Perspectives: Would YOU Sign With the Yankees?

by Paul Semendinger

October 23, 2023

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I made this point in the comments of an article about Jordan Montgomery the other day. I then decided it needed its own article:

I have a fair question to every Yankees fan...

If all things were equal, would you play for the Yankees over a club like the Dodgers, Braves, Phillies, Rays, Orioles, Rangers, Astros, etc...

I love the Yankees. My dream has always been to play for them. I write about them every single day. BUT, if I were a Major League Baseball player, and any of those other teams offered me a similar contract, I'd go to those teams. Absolutely. 100%. This isn't because I don't like the Yankees. I love them. But as a professional, it would also be clear that my career would have a better chance of thriving with a better run organization. That's just the way it is.

I do not think the Yankees, as a franchise, outside of the fact that they won a ton of World Series, many years ago, and have history on their side, are a prime destination for many players. Sure, they'd love the allure of pinstripes. Sure, they'd love being part of Yankees history, but, in a real sense, what do the Yankees of today have to offer players?

Many players come to the Yankees and fail.

Most Yankees prospects fail to produce or find any success in the big leagues.

Many players leave the Yankees and perform (much) better.

These are facts. These facts are undisputable.

Also, if one looks through the weeds, I don't think their management team is well-thought of in the game. I'll ask a simple question...

Why is it that most teams (if we are to believe the Yankees) always seem to ask for more players in a deal from the Yankees than any other team? Is it possible that it is because they'd rather not deal with the Yankees' front office? Isn't that a possibility? I think this is more of a possibility than the idea that other GMs don't want to be burned by Brian Cashman. How many current GMs has he even burned? Yet, that is the excuse we often hear. The fact of the matter over the last few years is that much of the time, it's the Yankees that get burned. Just looking at this from a distance - If it seems it is difficult to deal with a team, maybe the problem is the leaders of that team, rather than the other guys (although, again, most often we are told it's the other way around).

Also, again, if one digs deep enough under the surface, he can find examples of Yankees icons like Bernie Williams, Derek Jeter, and even Aaron Judge critiquing the way that their negotiations were handed by Brian Cashman. We see stories that follow a similar pattern, "I felt disrespected after all the years I gave the club," and "We asked one thing, for the negotiations to be kept private... and then we saw the reports in the media. We didn't share that stuff... it was the Yankees." It seems that all too often the greatest Yankees' tenures with the team ends, not in glory, but in strife. The other players around the league, their agents, and etc., have to know this.

Would you go to a ball club that disrespects you in the end? I don't think I would.

There was a time when players would desire playing for the Yankees because they felt that the Yankees would do everything in their power to win. That is clearly no longer the case. Other teams are bigger winners. The Yankees have won one World Series since 2001. That's a long time. Since the All-Star break in 2022, a year-and-a-half now, the Yankees are basically a .500 team.

Are the Yankees ascending or, even after a long long period with no championships, still on the downturn?

It is my contention that there are a host of clubs that are better run than the Yankees.

What are the selling points to play for the Yankees in 2024 if all other things (years, contract value) are equal?

Is the Yankees' scouting better?

Is their player development better?

Is their decision making better?

Does their medical staff properly treat injuries and recovering players?

Do you feel they have a top notch coaching staff with the MLB team?

Do they invest more in winning?

Is their manager seen as one of the best?

Is their stadium one of the best places to play?

I'm serious about this.

What is there to make a player say, "The Yankees are the place to go that'll further my career, my skills, and give me the best chance to win?"

I am very interested in our readers' reactions to this question. If you were a big league star and the Yankees offered you the same contract as any of the top teams in the game today, would you sign with the Yankees or another club?

If you'd sign with the Yankees, please explain why. If it's the fact that you've always been a fan or that the Yankees used to be winners, I'm afraid that those reasons won't guide players today.

I'd like to know, what is it about the Yankees today that makes them an appealing destination for the game's biggest stars - or really for any available free agent?

I think the answer to this question is telling and it is a clear indication that something is terribly wrong with the Yankees today.

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