The Tuesday Discussion: Big Contracts and Trades

June 17, 2025

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This week we asked our writers to respond to the following:

The Red Sox just traded Rafael Devers, essentially a DH on a long and expensive contract, to the San Francisco Giants. 

Over the years, through different management teams, the Red Sox have been able to unload a number of big contracts on other teams.  (Carl Crawford, David Price, and Adrian Gonzalez are three such examples.)

Why do the Yankees seem unable to rid themselves of the big expensive mistake contracts they sign players to?

Here are their replies...

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Lincoln Mitchell - This is a very important question because it speaks to a structural problem with the Yankees. Since 2010, ten teams have won at least won World Series. The Yankees are not among them. Yet, uniquely among all teams, the Yankees have a public line that they have to win the World Series every year. The problem with that line is that it never allows the team to rebuild, reload or whatever you want to call it. Getting rid of famous players with big contracts is central to reloading or rebuilding, but it also signals giving up in a given year or two. The Yankees refuse to do that so they end up not being able to move contracts for fear of signaling they are giving up.

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Ed Botti - I believe the primary reason is the person moving those contracts, for the most part, was not the person that acquired the player. For example, Dave Dombrowski acquired Price and Brian O’Halloran traded Price, Theo Epstein acquired Crawford and Ben Cherrington traded Crawford. To dig a little further Josh Becket was acquired by Epstein but traded by Cherrington, Mookie Betts was signed by O’Halloran but traded by Chaim Bloom, Xander Bogaerts was signed by O’Halloran and left unsinged by Bloom.

One exception in your named players is Adrian Gonzalez. He  was acquired by Epstein and also traded by Epstein, but was a part of the Beckett, Crawford deal with the Dodgers.

See a pattern?

I can go on, there are more examples throughout the entire league of star players acquired by one administration and traded by a successor administration.

I have said this for many years now, the Yankee GM, despite making some excellent moves over the years, and some not so excellent moves over the years, has exhibited a degree of stubbornness and obstinacy, IMO. In other words, he doesn’t like to admit mistakes.

Therefore if you have a obstinate GM that has been in charge for 27 seasons, you end up with the current Yankee static contract situation, while other organizations remain flexible.

Just another reason why a change at the top has been needed for quite some time. That is not a knock at anyone. Sometimes, change is needed to balance things out.

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James Vlietstra - There’s a few layers to this. Part of it is that they hold onto the players until they have little to no value. The other thing probably comes down to pride. Cashman likes to be known as the smartest guy in the room. So if he makes a trade that is viewed as a Yankees loss he’d not be pleased. Sometimes it’s not a bad idea to let others think they got the better of you. 

For example if another team was willing to take on Stroman if the Yankees paid $10M but Cashman only wanted to pay down $7M, pay $11M and get a prospect or IFA money.

The Yankees should have a major financial advantage over every other team but they refuse to use the advantage to the fullest extent. 

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Derek McAdam - I think with several of these examples listed, the Red Sox were able to unload them by the time they turned 32, where they still have some trade value. Plus, these players were all having good seasons when they got traded. The Yankees have found themselves sometimes signing players to long-term deals as they are turning 30 and Brian Cashman has too much patience sometimes, especially when it comes to the higher-paid players. 

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Paul Semendinger - The Red Sox won the Devers trade. Easily. Absolutely. Devers can't play the field. He is signed until 2033. He's going to make about $31-33 million a year through 2033. The Red Sox just got out of a terrible contract. And, amazingly, they didn't have to eat any of the money. At all. Not a dime. If all they received in the trade was a non-prospect in Single-A they would have won the trade. The key was moving a player on a terrible contract and who was also becoming a problem within the organization. And that's what they did.

Why can't the Yankees ever do this? Maybe they're stubborn. Maybe they're not creative enough. Maybe Brian Cashman never wants to admit he made a mistake. Maybe they always think something will work out and a washed-up player will be great again. I have no idea why the Yankees can't make trades like this.

Giancarlo Stanton had a gigantic postseason last year. His contract only runs through 2028 and for tons less money than Devers' contract. The Yankees couldn't find anyone who might have been interested in that contract? (I know about the No Trade Clause, but my experience there is that a NTC is used as a way to sweeten the deal for the traded player.)

In short, I think the Yankees could trade away bad contracts, but they simply do not. Whatever the reason, they then use the contract they can't move as a way to say, "We can't get Player X because we already have such a large payroll."

If I owned the Yankees, I'd ask Mr. Cashman to explain how the Red Sox seem to be able to do this time and again while I'm paying good money after bad for fading one-dimensional players that I'm stuck with seemingly forever.

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Tim Kabel - I believe the Yankees could rid themselves of these bad contracts, but, they choose not to. I think Brian Cashman is extremely reluctant to admit that he made mistakes. Perhaps he is also afraid of what he might get back in return. Instead, what we have seen is the Yankees simply getting rid of players like Josh Donaldson and Aaron Hicks. They were able to trade Joey Gallo to the Dodgers but, he did not have much time left on his contract when they made the deal.

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Cary Greene - I just want to start off by admitting that my head is still spinning in the aftermath of the recent Red Sox - Giants blockbuster trade which not only occurred a full six weeks in advance of MLB's Trade Deadline, but also happened to give the Giants an All-Star with a middle of the order bat in exchange for virtually nothing of value. The Giants shipped a terrible lefty starter up to Boston (Jordan Hicks), a below average reliever (Kyle Harrison), a decent prospect (the number four prospect in the Giants MiLB system -James Tibbs) and a bit Minor League righty (Jose Bello). It certainly wasn't much to give up at all for a player with a bat like Devers possesses, so let's start this conversation off with me pointing out that the Red Sox lost this trade badly and them's just the facts folks! They very clearly should have waited until the Deadline as they very likely could have extracted more value from a desperate team with room on the books to absorb the contract Devers is still owed. 

Judging the deal through the lense of BaseballTradeValues.com, the Red Sox parted with negative $40.3 MTV and received back $1.9 MTV, so the trade can be seen as anywhere from a win for the Sox to a fairly even deal, especially if the production Devers will deliver to the Giants is framed by the fact that he's only a one way player. Sites like BTV would have us believe that the acquiring team (Giants) slightly overpaid - but that is very far from the truth as there have been far few sellers at the Trade Deadline ever since the expanded playoff format was introduced. 

While Devers is a sunk cost, "worth" negative $40.3 MTV (due to the roughly $213.6 million left on the 10-year deal he signed in 2023), the Red Sox rid themselves of the contract and more importantly from their perspective, the player....to a team who's lineup has been devoid of a power hitter since Barry Bonds cleaned out his locker full of HGH elixirs, tonics and creams - after his career ended in a cloud of controversy. Suffice it to say that the Giants coveted Devers and they are rolling the dice on Devers, believing that his solid player comps, health history and strong track record of offensive production make him an ideal fit for the middle of their lineup for many years to come.

Now let's answer today's question. Why do the Yankees seem unable to rid themselves of the big, expensive mistake contracts they sign players to? The obvious answer seems to be that in the case of the Devers blockbuster, a still in his prime, highly productive player was offloaded to a team that coveted said player. I'm not sure any of the Yankees bad contracts can be compared to the Devers trade, as none of the players that come to mind are/were performing at a level high enough to motivate other teams to want the player.

Players with health issues and huge contracts (like Giancarlo Stanton), who also had full no trade clauses in their contracts mind you, became literally impossible to move. Cashman would love to trade Marcus Stroman too, but he's injured and he simply hasn't performed well enough on the mound to net a good return. DJ LeMahieu is another example of a player owed a fairly big sum, yet he hasn't been healthy for years now and is only just now swinging the bat at an okay clip. In other cases, Cashman hung onto a player too long, passing up a much larger return and he wound up eventually receiving next to nothing back - Joey Gallo comes to mind here. At the time Gallo was dealt, he was worth $$0.9 MTV when only four months prior, he was worth $15 MTV.

Also, trades have to ultimately match up. In the case of the Devers deal, the Red Sox took on a bad contract (Jordan Hicks) and received back a useful reliever, a top five prospect and a lower level prospect for an All-Star level player who the team wanted to unload, likely for reasons not related to his on field performance. Devers had worn out his welcome in Boston due to his unwillingness to play first base and the Red Sox simply didn't want to be on the hook for his contract any longer. 

Personally, I think Boston could have gotten a lot more for Devers had they waited until the Deadline to deal him. If I had to give Boston a trade grade here, the Sox would get an D to an F from me, and the Giants would receive an B+ only due to the money owed to Devers over the life of his contract. Let's fact it, Devers is an elite offensive talent - any way it's sliced. He is an exceptionally good hitter.  It's not possible to view this trade as being a win for the Red Sox as they basically lost an All Star for a bag of peanuts, a hot dog and a Miller Lite. 

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Editor's Note - The graphic was created by Google Gemini. The prompt used was: "Can you create an image of a baseball executive at a table with baseball cards of Yankees players and a stack of money also on the table as if he is making deals."