MLB Offseason Calendar: Key Dates to Know

The Twins have holes to fill and key players to either re-sign or replace, so it will be a busy winter for Derek Falvey. From the start of free agency to the start of Spring Training, here is every key date you need to know for the offseason.

Five Days After the World Series: Free Agency Begins

• The World Series will end sometime between November 1 and November 4, 2023. Five days after that, free agents will officially be free to sign with new teams. Teams are allowed to negotiate with players in this five day window, but unless players are re-signing with their current team, they will have to wait until the window has passed to make anything official. Sonny Gray could technically sign with the Twins here, but I wouldn’t hold your breath.
• Player and club options must also be officially exercised by this date. Max Kepler has a team option for $10 million and Jorge Polanco for $10.5 million. You can expect both of those to be picked up.
• One more for this date: Qualifying Offers must be officially extended as well. As a reminder, the QO is a one-year contract offer (worth about $20 million this year) that provides the former team with draft pick compensation if a free agent offered the QO signs elsewhere. Sonny Gray will receive this from the Twins. Players who receive the QO have until November 14 to decide if they will accept or reject the contract.

November 15: Roster Protection Deadline

• In order to protect players from the Rule 5 Draft, teams must add players to the 40-man roster by November 15. Top prospects that need to be protected include Emmanuel Rodriguez, Austin Martin, Jair Camargo, Yunior Severino, and Jose Salas. However, there’s always a few surprises added like Brent Headrick and Casey Legumina last offseason.

November 17: Non-Tender Deadline

• This often goes hand-in-hand with roster protection as teams are often dropping players from their rosters in order to add the players they wish to protect. However, actual deadline is two days later. Non-tender candidates for the Twins could include Nick Gordon and Jordan Balazovic, both of whom are out of minor league options and don’t have a clear role on the Major League roster. Kyle Farmer could be non-tendered as well with his 2024 arbitration salary estimated to be around $6.6 million, which may be a bit too pricey for a 33-year-old utility player when the Twins have plenty of infield depth. Of note: Jordan Luplow, Jose De León, and Andrew Stevenson were already outrighted and all three elected free agency.

December 3-6: Winter Meetings in Nashville

• There’s typically a flurry of moves in the winter meetings, where teams’ top baseball execs gather to talk trades and free agents come to meet with teams. The winter meetings were eventful last year, with Jon Heyman’s infamous “Arson Judg” to the Giants mishap taking center stage. Every deal won’t happen during the Winter Meetings, but the groundwork for future moves is often laid here, such as the Twins’ Pablo Lopez for Luis Arraez swap last year.
• The Winter Meetings will conclude with the Rule 5 Draft, where teams will have the chance to select other teams’ players who aren’t on the 40-man roster. Players who signed at 18 or younger must be added to the 40-man within five years to be protected, while ones who signed at 19 or older have to be added within four years. Players who meet that criteria but aren’t added by the November 15 deadline are eligible to be selected by another team, and must remain on that team’s big league roster for the entire season or else they will be returned to the original team.
• With the Twins competing for a World Series title, it’s unlikely they will waste a 26-man roster spot on an unproven, inexperienced rookie, but crazier things have happened. In similar positions to the Twins, the Brewers took Louie’s brother Gus Varland in the R5 Draft last season and the Phillies took Noah Song, though Varland was bad and Song was eventually returned to the Red Sox. The Twins have had a couple of R5 hits in the past, acquiring both Johan Santana and Ryan Pressly through the draft.

January 12: Arbitration Figures Exchanged

• For any arbitration-eligible players that haven’t agreed to a contract, the team and the player will exchange what each party feels the salary should be for the 2024 season. The case will then go to an independent arbitrator (taking place sometime in February) who will hear both sides’ cases and decide between one of the two numbers, not somewhere in the middle. However, teams and players can still negotiate right up until the start of the hearing. Twins players eligible for arbitration this year include Caleb Thielbar, Kyle Farmer, Willi Castro, Ryan Jeffers, Alex Kirilloff, Jorge Alcala, and Nick Gordon.

January 15: International Signing Period Opens

• Each team is given a certain amount of money to spend on international prospects. The amount corresponds to whether you receive Competitive Balance Round picks in the amateur draft, with the Twins being in the group with the second most money to spend, $6,520,000. In order to be eligible to sign with a team, a player must be at least 16 years old prior to September 1, 2023 and reside outside of the US, Canada, or Puerto Rico. Most of the bonus pool money will be spent immediately
• With many of the players being 15 or 16 years old, there is truly no way to tell how any of these players will develop. There’s no better example of this than this year’s likely NL MVP, Ronald Acuña Jr., who signed for a measly $100,000 in 2014 and has become one of the best players in baseball. They're the biggest lottery ticket in baseball.
• The vast majority of signees will come from the Dominican Republic and Venezuela, though there are always a few from outside of those areas as well. (May I interest you in our resident German, Max Kepler, who signed for $800,000 in 2009)

February 12: Pitchers and Catchers Report to Spring Training

• Flash forward to the future. Our long national nightmare is over. And now our watch has ended. It’s baseball time. No more theoretical lineups and player improvements, just the real thing. I legitimately can’t wait. Anyway, here’s a helpful tracker if you want to feel sad for a minute.

There it is! The nice thing about the baseball offseason is that there are several events going on throughout the winter which gives us stuff to get excited about. There tends to be a lull in January, but Derek Falvey has a history of making some big moves around that time, which is always appreciated from a content perspective, if nothing else. As we approach each of these deadlines, I’ll have breakdowns of all the important decisions the Twins will have to make along the way.