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I simulated the 2023-24 Yankees offseason

In this world, the Yankees made one big splash, but it was a slow winter anyway.

San Diego Padres v San Francisco Giants Photo by Ezra Shaw/Getty Images

Every year, Max Rieper from Royals Review hosts a gathering of reasonably intelligent baseball fans to simulate the MLB offseason over a single weekend. For the last five years, the task of filling the Yankee GM’s shoes has fallen to me, and I stared down a roster as inflexible as any in the game.

Here are the ground rules:

  • We rewind to the end of the regular season. The assumption is that your GM has resigned and been replaced. The new GM is free to set their own organizational philosophy.
  • We’re not concerned with the 40-man roster.
  • Players with no-trade clauses cannot be traded (this includes players with 10-5 rights). Players with limited no-trade clauses can be traded.
  • Minor leaguers can be traded, but must be specified. No Players to be Named Later. Cash may be dealt, but the amount must be specified.
  • You are free to frontload or backload contracts, although player preferences are for contracts not to be backloaded. Anything ridiculous will not be accepted. You can offer player, club, mutual, and vesting options.
  • Top offer will typically be taken, although there may be exceptions if a player has a preference on where he wants to play (big market over small market; older vet may want to play for a “winner.”)
  • I am not going to negotiate long-term deals for players who are not free agents.

Max does incredible work as the sole man behind the curtain, and deserves a shoutout for one of my favorite parts of the offseason. We will need to get him some help before next season.

My front office team of Peter Brody, Madison Pavich, and Esteban Rivera helped design the offseason strategy, build trade packages, advise on free agent offers, and scout opposition rosters for the best possible moves. They spent their entire weekend glued to a Slack channel, so thank you to those three for that. And lastly, thank you to Evan for not being too weirded out when I started going sicko mode on Saturday afternoon as the simulation took off.

Now, on to the strategy.

In previous years, I’ve given a blow-by-blow of the moves made, but I think that that’s less interesting than the thought process and the obstacles encountered while executing that process, because it reveals something that’s just fundamentally broken about the New York Yankees roster.

The Yankees have the same number of no-trade clauses for players in their 30s (five) as they do pre-arb players — and two of those pre-arb guys are in the bullpen, where the least amount of payroll is committed anyway. This is an old team, and it’s a team without much flexibility. Giancarlo Stanton can’t move anywhere, DJ LeMahieu’s decline in skill paired with an NTC means you can’t really dump him off the way we would for a league-average, aging utility guy. Aaron Judge and Gerrit Cole aren’t going anywhere nor should they, but it’s these other “locked in” players that make it really hard to make the flexible choices to surround an MVP and likely Cy Young winner with elite talent.

The budget I was set by Max was “?”, reflecting the uncertainty around what this team can and should and will do. You can’t strip it for parts, both because of those NTCs and because you can’t afford to lose any more of Judge and Cole’s primes. You can’t swell up and just sign everyone because those payroll commitments and CBT penalties are real concerns of the front office, even if I take them less seriously. Eventually as a team we decided to set the budget at $300 million.

That’s more, before CBT penalties, than I think Hal Steinbrenner would spend on the club (he confirmed as much yesterday), but it’s not so much that we get stupid carried away. As it turned out, we actually came in quite a bit under that number, finishing with a 26-man roster cost of $246 million. Adding in the costs of the remaining 40-man roster spots plus the benefits, you’re looking at a steady payroll, somewhere right around $275 million.

Note: Please excuse player name typos in the images of the hasty messages. Time was of the essence in the simulation.

To start with, we cleared $15 million or so in payroll commitments with a blitz of nontenders:

These eight guys, plus Albert Abreu, freed up some immediate constraints. The replacements were easy to find — instead of Domingo Germán, we turn to swingman and out-of-options Yoendrys Gómez at a quarter of the price. Instead of Billy McKinney or Jake Bauers, let’s see what Estevan Florial can do with a full season as a backup outfielder, and one who can actually play defense.

This set the stage for a minor, but key, trade:

Harrison Bader was a free agent, and with uncertainty around when Jasson Domínguez will be able to play center field full time, we needed a cheap, controllable player who can man center until the Martian returns, but isn’t going to cost the team anything by being moved to the fourth outfield role. Jake McCarthy fits that bill perfectly, comes on a league-minimum salary, isn’t a free agent until 2029.

I think there’s upside in the bat — he doesn’t strike out much and his 98th-percentile speed means if the Yankees can engineer some contact he works well in the bottom of the lineup. In a lot of ways, it’s similar to the trade for Andrew Benintendi, except McCarthy costs less, is under control for longer, and can easily shift to a bench role in May or June, whenever Jasson X is back in action.

Next up, the Nationals inquired about minor league depth, a trio of players far enough down the org depth chart that I was fine to take a flier on an MLB reliever — the Yankees, pretty famously, are good at taking other team’s low leverage guys and making them high leverage.

The Nationals GM, who I imagine will pop up somewhere in the comments, is our favorite little Adderall bunny, bouncing around in the DMs of every single GM and inquiring about virtually every player in the league. Jordan Weems boasts a lively fastball and above-average strikeout rate, the trick is going to be figuring out how to limit walks. He’s a depth piece, not going to take innings set out for Clay Holmes or Jonathan Loáisiga, but I trust Matt Blake and the team to get something out of him.

Now, the big one.

Juan Soto was as due to be traded in this sim as he is in real life. Given the constraints of the roster, it was going to be a challenge to land Shohei Ohtani, and the free-agent premium tacked onto this exercise (more on that in a minute) cooled my desire for the mercenaries on the market.

This is an overpay, please do not yell at me in the comments — you will anyway.

The big sticking point in this one is the inclusion of all three pitching prospects. After his 2023, I think Drew Thorpe is as close to untouchable as anyone in the system can be. Still, I beg your understanding due to a variety of factors.

One, this is Juan Soto, he is perfect for the Yankees, and the Yankees have him and 29 other teams do not. Two, this is Juan Soto, he is perfect for the Yankees, and the Yankees have him and 29 other teams do not.

Third, these were the premiums on the highest free agents:

When you’re staring down the barrel of 15 years for Shohei Ohtani, three pitching prospects, an outfielder with swing-and-miss questions, another far far away, and a catcher for a 160 wRC+ left-handed outfielder start to make a whole lot of sense. Maybe we could have dabbled more for Cody Bellinger or Jung-Ho Lee, but would anyone rather have them and Will Warren than Juan Soto?

The immediate reaction to this trade was bifurcated. Four GMs immediately, privately, texted me what a steal it was given the context of the sim tax, while a quintet went into the public group chats to bemoan how the Yankees were hosed and won’t someone think of the combined years of control?? That one of the GMs did both made me think that this was less of a sim of baseball and more one of Congress, where elected leaders will get in front of a camera and be all too eager to whip out a catchy soundbite that plays to the base, and then immediately change tack once they’re in a private room with colleagues, who “know the game.”

I’ve long thought one of the great diseases of our time is how the media covers sports like politics, and politics like sports, but if that attitude has netted our fictional Yankees Juan Soto, maybe in this example, it plays to our benefit. This is Juan Soto, he is perfect for the Yankees, and the Yankees have him and 29 other teams do not.

The possibilities here are extraordinary. The Yankees will start the season without one of baseball’s best prospects, a centerfielder at that, and will still boast the best outfield in the game. Do you bat Soto second, giving Aaron Judge a real opportunity to approach the kind of RBI totals the Yankees haven’t seen since the Iron Horse was tasked with driving home Babe Ruth? Do you keep Judge in the two-hole, and see how close to .500 we can push the game’s best hitter’s OBP?

With the Soto business concluded, we focused on two final targets: Yoshinobu Yamamoto and Bobby Witt Jr. The bidding for Yamamoto, who in real life I think is an absolute star and expect to be better than Masahiro Tanaka, escalated beyond my final offer of 14 years, $475 million. That deal would likely mean, barring the opt-outs I had planned after years three, five, seven and 10, Yamamoto would spend his entire career in pinstripes. The extra year, as the Yankees often do, was critical to lowering the AAV to an acceptable level, but after you set a final offer, it is final. Maybe it was silly to lose Yamamoto over $5 million a year, but by the time that decision was made we had moved on to other things.

As for Witt, the Soto deal may have been our undoing. Kansas City made the star shortstop available in a shoot-the-moon offer, and given the positional advantage and fact he doesn’t have a torn UCL, Witt was exactly the type of player you offer someone like Jasson Domínguez up for. The deal showed promise but eventually fell apart since the core pitching depth in the minors had already been spoken for.

We signed two players to MiLB contracts, Clint Frazier and Miguel Andújar. I don’t expect anything to come of either, but the joy of having Gerrit Cole and Juan Soto, while also having both Andújar and Frazier, should not be lost on any Yankee fan who has been on Twitter since 2018.

Full freight, here is our 26 man, Opening Day roster:

Now, we run into this problem that we’ve talked about since August. We have a capable center fielder and will have closer to a full season of the Martian. We’re counting on Anthony Volpe to take a step forward offensively and Anthony Rizzo to not play two months with a concussion, and Aaron Judge to not have one of the freak injuries that, as truly great a player as he is have happened now three times in a seven year career.

We’re counting on Carlos Rodón to remember how to pitch again and Giancarlo Stanton to remember how to hit again and neither Gerrit Cole nor Michael King’s UCLs to explode when every single time they throw a pitch it carries that risk. Even with Juan Soto, there are so many question marks with this roster and so many ways things can go just wrong enough, in an always terrific division, that the Yankees find themselves on the outside looking in.

There’s no single move that the Yankees can make that would make them division favorites, and the financial and contractual constraints on the roster make it increasingly difficult for the kind of multi-move offseason that delivered a world championship in 2009. It’s this fear that makes me so cautious about the remainder of Judge and Cole’s prime. As they get older, as DJ and Stanton’s contracts go further underwater, that inflexibility is going to stay. This simulated Yankee squad, if guys can stay on the field, may just be a playoff team, but the work facing the real team may be even harder.