperstown, and put ’em to a vote. Voting will be held over at South Side Hit Pen. This one’s gonna be fun.

December 2: Non-Tender deadline

The White Sox will have to decide whether or not to offer arbitration to five players by this day: Alex Colomé, James McCann, Leury García, Yolmer Sánchez and Carlos Rodón. Given his usefulness measured against anticipated salary, Sánchez seems the only player in jeopardy of being non-tendered.

December 9-12: Winter Meetings

The highlight of the winter are the Winter Meetings, although last year’s was a flop and most of the juicy signings will come in early 2020, if trends hold. San Diego will still be hopping with all manner of baseball talk, and trades and other controversies make this the most thawed week of the offseason.

December 12: Rule 5 draft

At the end of the Winter Meetings is the Rule 5 draft. The White Sox haven’t been very active here lately, but all it takes is one targeted name left unguarded and it all can change.

December 15: Hall of Fame voting begins

We’ll vote in another Hall of Fame class this year, and this will be the first year voting will be held over at South Side Hit Pen. Derek Jeter is the only obvious first-timer in this year’s class, so hopefully some of the overlooked stars of the past can squeak in as well.

December 16: SSHP Top 100 Prospects begin

We’ll be duplicating last year’s Top 100 Prospects countdown, only this year it will be at South Side Hit Pen.

January 9: White Sox Hall of Fame voting begins

The third annual White Sox Hall of Fame voting begins, lasting two weeks, with the 2020 class announced ahead of SoxFest. Again, this year the voting will be at South Side Hit Pen.

January 10: Exchange of arbitration figures

This is when players send their desired salary to teams, and teams let players know what they want to pay. Traditionally, the White Sox avoid arbitration with their players, preferring to work out deals well in advance. Contracts can still be forged after this date, but it’s often more complicated than just splitting the difference.

January 21: Hall of Fame results announced

Derek Jeter is the only shoo-in among the first-timers on this year’s ballot, so 2020 will be a good year to enshrine some long-overdue players.

January 24-25: SoxFest

The White Sox hold their first Friday-Saturday SoxFest, and at a new location, McCormick Place. It’s the 28th year of SoxFest, and if you’ve never gone, give it a whirl, it’s great fun. Tickets are still available for everything but the all-new Breakfast With the Sox Experience.

February 3: Arbitration hearings start

Any players eligible for arbitration who haven’t yet been locked up by their teams will have hears in February. Independent arbiters will decide between the figures exchanged three weeks earlier, and the arbitration process is win or loss — no splitting down the middle.

Mid-February: pitchers and catchers report

No exact reporting date has been announced yet, but pitchers and catchers will report somewhere around February 10-12.

February 22: Spring Training opener

The White Sox host the Angels at Camelback Ranch on the second Saturday after pitchers and catchers report, kicking off another Cactus League season.

March 26: Opening Day

Lord in heaven, the White Sox open at home ... in March ... hosting the Kansas City Royals.