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Tuesday Discussion: Is it Time? (Part II)

by SSTN Admin

May 16, 2023


This week we asked our writers:

If you were the owner of the Yankees, at what point would Brian Cashman's job be in jeopardy, if at all, in 2023?

Here are their replies:


Cary Greene - If I were the owner of the Yankees, Cashman would have been promoted to team President long ago, so for me the question for this week is kind of moot. Cashman's prior results, combined with his real skill set, would have dictated his fate. I also don't believe that the "process" that the Yankees use is necessarily as good as Cashman routinely portrays it to be.

My main reason for promoting Cashman is that I think he's more of a front office guy than he is an actual baseball decision maker. He's also demonstrated that his heart is in the right place. He's loyal and grounded, he gives to charity and I think he's an organizational lifer. How much he's invested himself in the organization kind of get swept under the carpet. He's worked without a contract in the past and he's also pretty relentless and tireless. He knows baseball, and he does a pretty good job mining baseball's scrap heap every off season.

Cashman could also probably help and support a real baseball GM type and that could be beneficial to the team's overall success.

My reason for wanting a better baseball person to run the organization is probably rooted in my disapproval of the Yankees talent evaluation results and also my preference would be steeped in reverse engineering. My goal is an old school one, for I believe the Yankees organizational goal should be to win a championship each season, not simply to be good enough to make the playoffs. Perhaps that's where I would differ in that regard from current team owner Hal Steinbrenner.

What I'm saying is that therefore, if I was the team owner, I would hold myself responsible first and foremost. If the Yankees failed to win a championship, I would have to look myself in the mirror and ask myself the difficult questions, like where did I go wrong or what could I have done differently. Spending is part of this equation but there's more to it than that.

To Hal's credit, he's spent quite a bit of money on the team. He has the second highest payroll in baseball. But what did he get for the spend? More importantly, If the Yankees fail to win a championship this year, they will tie the all-time Yankees worst mark for futility, 14 years and running with no ticker tape parade. As the Owner of the Yankees, the brand would be more important than anything to me and the brand has been built on championships. It hasn't been built on being good enough to make the playoffs. Championships are what the Yankees are built on. With the second highest payroll in baseball, doubling down on my investments in players like Gerrit Cole and Aaron Judge would be viewed as an organizational necessity. Surrounding them with necessary players while also insisting certain players were kept and not traded or given away would all be part of the puzzle. Granted, my payroll for this season would probably the highest in baseball, but I don't think it makes much sense to load up on just a few star players when clearly there was so much more to be done. That begs the questions - Why are there so many ragtag players on the Yankees, why is the lineup so unbalanced, why doesn't the team have an established closer, why is it taken so many years to build a rotation worthy of dominating in the playoffs and why do so many players in the Yankees farm system wind up succeeding for other teams instead of the Yankees? Since I don't believe Brian Cashman has plausible answers to any of these questions, I don't believe he's fit to be the team's GM. As the Yankees team owner, It would be my job to make the tough decision to bring in better baseball people to run the roster building piece of the puzzle. As much as I like and respect, Brian Cashman, I think he's very out of touch with the players in his own system, let alone those on the free agent market.


Paul Semendinger - Brian Cashman has done an excellent job for the Yankees. The Yankees are in the playoffs almost every year. They have had a winning record for the last three decades. The last time the Yankees failed to have a winning season was 1992. Holy cow! That's a long time ago. There is a lot that has gone right.

But, we have also been told, and sold, on this idea that the Yankees' mission is to win World Series.

Brian Cashman has been a great GM at building teams that are better than .500 (often much better) and that reach, but fail, in the playoffs. That's his legacy. Overall, compared to every other franchise, that's great. For the Yankees, it's not good enough.

Now, I feel one reason the Yankees haven't been able to make the next step forward is that, in spite of the spending, the Yankees do not ever go "all-in." Every year there are very clear weaknesses on the team - weaknesses that could be addressed, and should be addressed and aren't. It seems the Yankees spend with out a long term plan in place, but when they reach a certain point, they stop spending regardless of whether the team's needs have been met or not. They spend, spend, spend... and then they stop.

If the team operates under a hard cap, investing $20+ million on a player past his prime like Josh Donaldson makes no sense. Does the blame for this fall on the owner or the GM? Or both?

Last year, Brian Cashman's deadline pitching deals all turned out poorly. Every one. That's tough to recover from. Brian Cashman has been acquiring lots of players that cannot stay healthy. That's also a problem. When players who are frequently injured get injured again, that's not bad luck, that's bad planning.

Brian Cashman has been a very good GM. He belongs in Monument Park. He even belongs in the Baseball Hall of Fame. Yes, he's been that good. But, all people, in all jobs get to the point where they are not as effective as they used to be. Great CEOs move on. Great Presidents of the United States leave office. On and on. In every industry there comes a time when leadership changes. Organizations need vibrancy and new approaches. If the goal is a World Series, it is clear that the current approach that the Yankees are following isn't working. Since 2004, the Yankees have been to just one World Series. That's a long time. That's a lot of years where the Yankees fell short of their goal. (And if the goal isn't to win the World Series every year, that's a bigger problem.)

If I were the owner, knowing I just gave Brian Cashman an extension, I'd take the spending limits off and say, "I believe in you, build me a winner." I'd allow Cashman an unlimited budget to do whatever is necessary. I'd also make that known. "I am giving my GM whatever resources he needs to build us a winner within three years." It will be clear after that time if Brian Cashman is the reason the Yankees can't reach the World Series or if it's the owner's spending restrictions.

I believe Brian Cashman is smart enough not to fill the roster with dozens of $40 million players. I think he'd still find excellent players, as he has done. But I also believe that had he been allowed to spend more freely, the Yankees might have more than one lefty in the bullpen and more than one lefty bat in the line-up. I also believe he would have better addressed left field. I think, if he was permitted to use his baseball smarts, that Brian Cashman would build a winner. I'd love to see that.


Ethan Semendinger - I've wanted to write a post about this after hearing a quick bit about Brian Cashman from "The Michael Kay Show" sometime this past winter, but never got around to it. Ultimately, I could never find the right words to explain Cashman's security within the team. Fundamentally, however, it appears as though Brian Cashman is the "5th Steinbrenner". After Hank, Jessica, Jennifer, and Hal, there has been a de facto adoption of Brian Cashman that stems back all the way to 1986. He will never be fired. He has gotten too close to the family to ever be on the chopping block.

It's a moot point to argue at this point with Cashman, especially after he was just granted another 4 years (through 2026) to run the club as the General Manager. At this point, the decision is entirely in Cashman's hands about when he wants to leave his job. And, when that happens I believe he will be transitioned into a background position as the President or COO.

Or, maybe that's the key. Maybe when Randy Levine (the current president) or Lonn Trost (the current COO) leave their positions, then Cashman will move up the ladder and there will be an opening for the Yankees. They're far too loyal to their employees.


Tamar Chalker - Cashman has been on thing ice with me for a while now. The injuries that continue to plague the Yankees (particularly early in the season) has become too common to consistently be a fluke. Unless the Yankees really bounce back and have a solid playoff run this year, I’d be looking for a new GM in the offseason.


Mike Whiteman - For me to consider Cashman’s job to be in jeopardy, I would need to see a total collapse in the team. The team would need to fall significantly far out of playoff contention, and be sellers at the deadline. At that point, it may be time to “kick him upstairs”, and bring in another GM.

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