New York Yankees Offseason FAQs, Free Agency, Arbitration, Dates to Remember

The New York Yankees failed to make the 2023 postseason, something that is unacceptable for the organization. So the work to correct that for the 2024 has already started.

The Yankees appear to be keeping manager Aaron Boone for the 2024 season, but he’ll need to make a chance in his managerial style in order to do so. The Yankees have a handful of veteran players with big-money contracts and a host of players headed for salary arbitration.

That, plus the Yankees are eager to hit the free-agent market for help, and that could mean pursuing Los Angeles Angels superstar Shohei Ohtani, torn ULC and all.

Need to get ready for the Yankees hot stove this offseason? Our FAQ on the offseason walks you through it all.

November TBA

Last day for club to make a qualifying offer to an eligible former player who became a free agent, fifth day after World Series, 5 p.m. EST.

The day after the World Series ends, the work begins. The Yankees have five days to tender qualifying offers to potential free agents.

So who qualifies for the Yankees? They have seven unrestricted free agents — pitcher Luis Severino, pitcher Frankie Montas, utilityman Isiah Kiner-Falefa, pitcher Wandy Peralta, pitcher Kenyan Middleton, pitcher Zach McAllister and pitcher Luke Weaver (per Spotrac.com).

Do the Yankees believe any of them are worth keeping? This year, the qualifying offer is approximately $20.5 million, which is a one-year offer. It is the mean of the league’s top 125 salaries.

Teams make the qualifying offer to prospective free agents in case they lose them because they’ll receive draft pick compensation, either after the first round or after competitive-balance round B.

Last offseason, 14 players were tendered a one-year qualifying offer worth $19.65 million. Two players — Rangers left-hander Martín Pérez and Giants outfielder Joc Pederson — accepted.

Historically, players don’t accept the QO. Since the QO became a thing in 2012, only 12 players of the 124 players offered the QO have accepted, per the New York Post.

Free agents can receive the qualifying offer. If a free agent has previously been tendered a QO, they cannot be tendered another one. Free agents that have changed teams during the season cannot get a QO.

Once a player gets an offer, he has a week to consider it. During that time he can talk with other teams and solicit interest to help them make a decision. But the deadline to accept is Nov. 14 at 4 p.m. EST.

Nov 7-9 — General managers meetings, Scottsdale, Ariz.

The Yankees brass, including general manager Brian Cashman, will be in Scottsdale for these annual meetings. Don’t expect a lot of league business to be conducted during these meetings. But many team leaders will start laying the groundwork for free agency and trades during these meetings.

Nov. 17 — Last day for teams to offer 2024 contracts to unsigned players on their 40-man rosters.

Any players not under contract or under team control for 2024 must either sign a deal with their current team or they can hit free agency. Most of the big names have either made their decisions or signed with their current teams by this point. As noted, the Yankees have seven unrestricted free agents.

Dec. 3-6 — Winter meetings, Nashville, Tenn.

This is it. MLB’s biggest offseason meeting. Everyone is there — owners, general managers, agents and media. Big deals tend to get done here or get done shortly after everyone departs. Everything is on the table, including free-agent contracts and trades.

Dec. 3 — Hall of Fame Contemporary Baseball/Managers-Umpires-Executives Committee vote announced, Nashville, Tenn.

If you’re into getting your favorite retired manager, umpire and executive whose greatest contributions to the game were realized from the 1980-present era then this is your day. The finalists will likely be announced in advance of the selections, which is done by a 16-member committee and not the wider voting bloc of the Baseball Writers Association of America.

Dec. 5 — 2024 amateur draft lottery, Nashville, Tenn.

MLB will determine the draft order of the non-playoff teams in the 2024 MLB Draft through a weighted lottery system, similar to the NBA Draft Lottery. MLB began using the system last year. Oakland, Kansas City and Colorado each have the best chance of securing the No. 1 pick when the lottery is held. The lottery determines the order of the first six picks.

The Yankees have a 0.5 percent chance of getting the first overall pick through the lottery (but as they say, “So you’re telling me there’s a chance?”). If the percentages hold, the Yankees would end up with the No. 16 overall selection. Right? Well, not exactly.

This year, if the Yankees don’t secure one of the Top 6 picks in the lottery then they would drop to No. 26 overall. The same 10-spot drop applies to the crosstown Mets and the Padres. Why? Because the Yankees, along with the Mets and Padres, were over the luxury tax threshold for their 2023 payroll.

Dec. 6 — Winter meeting draft, Nashville, Tenn.

Don’t recognize this? You probably know it better as the Rule 5 Draft. Before the draft, each team must determine which of its non-40 man roster players need to be added to its 40-man roster. This includes:

Players signed at age 18 or younger that have not been added to the 40-man within five seasons of becoming a pro. Players who signed at age 19 or older need to be protected within four seasons.

So who qualifies for the Yankees? Pinstripedprospects.com had a solid list of just some of the players that the Yankees will have to made decisions on before the Rule V Draft. Some, like outfielder Jasson Dominguez and catcher Austin Wells, are already on the 40-man roster and protected.

Players moved to a 40-man roster cannot be drafted. Players that are not moved can be drafted. The draft order is in reverse order of standings. There is a Major League portion (the portion that most fans pay attention to) and a minor league portion.

For teams that draft a player in the Rule 5 Draft, they must pay $100,000 to the player’s club, put him on their 26-man roster immediately and put him out outright waivers if they release him the following season. If he clears waivers, he goes back to his former team for $50,000.

In other words, if you select a player in this draft your team believes that player is ready to help them in 2024.

Last year the Yankees didn’t draft a Rule 5 player, but they lost two in the draft — pitcher Zach Greene (to the Mets, who was returned to the Yankees in March) and pitcher Wilking Rodriguez (who is now with the Cardinals).

Dec. 15 — International signing period closes, 5 p.m. EST.

If MLB teams have any international signing money left over for 2023, this is the deadline to spend it.

In January, the Yankees agreed to terms with at least nine international players, with the most significant agreement being with Cuban outfielder Brando Mayea, as the Yankees paid the No. 9 international prospect $4.35 million in bonus money out of a $5.284 million pool.

2024

Jan. 12 — Salary arbitration figures exchanged.

Perhaps the least fun part of the offseason for teams and players alike. For players that are salary arbitration eligible, this is the deadline for teams and player agents to exchange numbers. Players who have three or more years of Major League service but less than six years of Major League service are eligible. Most teams and players try to reach agreement on a contract before the arbitration deadline, as the process can become acrimonious.

The following Yankees are arbitration eligible — Lou Trivino, Gleyber Torres, Clay Holmes, Jonathan Loaisiga, Kyle Higashioka, Franchy Cordero, Domingo German, Nestor Cortes, Jose Trevino, Matt Bowman, Michael King, Ryan Weber, Billy McKinney, Jake Bauers, Jimmy Cordero, Clarke Schmidt and Albert Abreu.

If the Yankees have to go to arbitration with any of their players, those hearings will be held between Jan. 29-Feb. 16 in Scottsdale, Ariz.

Jan. 15 — International signing period opens, 9 a.m. EST.

The 2024 international signing period begins. Players eligible to be signed are Player resides outside of the United States, Canada or Puerto Rico and has not been enrolled in high school in any of those locations within the past calendar year. The player is at least 16 years of age or will turn 16 years of age prior to Sept. 1 of the current signing period.