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Key dates for the White Sox as the offseason begins

Chris Sale literally ended the World Series last year with the clinching strikeout.

Adam Eaton figuratively ended the World Series this year with a bases-loaded two-run single that turned a two-run lead into a four-run lead with one inning to go.

Rick Hahn can indeed push a team over the top, provided you don't care which team it is.

Free agency officially begins today, and the aftermath of Game 7 underscored just how abrupt the process is, because Gerrit Cole answered postgame questions as a man without a country.

HOUSTON — His team just having suffered a stunning World Series Game 7 loss to end its season, Gerrit Cole held an awkward exchange with an Astros media relations official about speaking to the media late Wednesday.

“I’m not employed by the team,” declared the right-hander, who then relented, “I guess as a representative of myself …” and placed himself in front of a group of reporters.

Cole will have his pick of potential employers. The hope for everybody is that he'll pick sooner rather than later. Rob Manfred said he wants to see more activity during the winter meetings, but it remains to be seen whether owners will want to pay for it.

At any rate, White Sox fans have been ready for the offseason for quite some time. It starts today, and here's a rough timeline of key dates between now and San Diego.

Next five days: Players declare for free agency, or get sent there when their options are bought out, in the case of Welington Castillo. Players declare for free agency, White Sox can negotiate with Jose Abreu or issue him the qualifying offer. They'll presumably lose the phone numbers of anybody else they can retain save Hector Santiago, who is still on their Christmas card list.

The White Sox will also wait to see if J.D. Martinez opts out of the three years and $62.5 remaining on his contract. The rest of baseball will watch to see if the Nationals can retain Stephen Strasburg and/or Anthony Rendon. Strasburg was one of the few Scott Boras clients to sign an extension, and MLB.com's Mark Feinsand said "the feeling in the industry" says he'll use the opt-out as leverage to add a couple more years to his stay in Washington. Rendon seems more likely to test the market as the top position player available, but the Nationals have surprised before.

After that?

Nov. 3: We'll find out if Yolmer Sánchez and Lucas Giolito win Gold Gloves.

Nov. 4: We'll find out if Giolito or Eloy Jiménez are finalists for Cy Young and Rookie of the Year. Respectively, of course.

Nov. 7: Silver Slugger Awards announced, giving Abreu, Tim Anderson and Yoan Moncada a shot to add some hardware, because Joe Crede will tell you it doesn't always make sense.

Nov. 8: We'll see if Jiménez can steal any first-place votes away from Yordan Alvarez for AL Rookie of the Year.

Nov. 11-14: General managers meetings in Scottsdale, Ariz.

Nov. 13: We'll see how many Cy Young votes Giolito earned.

Nov. 14: Deadline for players to accept or reject the $17.8 million qualifying offer. Also, the MVP ballots are released, and we'll see if Abreu, Yoan Moncada or Tim Anderson receive down-ballot support.

Nov. 18: We'll find out if Lucas Giolito wins the Comeback Player of the Year Award, and whether people care about the award enough to debate if he'd established himself firmly enough to "come back" from anything.

Nov. 19-21: Owners meetings in Arlington, Texas.

Nov. 20: Deadline to add prospects to the 40-man roster or risk losing them to the Rule 5 draft. I'm guessing that Dane Dunning, Jimmy Lambert and Zack Burdi will be added, while Yermin Mercedes, Bernardo Flores and Blake Rutherford have the most compelling bubble cases.

Dec. 2: The non-tender deadline, where the Sox have to determine how many of the eight arbitration-eligible players they'd want to retain. I reviewed the potential options here.

Dec. 9-12: The Winter Meetings in San Diego, which Josh will attend.

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