THE New York Yankees managed to delay the offseason by a day, but Wednesday’s Game 5 gave the World Series to the Los Angeles Dodgers and marked the start of baseball’s winter. Every offseason is full of uncertainty, but there are deadlines and milestones that help chart the path to next spring. Here is the roadmap.

Today — Eligible players become free agents

Wednesday evening, Walker Bühler threw out the last pitch of the World Series while wearing his familiar Dodger blue. As of today, he’s technically no longer a Dodger. Players whose contracts expire become free agents the day after the World Series ends, meaning Max Frit is no longer a Brave, Alex Bregman is no longer an Astro, and Juan SotoThe year with the Yankees is officially over. Here’s Jim Bowden’s first look at the biggest names on the market.

Just because these guys are free agents doesn’t mean the market has truly opened up. Teams have a five-day window during which they have the exclusive right to negotiate with their own free agents (although very little happens during that window). Major league trades are also back on the table – they’re not allowed from the trade deadline until the World Series – but, again, there tends to be very little action immediately.

Next Five Days — Defining the Market

Free agency opens to everyone on Monday, but until then, teams, agents and players will be busy expanding the market further.

Contract options

Teams and players have until Monday to decide on contract options for next season. San Francisco Giants starter Blake Snellfor example, should decline a $30 million player option for 2025, and the Baltimore Orioles will surely decline his team option on the outfielder Eloy Jiménez. THE St. Louis Cardinals face interesting decisions on veteran starters Lance Lynn And Kyle Gibsonand the Tampa Bay Rays with a longtime second baseman Brandon Lowe. Yankees ace Gerrit Cole can unsubscribe this winter. He has $144 million left on his contract, which is a lot for a guy who has only made 17 starts this season. But he looked good in the second half and in the World Series.

Gerrit Cole can opt out of the remainder of his contract with the Yankees. (Steph Chambers/Getty Images)

Eligible 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 refuse will enter the open market and their former teams will be entitled to compensation when they sign elsewhere.

Cleaning up the 40-man roster

At the end of that five-day window, teams must remove players from the 60-day injured list, meaning those players will count toward the 40-player limit again. This usually leads to a few fringe players being waived, and each year a handful of those fringe players end up making a real difference the following season.

November 3 — Gold Glove winners announced

This is your annual reminder that baseball writers don’t vote for Gold Gloves, so don’t be mad at us if Soto wins one. (Soto, and his minus-5 strikeouts above average, are among the finalists.) The Silver Sluggers will be announced about a week later on November 12. The Gold Gloves are announced on ESPN, the Silver Sluggers on ESPN. MLB Network.

November 5-7 — Director General Meetings

These are not the Winter Meetings. We repeat, these are not the Winter Meetings! General manager meetings take place primarily the week after the World Series and serve as a sort of informal start to the offseason. Some trade talks might get underway, but the general managers’ meetings aren’t the trade and free agent bonanza that typically occur at the December winter meetings.

November 14 – MLB Awards

Major League Baseball now hosts a All-MLB weekend, which takes place in Las Vegas, and among the major announcements and presentations are the All-MLB teams, the Hank Aaron Awards, outstanding designated hitter Edgar Martinez, relievers Mariano Rivera and Trevor Hoffman of the year, and comeback player of the year of the Year.

November 19 — Deadline

Two important deadlines took place on the same day this offseason.

Deadline to accept eligible offers

We’ll probably already have a response to most qualifying offers before then, but that’s the deadline (at 4 p.m. ET) for any player to accept it. Only seven players received a qualifying offer last offseason, and all seven declined. Historically, the vast majority of those who received the offer declined it.

Draft rule 5 concerning the period of protection

If you don’t really track leads, this time frame probably doesn’t mean much. If you really follow up with prospects, then this date means a lot. Minor league players with significant professional experience must be added to the 40-man roster or otherwise made available to other teams via Draft Rule 5. The 40-player cap means teams cannot protect everyone, so talented players buried in one team’s depth chart might get a new opportunity in another organization.

November 18-21 — BBWAA Awards Week

These are the awards you can yell at writers about. BBWAA awards are announced over four days on MLB Network.

November 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 fairly wide field. Luis Gil And Colton Cowser are probably the favorites in the AL.

Jackson Merrill is expected to finish in the top two in NL Rookie of the Year voting. (Harry Comment/Getty Images)

November 19: Manager of the year

This could be a clean slate for the Centrale. Milwaukee Brewers Manager Pat Murphy is one of the favorites in the National League, and two managers in the Central Division – probably three, if you really liked him Detroit Tigers – are worth considering in the American League. Steven Vogt of Cleveland Goalies and Matt Quatraro of Kansas City Royals are the favorites.

November 20: Cy Young Award

Tarik Skubal is the big favorite of the American League, and Chris Sale is the favorite of the National League (even if Zack Wheeler is in this conversation, especially if you prioritize workload).

November 21: MVP

Three weeks after the World Series, we’ll know for sure if the Fall Classic was a showdown between two MVPs. The Yankees Aaron judges and Dodgers Shohei Ohtani are the big favorites (even if Bobby Witt Jr. And Francisco Lindor deserve to be mentioned).

November 22 — Deadline for no call for tenders

Generally speaking, players with less than six years of seniority remain under team control as long as their team offers a contract. Not offering a player means not offering him a contract, and thus letting him become a free agent.

Non-tender candidates are generally players who have enough experience to be arbitration eligible, but who may not be good enough – in the team’s opinion – to be worth the increase in price. arbitration. Annual Arbitration Projections from MLB Trade Rumors provides a pretty decent guide to how much an arbitration-eligible player could earn if offered a contract. THE Houston Astrosfor example, will surely pay $15.8 million to keep Kyle Tucker in the right field, but are they willing to risk paying $3.3 million for Chas McCormick and $2.2 million for Jake Meyers so that they share their time at the center? This could be a no-bid discussion.

December 9-12 — Winter Meetings

The main event of every off-season calendar, the Winter Meetings, brings virtually every executive, manager, and agent under one 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.

December 10: amateur lottery

Teams find out who the No. 1 draft pick is and which team just wasted an entire season for next to nothing.

December 11: draft rule 5

Young, unprotected talent is recruited by a new team for an essentially free trial to potentially join the big league club.

January 9 — Deadline to exchange arbitration figures

Teams and players generally want to avoid arbitration, which is obviously an unpleasant process for almost everyone involved. But when the two sides can’t agree on a deal, they exchange numbers and let an arbitrator choose the fairest salary. Many deals are usually made in the days leading up to this deadline.

February 20 – Spring training games begin

It’s the start of the exhibition calendar. Players will officially report to spring training about a week early. It’s less than four months away. We just have to get there.

(Top photo: Luke Hales/Getty Images)