Yanks In Win Now Mode

Brian Cashman Is Betting It All On the 2024 Season With Off-season Transactions

By Derek McAdam

December 20, 2023

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The New York Yankees have already made a couple of big splashes in the trade market this off-season, acquiring Alex Verdugo from the Boston Red Sox and Juan Soto from the San Diego Padres for a total of eight players combined. Brian Cashman is still heavily involved in the mix for several free agents, including Yoshinobu Yamamoto, in his attempt to assemble a roster that can improve from the 82-80 Yankees from 2023.

But there is one crucial piece of information that has resulted from Cashman’s decisions: he is throwing all of his chips into the 2024 season and is not eyeing the long-term future. And there are several indications as to why he is possibly doing this.

For starters, this is a big season for the front office and coaching staff. Aaron Boone is entering the last season of his contract, although he does have a club option for 2025. While Cashman still has three seasons left under his deal, I don’t think he would keep his job if Boone is not able to keep his. It would obviously mean that the Yankees had another disappointing season, and with as much as Cashman has given up to bolster the roster, the team will be under the microscope.

Second, and perhaps the most important reason, is that the Yankees are slated to have several holes in their roster following the 2024 season. As of right now, three of their nine projected Opening Day position players will be free agents after the season: Verdugo, Soto and Gleyber Torres. Anthony Rizzo and Gerrit Cole also have options in their contracts, with the latter being a player option.

It is highly unlikely that we will see all five of these players playing elsewhere in 2025, but it is definitely a possibility that several of them find new teams. The Yankees know that Soto is going to test the free agency market after the 2024 season, but if Cole has another solid season, he will likely try and enter the market with Soto. However, the Yankees do have the option to add a fifth year to Cole’s contract if he does enter free agency, which would then lock him into a new five-year, $180 contract with the Yankees.

Do the Yankees want to take a gamble on five more years of Cole after 2024? I think it’s a dangerous move to make, but one that I can definitely see them making. He will be 34 in September and in most cases, pitchers don’t work out on long-term deals this late in their career. It may be a solid two seasons that they get out of him, but those last three will be long and hard to work through.

Plus, how much would it take to sign Soto or Verdugo or Torres to new deals? Chances are they wouldn’t re-sign all three of them, but Soto is the big name and he will command a lucrative deal. Torres is also in line for a nice payday, and while the Yankees may decide that their abundance of middle infield prospects could fill that hole, his bat will be missed at the plate, as he was arguably the best hitter on the Yankees in 2023.

It’s not as if the Yankees have assembled a potential dynasty with these recent acquisitions.

The third point is that Cashman is truly convinced that the Yankees are just one or two pieces away from contending in the playoffs. Bringing in Soto and Verdugo will likely improve the offense, especially since they are both good contact hitters. If Aaron Judge and Rizzo can both remain healthy, they can also be good hitters at the plate, in addition to Torres. But they’re also hoping that DJ LeMahieu can come back and have an improved season at the plate, similarly to Anthony Volpe. If (and it’s a big if) the Yankees can get solid production out of these few players, they can afford to have someone like Giancarlo Stanton in the lineup.

The team doesn’t have to have nine solid hitters in the starting lineup every game. Would it be nice? Absolutely. But it’s very challenging to assemble a roster that is capable of doing that. Even if the Yankees have five players who can have good averages, they will likely find themselves winning more games.

Cashman is also attempting to assemble a more healthy team. In his four seasons in Boston, Verdugo only missed a handful of games each season and Soto has been able to keep himself healthy (for the most part) for his entire MLB career. The Yankees have been working with Stanton in hopes that getting him slimmer will help with his overall health. The organization is also hoping that Rizzo and LeMahieu have fully recovered from their injuries and also hoping that playing Judge in center field will avoid any freak accident injuries occurring.

However, injuries are going to happen. It’s part of the game and every team has to encounter this. But the Yankees are hoping to avoid the injuries that last several weeks which lead to months.

Here’s the real issue with everything I just said. Everything looks good in hypothetical situations. Sure, if the Yankees are able to stay healthy and have a productive offense, they might be able to make a run in the playoffs. But that’s a big IF. We don’t know if Rizzo is fully healthy. And Yankee fans are very cautious about this because of the past troubles of Clint Frazier, who struggled with concussions. What if another player gets injured in some strange way on the field? The Yankees had two of them occur last season in Rizzo and Judge, so it definitely could happen again.

What’s certain is that Cashman is putting all of his eggs into the basket called the 2024 season. It’s a risky move that may pay off, but it’s one that we are a long ways away from finding out the results. The first, and most important, step is that the regular season games have to be played first.