MLB Trade Rumors posted an off-season calendar last week, detailing the order of operations for the winter. It's useful as a rough outline, but isn't team-specific. For that, you come to a team-specific site: here's how that calendar looks with a little more Red Sox flavor in there.
- Post-World Series: Eligible players become free agents. For Boston, that means David Ortiz, Daisuke Matsuzaka, James Loney, Cody Ross, Aaron Cook, Vicente Padilla, and Scott Podsednik.
- Three days after the World Series: Decisions on options are due. The World Series ended on Sunday, October 28. That means decisions on options are due by the end of October 31. However, Boston has no options to make a decision on at all, so, at least this year, this particular date doesn't apply.
- Five days after the World Series: Otherwise known as November 2, this is the day when qualifying offers are due to free agents. The Red Sox could extend a qualifying offer to any of the above seven free agents, but they won't: the only one who would merit the qualifying offer would be David Ortiz, and Boston is reportedly near completion on a two-year deal with him to retain the DH's services. The qualifying offer is part of the new collective bargaining agreement, and replaces arbitration as the way to receive draft compensation for the loss of a free agent. A flat offer of $13.3 million -- the average of the top 125 salaries in baseball -- is sent to the player, who can either accept the one-year deal and stay, or head elsewhere. Should the player in question sign with a new team, the original club receives a first-round draft pick, while the team that signed the player loses their first-available pick. The top 10 picks in the draft are protected, but otherwise, they are all game to be lost in this system.
- Six days after the World Series: On November 3, qualifying offer in hand or no, free agents can begin to sign contracts with clubs other than their last. This is the date Boston is hoping to have David Ortiz locked up before, and presumably, Cody Ross as well. The rest of the free agents are unlikely to return, and if they do, it won't be until later in the off-season, at a time when Boston likely has all the leverage.
- 12 days after the World Series: Players who received qualifying offers must accept or reject them. Rejection would not mean that compensation is voided -- it's no different than a player who, offered arbitration, declines to accept it and heads out into free agency. This will occur during the general manager meetings, which start on November 7 and end November 9.
- November 20: This is the date that the 40-man roster has to be set, in order to protect players against the Rule 5 draft. Boston's new Rule 5 eligible players include Josh Fields, Alex Wilson, Chris Balcom-Miller, Dan Butler, Miguel Celestino, Jose De La Torre, William Cuevas, Alex Hassan, Jeremy Hazelbaker, Ryan Pressly, Christian Vazquez, Allen Webster, and more. Webster will absolutely be added to the 40-man, while pitchers like Alex Wilson and Josh Fields will either be added or traded prior to this date, in order to avoid losing them for nothing. Christian Vazquez might be the other protected party, in order to keep someone who has already lost 2013 before it begun -- say, the Astros -- from stashing a potentially useful catcher on their roster.
- November 30: Arbitration isn't gone, it just lost some of its privilege under the new CBA. Contracts need to be tendered to arb-eligible players by this date. For the Red Sox, that's an extensive list: Jacoby Ellsbury, Jarrod Saltalamacchia, Craig Breslow, Ryan Sweeney, Andrew Bailey, Daniel Bard, Alfredo Aceves, Andrew Miller, Franklin Morales, Rich Hill, and Junichi Tazawa.
- December 3-6: The winter meetings will take place -- this is likely to be the hotbed of off-season activity, as it normally is. Not everything happens here, but things happen with the most frequency. Boston has players to deal, but because of their 40-man situation, they might be moved before the meetings. It's a bit up in the air at the moment how much of Boston's off-season will occur during this stretch.
- December 6: The Rule 5 draft will occur, and Boston is more likely to lose a player than they are to acquire one.
- In the last two months of the off-season, arbitration figures will be swapped between teams and players, and then in February, necessary hearings will occur. Boston hasn't had a player head to arbitration in years, with Theo Epstein's entire regime going without such an incident, and Ben Cherington keeping with that trend in his first year on the job. The only player there might be some contention with is Jacoby Ellsbury, who the Sox might not want to give a significant raise to considering his time missed in 2012, but even that's a stretch -- it will likely be solved well before hearing time.