MLB Offseason: Key dates, deadlines and things to watch this winter

It’s been a quiet few weeks for the Red Sox, who have sat on the sidelines watching the MLB playoffs unfold, but things will quickly pick up in the days to come.

Once the World Series ends, the baseball world will shift into offseason mode, and throughout November there will be a near daily drumbeat of dates and deadlines that will be of interest. So what can fans expect? Here’s a quick primer on the offseason schedule and how things will play out this winter.

Free agent market to ramp up

The free agent and trade markets officially open the day after the World Series concludes, but free agents can’t sign with new clubs until five days afterwards, giving clubs an exclusive five-day window to re-sign their own players.

This year the Red Sox have eight pending free agents – starters Nick Pivetta and James Paxton, outfielder Tyler O’Neill, catcher Danny Jansen, and relievers Kenley Jansen, Chris Martin, Luis Garcia and Lucas Sims. Paxton has already announced his retirement and it’s not clear if any of the others will return.

Decisions on player, club and mutual options must also be made within five days of the World Series’ end. Starting pitcher Lucas Giolito has a $19 million player option he has already confirmed he’ll pick up, and the Red Sox have a $2.1 million club option for outfielder Rob Refsnyder that they are expected to exercise.

Qualifying offers must also be extended within this quiet window. The qualifying offer is a one-year offer worth the mean salary of MLB’s 125 highest-paid players, which for this season has been set at $21.05 million. Players who receive a qualifying offer will have until Nov. 19 at 4 p.m. to accept, and if they reject the offer and sign with a different team, their original team will receive draft pick compensation.

The Red Sox don’t have any slam dunk candidates for the qualifying offer, though O’Neill and Pivetta are possibilities. The club did not extend any offers last winter and most recently extended offers to Xander Bogaerts and Nathan Eovaldi after the 2022 season. Both players signed elsewhere and the draft pick acquired as compensation for Bogaerts wound up being used to pick Kristian Campbell, who exploded onto the scene this year to become a top 25 prospect.

Salary arbitration

Jarren Duran and Tanner Houck both enjoyed All-Star seasons, and Kutter Crawford established himself as a reliable big league starting pitcher. Yet the three combined to earn less than $2.5 million in 2024, per Spotrac.

It will be a while before they hit free agency, but all three are expected to enjoy significant raises this offseason.

Players who have three or more years but fewer than six years of big league service time, along with a small group of players with between two and three years, are eligible for salary arbitration if they haven’t already agreed to a long-term contract extension with their club. Duran, Houck and Crawford are Boston’s three arbitration-eligible players and should expect their salaries to more than triple.

In its annual salary arbitration projections, MLB Trade Rumors projects Duran will receive $4.9 million, Houck $4.5 million and Crawford $3.5 million. The deadline for arbitration-eligible players and their clubs to agree to a contract is typically in early January, and those who can’t reach an agreement go to salary arbitration, with hearings commencing throughout late January into February.

Clubs can also decline to tender a player on their 40-man roster under team control a contract for the upcoming season. Those players are “non-tendered” and become free agents. The deadline to tender player contracts this year is Nov. 22.

Meetings, awards and more

This year’s MLB Winter Meetings will take place Dec. 9-12 in Dallas, Texas. Beyond the potential for major trades or free agent signings, the meetings also play host to two of the offseason’s biggest events, the MLB Draft Lottery and the Rule 5 Draft.

The second annual Draft Lottery will take place Dec. 10. After finishing 81-81 and with the 13th-worst record in baseball, the Red Sox have a 1.22% chance of landing the No. 1 overall pick. The most likely outcome is the Red Sox pick at No. 13 overall, though they could also get bumped further down the board if any clubs behind them jump into the lottery.

The Rule 5 Draft, which will take place Dec. 11, allows clubs to identify and offer a big league opportunity to a minor leaguer who hasn’t been given a shot elsewhere. The idea is to keep teams from hoarding MLB-ready talent in the minors, and the Red Sox have recently been among the draft’s biggest beneficiaries — Garrett Whitlock and Justin Slaten were both recent Rule 5 selections.

Any minor leaguer who isn’t on a 40-man roster and who is either four or five years out from signing their first professional contract is eligible to be selected, so in the lead-up to the Winter Meetings clubs must decide which of their Rule 5-eligible prospects they want to protect. This year the deadline to finalize the 40-man roster is Nov. 19. The Red Sox’s most likely candidate for protection is right-hander Hunter Dobbins, though Michael Fulmer, a former AL Rookie of the Year who spent all of last year in the minors rehabbing from elbow surgery, could be a possibility as well.

The annual GM Meetings will take place Nov. 5-7 in San Antonio, Texas, and the Owners Meetings will be Nov. 19-21 in New York City.

MLB’s major awards will also be announced throughout November. Gold Glove winners will be unveiled on Nov. 3, Silver Slugger winners on Nov. 12 and the Hank Aaron Awards, Comeback Players of the Year, Mariano Rivera and Trevor Hoffman Relievers of the Year, Edgar Martinez Outstanding Designated Hitter of the Year, and selections for the All-MLB First and Second Teams will all be announced on Nov. 14 as part of the “All-MLB Team Show” live in Las Vegas.

The BBWAA’s awards will be presented over the following week. Rookie of the Year winners will be announced Nov. 18, Managers of the Year on Nov. 19, the Cy Young Awards on Nov. 20 and MVP winners on Nov. 21. The MLB Players Alumni Association’s Heart and Hustle Award will be announced on Nov. 22.