End of Season Assessment

End of Season Assessment

…October Thoughts from Cary Greene

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I’ll lead with this: I'm really surprised the Rays made such short work of the Yankees, especially given how NY played vs the Red Sox in the Wild Card round. Victor Mesa Jr, the Rays right fielder who has been tabbed by Kevin Cash as the player who will likely be the Rays center fielder in the future, summed it up best during his postgame interview by saying, "We just wanted it more." Let that sink in.

I came away from the contest with those words ringing in my ears. Why didn't the Yankees match or exceed Tampa's desire to win? The Yankees play sloppy baseball and against elite competition, they tend to crack, we know that much. NY's roster is composed of a bunch of fat cats on hefty contracts, then Cashman cobbles the rest of it together with AAAA talent, scrap heap pick-ups, and now thankfully, a few home grown players who miraculously weren’t traded for veteran players on expiring contracts. 

It's time for the Yankees to develop a new process. Full stop.

Cashman's process doesn't work. It just doesn't. It's been 17-years man! The Yankees are still routinely getting outclassed in the postseason by "the better team." So this year, how did the "better team" - the Rays, do it? The short answer is their Division Series roster was comprised of:

●      15 players they traded for

●      3 players they Drafted

●      4 free agents

●      2 MiB free agents

●      1 International Amateur signing

●      1 Rule 5 Draft pick up

Drilling into it, their Division Series roster was positionally built with one player who they acquired as an International Amateur (Johnathan Aranda) and two who they acquired with Draft picks (Chandler Simpson 2nd Round  & Taylor Walls, 3rd Round). The rest of their positional roster was built with trades (Yandy Diaz, Junior Caminero, Liam Hicks, Victor Mesa Jr, Johnny DeLuca, Richie Palacios, Nick Fortes, Ben Williamson and Ryan Vilade) and two reasonably priced free agents (Cedric Mullins and Jorge Mateo) rounded out the Ray’s bench.

Looking at the Rays Division Series pitching staff, they built it with six shrewd trades (Drew Rasmussen, Freddy Peralta, Bryan Baker, Tyler Wells, Garrett Cleavenger and Griffin Jax), one Draft pick (Ian Seymour, 2nd Round) one Rule 5 Draft pick  (Kevin Kelly), two terrific Minor League free agent signings (Cole Sulser, Cam Booser) and two free agents (Nick Martinez and Steven Matz).

Now let's contrast the Rays blueprint to that of the Yankees. The Yankees Division Series roster was comprised of:

●      10 players they traded for

●      9 players they Drafted

●      4 free agents

●      2 MiB free agents

●      0 International Amateur signing

●      1 Rule 5 Draft pick up

What can the Yankees learn by comparing their process to that of the Rays? Well, for one thing, the Rays are very good at trading players who are nearing the end of their arbitration eligibility and they win the vast majority of those trades by getting back controllable, Major League ready prospects who their advanced scouts feel will be very successful Big League players. Clearly, the Yankees very rarely make trades like this. When trading, the Yankees process is to take on established talent while giving up in return, the kinds of players the Rays target. This is the first thing I would point out to Brian Cashman to illustrate what is dramatically wrong with the Yankees process, which he feels is excellent. Folks. It isn’t. Again, full stop. Let that marinate.

Next, we can see that the Yankees have had zero success with International Amateur signings. Not that the Rays have knocked it out of the park here either. After studying the Rays entire system, I would rate their International Scouting Department about the same as that of the Yankees - not very good. Keep in mind, I’m putting the sad story of Wander Franco aside here.

Somehow, even though the Rays always seem to Draft much higher and much more often than the Yankees do, the Yankees clobbered the Rays in terms of the amount of home grown talent they transitioned to the MLB level. Do you find that surprising? I will admit that I did. The Yankees actually use the few picks they get in the Draft very well. This indicates that the Yankees Draft process is alive and well.

Both teams are comparable with regard to signing players that other teams DFA, though the Rays had far more success in this department as illustrated by the cas of Cam Booser. They saw something in him that the Twins certainly didn’t.

Despite the enormous difference in the two team’s payrolls, $310 million for the Yankees compared to $90 million for the Rays, the Rays were the superior team in the Division Series. Granted, it's a small sample size, but they were also the superior team during the regular season, so let's not candy coat this. Tampa spent less than ⅓ of what the Yankees spent, and they put a superior product on the field this year.

In terms of spending on free agents, the Yankees, despite all their resources, had only 5 free agents on their ALDS roster. Again, full stop. Another massive problem with the Yankees process has shown itself thanks to this comparison. The Yankees allocated $160.8 million this season to Aaron Judge (non-factor, out injured), Giancarlo Stanton (ditto), Carlos Rodon (didn’t even use him), Max Fried and Cody Bellinger. That’s more money than 13 MLB spent this season. Coincidentally, only four of them made the playoffs (Rays, Guardians, Brewers and White Sox).

Is Brian Cashman getting postseason bang for the buck out of his free agents? Clearly, he is not. He also isn’t getting very much help from the players he’s been trading for - aside from David Bednar, none of the moves Cashman is making are really working. I’m going to be brutally honest here. I’m evaluating Brian Cashman’s real performance here and it’s not good folk. Here I go again, but it needs to be done, full stop.

Not to worry, I’m just getting started here and the goal is pretty straight forward. I’m going to give it to you like it is.

If you’re a Yankees fan, you may not like or agree with my season ending assessment, but one thing I hope we can concur on is that the Yankees play sloppy baseball against good teams in the postseason, they don’t hit consistently in the postseason and therefore, they can’t score when it matters most and lastly, the Yankees are a poorly run franchise that just got embarrassed by one of MLB’s lightest spending teams.

Onwards and upwards we go, because there is reason to have some hope for the future if you’re a Yankees fan and we’ll get to that soon.

But first, I've had the feeling all year that we're just watching the inevitable unfold - the Dodgers will win another Championship in all likelihood. It’s like that movie you hate that is constantly replayed on HBO. We don’t have to watch it again this postseason, do we?

I don't see any possible way that this year’s Yankees could have taken out LA head to head, so it's just as well that the Rays eliminated them. Maybe the Rays can beat what some in the media say is a vulnerable Dodgers team. I’ve read here and there that “the Dodgers can be had.” Oh really? Well, I’d love to see that happen, I truly would. I will tell you one thing for certain. I won’t be betting against LA this postseason, but alas, I’d love to see them take one for the sport. Enough already! Can somebody please beat them?

This is neither here nor there, but I sold my Aaron Judge jersey last week on eBay for $1. I had only worn it once. It seems like every Yankees fan has one. During Game 3 of the Divisional Series, fans all over the stadium were wearing number 99 jerseys. I’ve never been one who wants to be like everyone else, Judge’s jersey isn’t for me. In fact, I need a break from seeing his face in the dugout. I know, I know, he’s a modern day Babe Ruth, a generational talent..etc. Well, Babe Ruth won seven championships (four with the Yankees), so Judge is not really a modern day Ruth, but he is a can’t miss, first ballot Hall of Famer and he is a great player when he’s healthy.

Ruth also missed chunks of time (50 to 60 games) due to injuries and illnesses here and there during his 22-year playing career. Injuries are indeed part of the game and I’m not disputing that. Meanwhile, Aaron Judge has played half as many years to date as Ruth did, yet Judge has missed almost 300 games due to injuries. You see, Ruth was infinitely more durable than Judge is. Durability is a very underrated part of what makes great players into champions.

Case in point, Lou Gehrig won 6 championships with the Yankees. Gehrig slashed .361/.477/.731/1.208 OPS in the postseason. Ruth slashed .326/.467/.744/1.211 OPS in the postseason

We just witnessed the heart of the Yankees lineup, #3-#4-#5-#6 (Garcia, Goldschmidt, Bellinger, Lombard, Wells, Stanton, Jones and Chisholm) go a combined 3 for 42 (.071 AVG) against the Rays. Talk about letting down your excellent pitching staff. Wow!

Maybe the Yankees don’t win all those championships in their heyday if their two best players are unavailable when it matters most? Just sayin.

Aaron Judge has never won a World Series. He may never do it. That would be a shame.

In a postseason war of attrition, the Dodgers will likely grind their opponents down. Skubal, Snell, Yokamoto, Glassnow, Ohtani, Sassaki, Freeman, Diaz, Scott...on and on. Can the Rays somehow take them down?

I said it last offseason, more than once (in case any Yankees execs are reading this - LOL) -the Yankees needed at least one more  highly productive bat to take over for when, not if, Stanton got his next series of injuries. Hal Steinbrenner didn't want to spend to give the Yankees the right pieces and all he did was run it back. Instead of reinforcing the heart of the Yankees lineup, he chose to stand pat. He doesn't deserve to win a championship, he really doesn't.

Instead of scooping up Randy Arozarena, who made a ton of sense, the Yankees chose to extend the QO to Grisham, which ultimately blocked the path to making a run at Arozarena. Grisham was a below average MLB player this season, both offensively and defensively. The Yankees put their faith in StatCast, who said what Grisham did in 2025 was no fluke. At the time, I didn’t hate them doing this, but had I known that would preclude the Yankees from adding more pop to their lineup, I would have firmly been against it.

You see, we average fans don’t really know how much Hal Steinbrenner is going to spend each offseason - but Brian Cashman clearly does, so extending the QO to the guy who struck out to end the Yankees season turned into a pretty hefty mistake.

Unfortunately, for Grisham’s part, while he was very unlucky at the plate this season, he battled hamstring injuries this season and he just never got on track. Steinbrenner also failed to make other moves.

Mike King was there for the taking this past offseason. There were several relievers available as well, but all of these moves would have cost pretty big bags of money. Not to mention, Steinbrenner let Cashman go into the season with Ryan McMahon as his starting third baseman and Jose Caballero as his starting shortstop. Again, full stop.

No Kazuma Okamoto to buttress third base for the foreseeable future. No Pete Alonso or Kyle Schwarber to plug in at DH to replace Stanton - who let’s be real, should have been DFA’d this past offseason. Imagine a Yankees lineup with Okamoto, Arozarena, and Alonso in the heart of it? The Yankees generate enough revenue for this vision? Why didn’t it happen? One last time, full stop.

The New York Yankees brinks truck should have backed up in all of these players driveways this past Christmas, but it never happened.

While the Yankees got very good pitching this season, they lagged badly on offense. They wound up being a slightly below average team on offense. Eight of this year’s 12 postseason teams had vastly better offenses than the Yankees did. This is unacceptable. Clearly, the planning just wasn’t good on the positional side of the ball. Ultimately, the Yankees were a 93-win team this season. The same ol' "Good Enough" concept. This has been going on in the Bronx way too long. It was Benjamin Franklin who said, “Beware of too little expenses, a small leak can sink a great ship.” First and foremost, Hal Steinbrenner runs the Yankees to provide a profit. He’s only ever spent 48% (max) of the Yankees profits on payroll. This is not a commensurate spend compared to many other playoff teams. Hal believes spending excessively just isn’t fiscally responsible. He’s never been a team owner who is all-in on winning the World Series.

All Yankees fans know this, because Hal has taught us to know this over the years. He’s not a guy who will swing for the fences and go for broke. He does spend though, but only up to a point. He’s not willing to part with his profits in order to put the Yankees over the top because that’s not what owning the Yankees is about to him.

On that note, Steinbrenner, to his credit, sold a 16% stake in the team to Apollo Global Management this year, which will infuse the Yankees with $2.6 Billion that they can devote to operating expenses and purportedly - this rather large chunk of change may also go in part towards boosting the Yankees payroll in the coming years. Perhaps this will go down as the best thing Hal Steinbrenner ever did? Time will tell, there’s no guarantee that spending more money will win that elusive 28th World Series title that Yankees fans want so badly, but an extra $2.6 Billion can’t hurt, right?

Perhaps Hal realized he needed to find a solution to counter his critics and appease a fan base that has grown to despise the way he allows the team to be run. Or, maybe Hal just found a solution to help the Yankees try to win a championship. None of us can say the Yankees haven’t been competitive during the 17-year championship drought, heck, they’ve made the playoffs 13 times since 2010. Most franchises would be very happy with that, but therein lies the problem. The Yankees are not most teams, so they require exceptional leadership that wants to win with an unrivaled sense of urgency. There’s that concept that Victor Mesa Jr summed up by saying, “We just wanted it more.”

Imagine what would be possible if, from the top of the Yankees organization on down, a true desire to become champions cascaded throughout the organization and lit a fire in the hearts and minds of the players. Can you envision 26 players, the manager, the coaches, the GM and even the owner going all out in order to win it all?

Let’s be real for a moment, we can’t say that about the Yankees right now.

Yankees fans have grown very accustomed to their team not really being involved with many of the top free agents, hopefully the deal with Apollo will change that narrative in the years to come, but it’s pretty obvious that the Rays just proved that the Yankees process that unfolds due to Hal Steinbrenner’s fiscal responsibility isn’t working. Would more spending and better preseason planning fix a lot of the Yankees problems? It might. It might not. There are no guarantees in baseball.

I’m skeptical because it doesn’t really feel, from the top of the organization down, that the Yankees really do want to win it all. I don’t see how Apollo getting involved would be able to impact this key piece of the Yankees real problem. It starts with Hal Steinbrenner. He’s reclusive. He doesn’t want the media spotlight. He wants his leadership team to get the job done, all they need to do though, is be good enough. He’s obviously satisfied with that.

I’m going to conclude this end of the season assessment with these simple recommendations.

1.     If there is a 2027 season, the Yankees need to spend positionally on the right free agents and they also need to reinforce the pitching.

2.    Aaron Boone needs to go.

3.    Brian Cashman needs to go.

4.    Michael Fishman needs to go.

5.    Somebody who wants to win needs to be brought in as the GM. Derek Jeter is my pick. There are others out there.