The New York Yankees managed to delay the offseason for a day, but Wednesday’s Game 5 gave the World Series to the Los Angeles Dodgers and ushered in the start of baseball’s winter. Every offseason is loaded with uncertainty, but there are deadlines and mile markers that help guide the way to next spring. Here’s the road map.
Today — Eligible players become free agents
Wednesday night, Walker Buehler threw the final pitch of the World Series while wearing his familiar Dodger blue. As of today, he’s technically no longer a Dodger. Players with expiring contracts become free agents the day after the World Series ends, meaning Max Fried is no longer a Brave, Alex Bregman is no longer an Astro, and Juan Soto’s one year with the Yankees is officially over. Here’s Jim Bowden’s early look at the biggest names on the market.
Just because these guys are free agents, though, doesn’t mean the market has truly opened. Teams have a five-day window in which they have the exclusive right to negotiate with their own free agents (though very little tends to happen within that window). Major league trades are also back on the table — they aren’t allowed from the trade deadline through the World Series — but, again, there tends to be very little action right away.
Next five days — Defining the market
Free agency opens to everyone Monday, but until then, teams, agents and players will be busy further establishing the market.
Contract options
Teams and players have until Monday to decide on contractual options for next season. San Francisco Giants starter Blake Snell, for example, is expected to decline a $30 million player option for 2025, and the Baltimore Orioles will surely decline their team option on outfielder Eloy Jimenez. The St. Louis Cardinals face interesting decisions on veteran starters Lance Lynn and Kyle Gibson, and so do the Tampa Bay Rays with longtime second baseman Brandon Lowe. Yankees ace Gerrit Cole can opt out this winter. He has $144 million left on his deal, which is a lot for a guy who made just 17 starts this season. But he did look good in the second half and in the World Series.
Qualifying offers
The deadline to make a qualifying offer is 5 p.m. ET Monday. This year’s qualifying offer is set at just over $21 million, and players who accept will be under contract for that amount next season. Players who decline will hit the open market with their former teams entitled to draft compensation when they sign elsewhere.
40-man roster cleanup
At the end of this five-day window, teams must remove players from the 60-day injured list, meaning those players will once again count against 40-man roster limits. This usually leads to a few marginal players being put on waivers, and every year a handful of those marginal players end up making an actual difference the following season.
Nov. 3 — Gold Glove winners announced
This is your annual reminder that baseball writers do not vote for the Gold Gloves, so don’t be mad at us if Soto wins one. (Soto, and his minus-5 outs above average, is among the finalists.) Silver Sluggers will be announced roughly a week later, on Nov. 12. Gold Gloves are announced on ESPN, Silver Sluggers on MLB Network.
Nov. 5-7 — General managers meetings
These are not the Winter Meetings. We repeat, these are not the Winter Meetings! The GM meetings happen basically the week after the World Series, and they’re a kind of informal start to the offseason. Some trade talks might get started, but the GM meetings are not the trade and free-agent bonanza that typically happens at the Winter Meetings in December.
Nov. 14 — MLB Awards
Major League Baseball now hosts an All-MLB weekend, which happens in Las Vegas, and among the major announcements and presentations are the All-MLB Teams, the Hank Aaron Awards, the Edgar Martinez Outstanding Designated Hitter, and the Mariano Rivera and Trevor Hoffman Relievers of the Year, and the Comeback Player of the Year.
Nov. 19 — Deadline Day
Two important deadlines hit on the same day this offseason.
Deadline to accept qualifying offers
We’ll probably already have an answer to most of the qualifying offers before this date, but this is the deadline (at 4 p.m. ET) for any player to accept. Only seven players were given a qualifying offer last offseason, and all seven declined. Historically, the vast majority who have gotten the offer have turned it down.
Rule 5 draft protection deadline
If you don’t really follow prospects, this deadline probably doesn’t mean much. If you really follow prospects, then this date means a lot. Minor-league players with significant professional experience must be added to the 40-man roster or else made available to other teams via the Rule 5 draft. Limited 40-man space means teams can’t protect everyone, so talented players buried on one team’s depth chart might get a fresh opportunity with another organization.
Nov. 18-21 — BBWAA awards week
These are the awards you can yell at writers about. The BBWAA awards are announced over four days on MLB Network.
Nov. 18: Rookie of the Year
The National League probably has the two biggest names — Paul Skenes and Jackson Merrill — but the American League has a pretty wide field. Luis Gil and Colton Cowser are probably the AL favorites.
Nov. 19: Manager of the Year
This could be a clean sweep for the Central. Milwaukee Brewers manager Pat Murphy is a favorite in the National League, and two Central Division managers — arguably three, if you really liked the Detroit Tigers — are worth considering in the American League. Steven Vogt of the Cleveland Guardians and Matt Quatraro of the Kansas City Royals are the favorites.
Nov. 20: Cy Young Award
Tarik Skubal is the heavy favorite in the American League, and Chris Sale is the favorite in the National League (though Zack Wheeler is in that conversation, especially if you favor workload).
Nov. 21: MVP
Three weeks after the World Series we’ll find out for sure whether the Fall Classic was a showdown of two MVPs. The Yankees’ Aaron Judge and Dodgers’ Shohei Ohtani are the heavy favorites (though Bobby Witt Jr. and Francisco Lindor are worth mentioning).
Nov. 22 — Non-tender deadline
Broadly speaking, players with less than six years of service time remain under team control as long as their team offers a contract. To non-tender a player is to not offer a contract, and thus let him become a free agent.
Non-tender candidates are usually players who have enough experience to be eligible for arbitration but might not be good enough — in the team’s opinion — to be worth the arbitration raise. MLB Trade Rumors’ annual arbitration projections provide a pretty decent guide to how much an arb-eligible player might earn if tendered a contract. The Houston Astros, for example, will surely pay $15.8 million to keep Kyle Tucker in right field, but are they willing to risk paying $3.3 million to Chas McCormick and $2.2 million to Jake Meyers to have them split time in center? That could be a non-tender discussion.
Dec. 9-12 — Winter Meetings
The main event of every offseason calendar, the Winter Meetings, brings basically every executive, manager and agent under the same roof for four days of meetings and conversations (official and unofficial). The mix of timing and opportunity — bringing key people together after more than a month of planning and evaluating — leads to a flurry of trades and free-agent signings. There are also two smaller events within the main event.
Dec. 10: Amateur draft lottery
Teams find out who is drafting No. 1, and which team just tanked a whole season for next to nothing.
Dec. 11: Rule 5 draft
Unprotected young talent gets picked up by a new team for an essentially free tryout to potentially make the big-league club.
Jan. 9 — Deadline to exchange arbitration figures
Teams and players typically want to avoid arbitration, which is by all accounts an unenjoyable process for almost everyone involved. But when the two sides can’t agree on a deal, they exchange figures and let an arbitrator pick the fairest salary. A lot of deals are usually reached in the days leading up to this deadline.
Feb. 20 — Spring training games begin
This is the start of the exhibition schedule. Players will officially report to spring training a week or so earlier. It’s less than four months away. We just have to get there.
(Top photo: Luke Hales / Getty Images)
