Laying Out the MLB Offseason Calendar

The World Series is already underway, which means the playoffs are almost over, and the offseason is just around the corner. For me, it’s already well underway and always on my mind.

That’s the reality for those of us who follow the Pirates, so it’s always important to have an idea of what’s to come and when, as baseball’s offseason starts hot and heavy once the World Series ends, with important dates to have circled one after another.

With that in mind, I thought I would cover those for you—so you don’t have to go tracking them down yourself—with important context when it comes to the team and just what every date exactly means for them.

Oct. 15^th – Final Day of the Article XX(D) Free Agency Period

This already passed, but I wanted to at least mention it. Article XX(D) Free Agency is what allowed Justin Bruihl, Domingo Germán, Billy McKinney, Edward Olivares, Ryder Ryan, and Jake Woodford to hit the market earlier than your run-of-the-mill minor league free agents (more on them in a bit).

These six were outrighted during the season, and they accepted the assignments as opposed to electing free agency—a right they all possessed as players who had previously been outrighted (Bruihl and Ryan) or with more than three years of service time (Germán, McKinney, Olivares, and Woodford).

Certainly not monumental moves, but it still helps to understand why and how they happened.

Oct. 30^th, 31^st, Nov. 2^nd, or 3^rd: Eligible Players Become Article XX(B) Free Agents

The next several deadlines are fluid, as they are dependent on when the World Series ends—and these are based on the original playoff schedule that was announced back in August.

The team has a longer list than usual—as they didn’t trade off veterans at the deadline this season—with Jalen Beeks, Ryan Borucki, Aroldis Chapman, Yasmani Grandal, and Andrew McCutchen all slated to hit the market come early November.

For what it’s worth, this is also the first day of the offseason trades can be made between Major League teams, as well as the beginning of the Quiet Period, in which these players can’t be contacted or signed by interested suitors—outside of the prior teams, that is.

Nov. 1^st, 2^nd, 4^th, or 5^th: Decision on Marco Gonzales’ option due

There is no one common date for decisions on options, but Marco Gonzales’ specifically is three days after the World Series.

There’s no drama here, as Gonzales barely pitched with the club, while also undergoing surgery towards the end of the season that could keep him out for much of 2025.

The fact the option is for $15 million doesn’t hurt either.

Nov. 2^nd, 3^rd, 5^th, or 6^th: Last day to request waivers on draft-excluded player

I wouldn’t be surprised if this was a first for you, so just what is a draft-excluded player?

Players who are selected to the roster after August 15^th who otherwise would have been eligible for the Rule 5 Draft if not for the selection and had less than three years of service can potentially become a draft-excluded player—but only if they remain on the roster after the Rule 5 Draft. Said players can be released, they just can’t be assigned to the minors—optionally or outright—until 20 days before Opening Day.

Players fitting the bill here are Billy Cook, Isaac Mattson, and Nick Yorke. For reference, Hunter Stratton was a draft-excluded player last offseason, which is likely one of the reasons he was non-tendered as opposed to ran through waivers.

Nov. 3^rd, 4^th, 6^th, or 7^th: Most everything…

This is obviously a bit cheeky, but five days after the World Series ends is really when the offseason kicks into high gear, and it’s probably best to break the deadline into smaller parts.

Last day to tender Qualifying Offers: Even though the Pirates aren’t offering any of their pending free agents $21.05 million to stick around, I at least wanted to mention this was part of the proceedings.

Domestic Reserve List limit changes: A limit that was at 165 all season, the threshold increases to 175 until Opening Day of the Minor League season.

End of the Quiet Period: Even though free agency in baseball is more of a slow burn than the fireworks show we see in other leagues, players are technically allowed to start signing at this point.

Players must be reinstated from the 60-day injured lists: This includes injured players in both the major and minor leagues—as well as the Full Season injury designation—and obviously is a bigger deal as far as the 40-man roster is concerned.

At this point, the Pirates will have six players who would need to be reinstated: Ben Heller, Daulton Jefferies, Dauri Moreta, Johan Oviedo, Endy Rodríguez, and Hunter Stratton. Since the club typically doesn’t have a lot of free agents, they always have to make space for these players; however, barring any unforeseen moves, there should be enough room on the roster at this point to add everyone back without making any corresponding moves.

Last day to outright potential Minor League free agents: Many players get run through waivers at this point, as teams need to make room for all those they placed on the 60-day IL throughout the season, with many ending up getting assigned outright to the minors. However, this is the last day a player who would otherwise qualify for minor league free agency can be outrighted to the minors. While it’s a tad confusing, effectively, what does it mean?

As the next step shows, this is the time when eligible minor league players hit free agency, which can be more lucrative than yearly contract renewals. If a player who could have had that opportunity gets outrighted after the fact, they must be signed to a contract for the subsequent season before they are allowed to be outrighted.

For example, in the 2021-22 offseason, the Pirates outrighted Michael Perez in mid-November, after the minor league free agency deadline but before the tender deadline—another important part of this equation, as every player has a contract commitment at that point—but not before signing him to a deal for 2022 at $750,000 in the majors and $350,000 in the minors, a perk of sorts for being outrighted when he was.

This offseason, could that mean that Alika Williams—a player who has not served enough time in the minor leagues (seven seasons) to hit free agency—sticks around a little longer over someone who has (Isaac Mattson, just to name one example)? It’s possible, as there is a little more leeway with a player like Williams.

Moving up the tender deadline from December 2 to the last Friday before Thanksgiving—as they did during the last CBA negotiations—made this discussion less important than it was in the past, as less time between the two dates means less of a need for the necessary roster spots.

Eligible players become Minor League free agents: The Pirates have 22 players slated to hit free agency. I’ll cover the whole list in another post before the deadline, but some highlights include Malcom Nuñez, Aaron Shortridge, and Eddy Yean.

November 4^th-7^th: GM Meetings in San Antonio, Texas

While it’s not on the level of the Winter Meetings in terms of transactions, it at least offers the opportunity to get the hot stove warmed up.

November 19^th: Last Day to Outright Injured Players, Along with Setting Reserve Lists

During the season, teams are not allowed to assign injured players to the minors—they must be released. Starting the first day after the season, there’s a short window in which they can be assigned to the minors, ending on the 19^th.

Heller, Jefferies, and Stratton (but only due to his injury status) are injured players who could be in jeopardy of losing their roster spots, but all three would have otherwise reached minor league free agency, so they likely wouldn’t be let go at this point in the offseason anyway.

This is just something to consider, given the allowable timelines.

As for setting the Reserve Lists, this is what is more colloquially known as the Rule 5 deadline. It’s one and the same—protecting eligible players from the Rule 5 Draft. Given a shortened 2020 draft and no international signing period, the team has quite a sparse field to choose from this offseason, with Yorke and Cook already getting their spots and no other players likely to be protected. I covered the list of eligible players already, if you need a refresher.

Also receiving less press, but still part of the same deadline, is setting the 38-player Triple-A Reserve List, which protects players from the Minor League portion of the Rule 5 Draft. The Pirates always gain and lose a handful of players as part of this process.

November 22^nd: Tender Deadline

This is the last opportunity for teams to drop players from their roster—no questions asked—with no further contractual or monetary commitments. Otherwise, after tendering a player a contract, they are tied to them for the following season.

Tendering players are often viewed only through the scope of arbitration—tendering or non-tendering an arbitration-eligible player—however, every player gets tendered a contract, and pre-arbitration players get non-tendered, just not as often. Just last offseason, it happened with both Osvaldo Bido and the aforementioned Hunter Stratton.

December 8^th: Final Day to Outright Players Before the Rule 5 Draft

Roster space is often needed in case a team wants to make a selection in the Rule 5 Draft, and this is the last opportunity that a player can be placed on waivers and subsequently outrighted before that.

Remember, a player need not be designated for assignment—or even have it announced—to be placed on waivers, so when this year’s Yerry De Los Santos or Vinny Capra get outrighted or claimed without warning, don’t be surprised. You now should know better!

December 10^th: Draft Lottery

Instituted as part of the 2022 CBA negotiations, this will be the third draft lottery. That’s important because as part of the new system, non-payee clubs under the revenue-sharing system cannot finish in the lottery two years in a row, meaning the moribund Chicago White Sox can’t pick higher than tenth this time around. They aren’t alone, however, as the Oakland A’s—who as a payee team can’t pick in the lottery three consecutive years—also cannot pick higher than tenth. Given their respective records, the White Sox are guaranteed to be pick tenth, while the A’s will pick eleventh.

In turn, each team’s odds—16.5 and 10%, respectively—get allocated evenly to everyone else.

The Pirates, who finished with the eighth-worst record in the league, start with a 3.9% chance at the first pick. Their share of the odds for the two ineligible teams bumps their total chances up to 5.3%.

The Pirates will pick no lower than fourteen in the 2025 draft.

December 11^th: Rule 5 Draft

One of the hottest dates on the baseball offseason calendar—taking place on the final day of the annual Winter Meetings, which start on the 7^th in Dallas, Texas—has the Pirates slated to pick eighth overall, as no lottery is in place here.

The Pirates ceded their turn in the draft last season.

December 15^th: End of the Current International Signing Period

This is the final day to sign eligible players for the 2024 International Signing Period, with a month off until the next period starts.

Right now, the Pirates have $109,800 left to spend—at least before the Raimi Mueses signing—which is significantly less than they left themselves last year. They ended up spending most of it though, so it’s possible they still have their eye on someone.

If for some reason it’s not clear, the Pirates lose out on the ability to spend that money if they don’t by December 15th.

January 10^th: Arbitration Exchange Date

The Pirates have an eight-player arbitration class, with the following estimates from MLB Trade Rumors:

David Bednar: $6,600,000

Bryan De La Cruz: $4,000,000

Connor Joe: $3,200,000

Bailey Falter: $2,800,000

Joey Bart: $1,800,000

Dennis Santana: $1,800,000

Colin Holderman: $1,400,000

Ben Heller: $1,000,000

Of course, there’s a long way to go until it reaches this point, with settlements and potential non-tenders changing the landscape, but if contracts can’t be agreed to and it makes it to January, this is when the sides exchange salary figures. At that point, as a file-and-trial team, the Pirates don’t negotiate one-year deals after submitting their figures.

It’s important to note that the sides don’t know where each is going to submit, so it’s not worth your while getting disgruntled over the potential difference of a few hundred thousand dollars—the process is more complicated than that.

January 15^th: Beginning of the 2025 International Signing Period

The last significant date on the calendar before we really start to think about pitchers and catchers, is January 15th is the new July 2nd.

According to Ben Badler of Baseball America, the Pirates will have $6,908,600 to spend in 2025. It’s important to remember that despite hiring a new Director of International Scouting, most of these funds are already promised to the previous regime’s signing class.

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I hope I didn’t miss anything, but that should be the most comprehensive calendar you read this offseason.

Leave any questions in the comments and I’ll be sure to address them!

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