How the Yankees’ worst contracts are weighing on their offseason

Here is an exercise I go through each year: I pretend baseball has an amnesty program — essentially a team could release any player and be free of his contract while receiving nothing in return. Who would go?

I do it annually as an antidote to amnesia, which is rampant at this time of year. There is nothing lauded quite like spending big in the winter, even with evidence that naming offseason champions based on that is so often a losing strategy.

It is what makes the Mets’ shopping spree last offseason so impressive. They signed five major league free agents — Mark Canha, Eduardo Escobar, Starling Marte, Adam Ottavino and Max Scherzer — and did not have any of the contracts go rancid. Might they ultimately have some regret about the two years at $86.6 million still due to Scherzer? Perhaps. Might they prefer to spend the $10 million still due Escobar in a different fashion moving forward? Maybe. But it isn’t as if they have received nothing for the dollars spent or that they are sitting on a disastrous pact.

Conversely, the Marlins, a team without Steve Cohen’s largesse to get spending wrong, signed two major league free-agent contracts last offseason, and both went terribly. Avisail Garcia (four years, $53 million) and Jorge Soler (three years, $39 million) combined for 0.0 Wins Above Replacement (Fangraphs).

There were 11 nine-figure free-agent deals signed last offseason, and I am fairly certain if there were an amnesty program, a minimum of four teams would use it on one of those deals: the Rockies with Kris Bryant (seven years, $182 million), the Tigers with Javier Baez (six years, $140 million), the Red Sox with Trevor Story (six years, $140 million) and the Phillies with Nick Castellanos (five years, $100 million). Those teams still have time to see benefits from those contracts, but I assume all of them would rather be out than see whether the deals have upside.

Nevertheless, no one should be surprised if the total dollars spent between now and the end of the Winter Meetings exceeds $1 billion as teams gather for the event for the first time since pre-COVID in 2019. Those meetings also were in San Diego. There was a combined $814 million spent in a three-successive-day frenzy on Scott Boras clients Stephen Strasburg (seven years at $245 million), Gerrit Cole (nine years at $324 million) and Anthony Rendon (seven years at $245 million).

The Nationals probably have the worst current contract in the sport with the four years at $140 million left for Strasburg. In the three seasons since signing the deal, Strasburg has made just eight total starts with a 6.89 ERA. He had surgery for carpal tunnel neuritis in 2020 and thoracic outlet syndrome in 2021 and made just one start in 2022. And there are real concerns about his viability moving forward. The Angels certainly would want to be rid of Rendon, who has played in just 105 total games the past two years with a 97 OPS-plus, and still has four years at $152 million remaining.

I do not believe the Yankees would amnesty Cole. One way to think about the question is: If the player were a free agent today, would he approach, if not exceed, what is remaining on his contract? Cole has six years at $216 million left, and I think Cole would land at least that much in open bidding.

But the Yankees have three players I think they would amnesty (Josh Donaldson, Aaron Hicks and Giancarlo Stanton) and a fourth (DJ LeMahieu) they would have to consider seriously. So for 3Up this week, why don’t we expand to consider those four contracts, particularly in relation to how to think about the Yankees’ quest to retain Aaron Judge? Let’s go in order of money owed:

1. Stanton has five years at $160 million left on his deal, but the Yankees owe $130 million of that with the Marlins obligated to the other $30 million. It is not an onerous amount for a big-market team, especially because Stanton has demonstrated an ability to hit (particularly for power) in the postseason.

Yet, Stanton is a Yankees problem. He was a central figure at the pivotal moment in the recent history of the team.

The Yankees had an ascendant 2017 season. Judge nearly won the MVP with 52 homers. Luis Severino pitched like an ace. And in what was supposed to be at least a bit of a rebuild year, the Yankees went to Game 7 of the ALCS before losing to the Astros. They left that series believing they had a young core (Judge, Severino, Gary Sanchez, Jordan Montgomery and Miguel Andujar, with Jackson (Clint) Frazier and Gleyber Torres on the come) to contend for years. Plus, they thought they had as good a chance as any team at landing Shohei Ohtani.

But at about this time five years ago, the Yankees were made aware they were not even among the seven Ohtani finalists (all of those teams held spring training in Arizona and five were on the West Coast). Within the week, the Yankees had spun to acquire Stanton from the Marlins.

At that point, there were 10 years at $295 million left on Stanton’s contract (with Miami paying $30 million of that). In real time, the Yankees felt this was a bit of thievery — getting the reigning NL MVP coming off a 59-homer season for two lottery-pick prospects (Jose Devers and Jorge Guzman) plus actually having the Marlins pay more than 10 percent of the remaining contract. But after Stanton had used his no-trade clause to reject trades to San Francisco and St. Louis, there were not many options left for where to move as much of the contract as possible — a move that has proved valuable to the Marlins even as the two prospects failed to hit.

Meanwhile, Stanton has contributed to three problem areas for the Yankees:

• The length and dollars in the Stanton deal have chilled Hal Steinbrenner from approving financial outlays elsewhere.

• The inability of Stanton to stay healthy (a combined seven IL stints in the past four seasons) has not only kept him out of the lineup, but also limited how much he can play the field when he is active. Which has jammed up the DH spot.

• His addition contributed to keeping the Yankees a predominantly righty-hitting team.

Taking on Stanton’s 10-year contract came just after the Yankees completed Alex Rodriguez’s 10-year deal, which had the organization’s leaders for a time saying they would never do a deal like that again — not just because of the PED furor and overall controversy but because of how badly Rodriguez broke down physically during the life of the long deal.

Now Judge, who will be entering his age-31 season, appears in line for, at minimum, an eight-year deal. He will be coming off an MVP season, as surely as Stanton once was. And that helps lead to amnesia about the injuries and the worries over how a player the size of Stanton and Judge will age, when there are not a lot of precursors for comparison.

With Stanton signed for five more years, it will be harder to protect Judge with regular DH days. It will continue to be hard to find left-right balance for the lineup.

I find it difficult to believe any team would give Stanton the five years at $130 million he has left on his deal with the Yankees if he were a free agent. If Stanton cannot play the field regularly, how much better is he than Luke Voit? One grade better? If I had to guess, Voit probably ends up with a one-year deal in the $6 million range. Is Stanton all that different from J.D. Martinez, who will get what? One year at $12 million? For what it is worth, in 2022, Stanton had the same offensive WAR (Baseball Reference) as Martinez and — believe it or not — Hicks. Stanton’s exit velocity average (third-best in the major behind Judge and Houston’s Yordan Alvarez and far superior to Voit’s and Martinez’s) remains elite, so perhaps that would differentiate him enough to get multiple years in the marketplace, but not likely five years at $130 million.

A trade? I have never sensed the Yankees believed Stanton would be amenable to waiving his no-trade clause.

At this point, I would say there is a better chance Stanton follows the path of A-Rod and Jacoby Ellsbury and is released well short of the finish line of his contract than that he plays it out through his age-37 season in 2027 (which is Judge’s age-35 season, by the way).

It is a reminder that — even with better training programs to extend prime years — the Yankees better be comfortable that whatever they pay Judge is really about the first four or five years of the deal and that by the back end they will probably be weighing many of the same issues they currently are with Stanton.

2. LeMahieu has four years at $60 million left. He was coming off a fourth-place and a third-place MVP finish when Steinbrenner determined that the offseason following the 2020 season would be built around retaining him  — as Steinbrenner has determined this offseason is about keeping Judge.

Since then (in his age-32 and age-33 seasons), LeMahieu has needed core surgery following a disappointing 2021 campaign and might need foot surgery after a poor second half in 2022. For most of the first half, LeMahieu was in vintage form, not only hitting, but fielding multiple positions at a high level (he won a Gold Glove Award that way). But even Steinbrenner has conceded he has no idea what the Yankees can expect from LeMahieu for 2023. LeMahieu won’t know whether he needs surgery until January. With or without surgery, there will be mystery around how much the Yankees can count on him.

For luxury-tax purposes, Steinbrenner stretched out LeMahieu’s contract to pay him $15 million per for six seasons rather than $18 million per for four seasons. As things look now, the Yankees would have been better off spending more annually and being closer to the end.

LeMahieu had his best full season of his career in 2019 at age 30, the same age that Judge was for his best season.

3. Hicks has three years at $30.5 million left and also is due a $1 million assignment bonus if traded. Maybe there is not much in common between Hicks and Judge besides the same first name.

The injury-prone Hicks was coming off his best season when the Yankees extended him for seven years at $70 million. As with LeMahieu, the Yankees were fixated on lowering the average value of Hicks’ deal for luxury-tax purposes, and extended to seven years to make his annual value $10 million. If it were four years, the deal would have concluded after last season.

Perhaps the LeMahieu/Hicks pacts should motivate the Yankees to pay Judge more for eight years rather than stretch it out over, say, 10 years — unless they are committed to cutting Judge when he becomes ineffective during the longer deal.

4. Donaldson has one year at $27 million due. It is $21 million for 2023 with a $16 million mutual option for 2024 or a $6 million buyout. I would assume the Yankees are more likely to bring Mike Blowers back to play third in 2024 over picking up their side of Donaldson’s option.

In fact, how would you forecast the chances that Donaldson gets through all of the 2023 season with the Yankees? Is that even 50 percent?

If LeMahieu is 100 percent healthy, I suspect he will be the primary third baseman next year with some combination of Oswaldo Cabrera, Isiah Kiner-Falefa, Oswald Peraza, Gleyber Torres and Anthony Volpe manning the middle infield. Does Donaldson have value as a bench player? Will he be a good soldier if he is a bench player?

The uncertainty about LeMahieu and the limited (non-existent?) trade market for Donaldson could convince the Yankees to hold onto Donaldson. He was very good on defense last year. Could the Yankees sell themselves on the idea that his offense — subpar all year, but a strikeout nightmare late in the season through the playoffs — will be better in his age-37 2023 season? These Yankees have hard-headedly become experts at holding onto a bad idea for a season or two longer than they should (Torres at shortstop, as an example).

Donaldson won the AL MVP in his age-29 season and nearly repeated at age 30. He has had one fully healthy season since, and was on the injured list seven total times in six years. He has played in 615 games since 2017 (Judge’s rookie year). That is six fewer than Brett Gardner, who did not play at all in 2022.

After that one healthy season for the Braves in 2019, the Twins rewarded Donaldson with a four-year, $92 million pact. Again, amnesia strikes at this time of year. The Yankees traded for the final two years last offseason. Less than 12 months later, they would love to have the amnesty program.