The 2016 Major League Baseball season ended Wednesday at Progressive Field in Cleveland with one of the most memorable Game 7s in the history of the sport. It took four-plus hours, 10 innings and a rain delay, but the Cubs defeated the Indians, 8-7, to overcome a 3-1 series deficit and break their 108-year World Series drought.

One of many heroes for Chicago was left fielder Ben Zobrist, who delivered a tie-breaking double off Indians reliever Bryan Shaw in the top of the 10th. That was the 10th hit of the Fall Classic for Zobrist, who took home World Series MVP honors. After winning a title with the Royals last November, Zobrist joined the Cubs in free agency on a four-year, $56MM deal during the offseason. The Zobrist acquisition will go down as one of seemingly countless great moves by the Cubs’ front office, led by president and chief architect Theo Epstein. Having now put so-called curses in Boston and Chicago to rest, Epstein has cemented his place in Cooperstown.

While Epstein, general manager Jed Hoyer and the rest of the Cubs’ executives will savor this triumph, their work won’t stop. With the major league offseason already starting Thursday, the Cubs will spend the next several months trying to put their roster in position to repeat in 2017. Meanwhile, the majors’ other 29 franchises will attempt to make the moves necessary to overtake the Cubs. Maybe one of those teams will even sign next fall’s version of Zobrist during the upcoming winter.

With that preamble out of the way, here are some of the offseason’s key dates:

  • Nov. 3: Beginning at 9 a.m. ET, teams will have an exclusive five-day negotiation window with their impending free agents.
  • Nov. 7: By 5 p.m. ET, teams must submit qualifying offers to their upcoming free agents. The QO is worth $17.2MM, up from $15.8MM last year. This is also the deadline for clubs to exercise their 2017 options over players whose contracts include them.
  • Nov. 8-10: General managers’ meetings in Scottsdale, Ariz. While not as active as December’s Winter Meetings, the groundwork for many trades and signings will take place here, and a few moves figure to be completed.
  • Nov. 8: Free agents become eligible to sign with any team.
  • Nov. 14: Players must choose to accept or reject qualifying offers by 5 p.m. ET. Those who decline will become free agents.
  • Dec. 1: The collective bargaining agreement between the league and the players’ union expires. Click here for the latest on CBA negotiations.
  • Dec. 2: Deadline for teams to decide whether to tender contracts to their arbitration-eligible players. The free agent market should expand to some degree on this day, albeit with relatively minor names.
  • Dec. 4-8: Winter Meetings in National Harbor, Md. This period is among the most chaotic of the year for those who follow trades and free agency — often even more so than the days leading up to the non-waiver trade deadline. MLBTR will provide extensive coverage while the Winter Meetings are in effect. The meetings with conclude with the Rule 5 draft on Dec. 8.

If you’d like to prepare for the madness ahead, check out the free agent list Steve Adams and Tim Dierkes have been updating since March 2015 (please let us know via the contact form if there are any omissions). MLBTR contributor Matt Swartz’s arbitration projections are a must-read every year, as is the writing staff’s Offseason Outlook series. We’ll also check in on some soon-to-be available players with our Free Agent Profile series, and Tim will rank the 50 best free agents of this year’s class by potential earning power and predict where each will sign. Although the open market won’t be rife with appealing free agents this offseason, the next few months will still feature plenty of excitement. We’re looking forward to covering the action.

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