top of page
  • Derek McAdam

The Upcoming Yankees’ Off-Season...

The Upcoming Yankees’ Off-Season May Be the Most Challenging Winter Ever For Cashman

By Derek McAdam

October 4, 2023


It’s now been several days since the New York Yankees finished their disappointing season in many years with an 82-80 record. At some points in the season, especially in July and August, it didn’t seem as if the Yankees were going to continue their 30-year streak of having a winning record, although their strong run in late August into September helped them achieve that goal, which doesn’t carry much weight today.

The Yankees’ front office, coaching staff and players will now look forward to an off-season that is going to be full of decisions to be made, most of which may not even involve player transactions. Many of these moves, none of which will probably involve the firing of Brian Cashman and/or Aaron Boone, will be behind-the-scenes changes, which may include evaluations of the training staff as well as a re-tooling of the analytics department.

But this is where things may start to get tricky for the Yankees, for several reasons. First, and foremost, Cashman has put the team in a situation to where very few Yankees have any decent trade value. Gleyber Torres is one of the few expendable Yankees that is not a first- or second-year player and doesn’t have a large contract to his name. While it is a possibility Torres could get traded, he may be one of the few players that the Yankees could actually get a decent return for. Anthony Rizzo is another player that has some value, but I can’t see the Yankees trading him.

Cashman has also put the team in a bind with so many large contracts. Aaron Judge, Gerrit Cole and Giancarlo Stanton all have contracts north of $300 million (even though Stanton did not sign his with the Yankees, I’ll still include it for reference). Carlos Rodon and DJ LeMahieu both have several years left on their deals as well, with Rodon still with a half-decade to go. Of all these players, Judge and Cole are the only two that had good seasons. Judge, although he was hurt for two months, still had a productive season. While LeMahieu did have a much better second-half, the first-half really strained his season.

Of these five players, Judge and Cole are likely the only two players that another team could possibly be interested in acquiring, but that doesn’t even mean that there are. This puts the team in a tight spot with regards to free agency. While it’s known that the Yankees have interest in signing Japanese pitcher Yoshinobu Yamamoto, this may not become a reality for two reasons. The Yankees may decide to invest whatever money they are willing to spend in a position player(s) or may face the reality of being out-bid by another team for his services.

However, one player is not going to make a difference on this team. Hal Steinbrenner seems to have hinted that the Yankees are not going to just get the analytics team to focus on other aspects of the game, but instead bring on a whole new analytical team. While this is definitely a step in the right direction, this is a problem that will likely take years to sort out, especially for the younger players.

It’s hard to imagine that someone like Stanton will make the adjustments to the new stance in analytics, considering how his past two seasons have gone. I’m not saying it’s impossible, but it is going to take a lot of work from Stanton to make happen. But so many of these Yankees players are simply not great hitters because of what they were taught in the minor leagues, which is the approach to hitting the ball hard and with a specific launch angle. How many times this season did we see Anthony Volpe swing and miss with that uppercut swing, which is tailor-made to satisfy the analytics department’s love of launch angles? Too many to count.

But there’s not only questions regarding the offense, but what about the pitching staff? Cole had an excellent season for the Yankees, but what about everyone else? Who is the No. 2 starter on the team going into next year: Michael King, Nestor Cortes, Clarke Schmidt, Rodon or someone else? There are so many questions up in the air with the rotation that it is simply too early to call. Not only that, but can Cortes come back and return to his form from a couple of years ago, while also being able to stay healthy? Is King actually continue to give the Yankees quality starts next year? Can Rodon return to his old form? All of these questions are on the table this off-season.

Steinbrenner seems to be much more vocal about the ongoing issues that the Yankees will need to address this off-season, although he has not yet addressed the biggest problem of them all: Cashman. The Yankees are currently in this spot because of all the moves that Cashman has made. He has hired a coaching staff that is told to live by the analytics and has signed players to ridiculously large contracts that the team will be stuck with for years, nearly all of whom have underperformed.

Yes, Boone has made plenty of bad decisions over the course of his six seasons in charge of the team, and despise his philosophy of holding starters to lower pitch counts early in the season that ends up putting extra stress on the bullpen later in the season, but he did not assemble this team, the coaching staff or the analytics department. He had to work with that team that was given to him, and there’s only so much he can do for a team that simply can’t hit.

What the Yankees cannot enter the off-season doing is deciding to add more large contracts to the team. At this point, the Yankees are not one or two or even three players away from making a run in the playoffs. They’re still a good distance away from competing, and it is going to take a lot of work to make happen, especially internally with the players they have now. It will be hard to teach some of these younger players who have spent years learning one method to completely drop it and focus on another aspect. This is all assuming that the Yankees decide to fix that issue.

For hypothetical purposes, let’s say that Judge and Rizzo would have both had much better seasons if it wasn’t for their injuries, which would have likely been true. There are still seven players that would need to improve as well, so having those two players playing very good definitely helps, but it wouldn’t define the team’s success. The reality of the game is that injuries will occur, even if both of the root causes of their injuries were freak accidents. The rest of the team then has to step up, which is what did not occur in 2023.

It’s going to be a very complicated off-season for the Yankees. The decisions on who to sign, trade or release are not going to be simple. Do they believe that this team is capable of making a playoff run and that re-tooling their approach to hitting will do it? Or do they think that making the ultimate decision to sign a big name in free agency is the way to go? If the Yankees have a poor 2024 season, it is likely that Cashman and Boone will both get fired, so Cashman may already be feeling some pressure that have a productive off-season, even if it doesn’t mean signing a player to a big contract.

Last off-season, it was pretty obvious that the Yankees needed to add a big name to the team, especially in the rotation. They did just that, but it turned out to be a disastrous first season in the Bronx for Rodon. Are they willing to jump right back in and go for another big name, or did Rodon’s failures scare them away from that tactic? Time will tell, but this may end up being one of the toughest off-seasons for Cashman since he became the GM.


Oct 04, 2023

At this point, the Yankees are not one or two or even three players away from making a run in the playoffs.

that's might be possibly correct. might not be if you consider that the return/ or return to form/ or maturation f some of the pitches should provide the team with a superior rotation and bullpen.

they have a good bunch of pitchers and an interesting pitching coach. Blake knows how to get results and gets them.....for as long as his guys are healthy.

the Yankee problems revolve around the offense.

and the offense features one superlative hitter

three seasoned (aging) supporting guys

and a bunch of kids.

it seems likely that at least one of Rizzo, DJLM and…


Alan B.
Alan B.
Oct 04, 2023

I really see it very simply, and these are my thoughts:

Cashman. He has to actually defend/prove it himself for any move he wants to make. Him, not a flunky, an assistant, etc. No more moves made simply because he's the head of the Baseball Operations.

The entire analytics based methods/process has to be thrown away. Back to more old school methods leading the way with analytics playing a supporting role.

Boone needs his own coaching staff. Does anyone really think Boone thinks Blake is a good game Pitching Coach? Or that Luis Rojas is a solid 3B Coach? Or that he would've kept Casey Dykes after Dillon Lawson was fired, and let's not forget, Brad Wilkenson was already …

dr sem.png

Start Spreading the News is the place for some of the very best analysis and insight focusing primarily on the New York Yankees.

(Please note that we are not affiliated with the Yankees and that the news, perspectives, and ideas are entirely our own.)


Have a question for the Weekly Mailbag?

Click below or e-mail:

SSTN is proudly affiliated with Wilson Sporting Goods! Check out our press release here, and support us by using the affiliate links below:

Scattering the Ashes.jpeg

"Scattering The Ashes has all the feels. Paul Russell Semendinger's debut novel taps into every emotion. You'll laugh. You'll cry. You'll reexamine those relationships that give your life meaning." — Don Burke, writer at The New York Post

The Least Among Them.png

"This charming and meticulously researched book will remind you of baseball’s power to change and enrich lives far beyond the diamond."

—Jonathan Eig, New York Times best-selling author of Luckiest Man, Opening Day, and Ali: A Life

From Compton to the Bronx.jpg

"A young man from Compton rises to the highest levels of baseball greatness.

Considered one of the classiest baseball players ever, this is Roy White's story, but it's also the story of a unique period in baseball history when the Yankees fell from grace and regained glory and the country dealt with societal changes in many ways."


We are excited to announce our new sponsorship with FOCO for all officially licensed goods!

FOCO Featured:
carlos rodon bobblehead foco.jpg
bottom of page