top of page
  • Writer's pictureSSTN Admin

Why Didn’t They Win?

By Cary Greene

December 1, 2021


While sitting around the fireplace drinking Apple Cider, munching on Snyder’s Cheddar Pretzel bits and eating amazing Turkey sandwiches made from Thanksgiving dinner leftovers, I began to wonder. It all started with the first bite of the sandwich. Turkey, Stuffing, Cranberry Sauce, Cheese, Bread (I call it a “Thanksgiving,” creative right? Maybe not the name, but the ingredients?) I wondered…,”Why didn’t the Yankees win a championship this year?”

They had all the makings, right? Hal Steinbrenner and Brian Cashman both said the team was capable of winning it all, didn’t they? I started wondering, “What went wrong?”

After all, pitching wins championships right? The Yankees started the season with high hopes in this department, but to be fair, numerous question marks were intertwined with those hopes. Corey Kluber and Jameson Taillon were both brought in. Clarke Schmidt and Deivi Garcia were both poised to burst into the rotation. Gerrit Cole was heading the whole deal up. There was a lot of excitement in the air.

Well, Things didn’t quite work out the way many of us hoped. Kluber started slow but came on to throw a no-hitter and then, poof. He was lost to an injury for most of the year. Taillon started slow but became at least serviceable. Nestor Cortes Jr stepped in and did a nice job this year. There were bright spots. There was also lots of inconsistency. Were the failures of Clarke Schmidt and Deivi Garcia really at the core of this year’s failure to win a World-Series?

I thought about how Schmidt went down with an injury and Garcia bottomed out like nobody’s business. Before the season, Garcia was quite the valuable commodity. Now, you couldn’t even get a player of equal value to Mike King for him in a trade. That’s how far Garcia’s value has plummeted. In fairness, the Yankees weren’t really counting on either pitcher. They might have absolutely been hoping one or the other, or both, would have breakout seasons – but they had a pretty solid game plan despite the question marks.

I realized something bigger held the Yankees back this season. It wasn’t Brian Cashman’s execution of his plan to get better necessarily, though we can debate that quite a bit. It was something more. During one stage of the season, the Yankees were getting dangerously close to being a .500 team. “The payroll is simply too-high to accept that kind of performance,” I thought.

I got to thinking about how badly Brian Cashman has fiscally mismanaged the Yankees over the course of several years. What prompted me to start thinking about this was of course daydreams about players I’d like to see traded and players I’d like to see acquired – which are fairly normal things for a die-hard Yankee fan to be thinking about in the offseason. I was focused on thinking about how the Yankees could get better, so they could not just contend, but win the World Series.

Certainly for this to happen, for the Yankees to win a World-Series, a number of trades and free agent acquisitions need to happen. “Why are the Yankees always struggling to stay under the Luxury Tax?” I thought. “Why is Cashman having such a hard time reshaping the roster?” I wondered.

Let me ask you as a reader an important question. Are you a Brain Cashman supporter? If you are, you might not be so much so after reading this article.

Did you want the Yankees to acquire José Berríos at the Trade Deadline this past season? I did and I also knew why Brian Cashman couldn’t make that happen. The reason was simple. Berrios was very expensive to trade for – meaning to do so would have required parting with a few of the system’s top prospects. Cashman did what he could at the deadline with what he had to work with, but there is a reason the Yankees decided not to trade for top players. Opposing teams want controllable, high performing players or can’t miss prospects in return. Trading teams need desirable players who make it worth it for the team giving up the difference maker. The Yankees are in very bad shape in this department.

Did you know that 23 percent of the Yankees current 40 man roster either has zero trade value or negative trade value? That’s almost a quarter of the Yankees roster that no team in baseball would give Brian Cashman anything for.

In fact, Cashman would either have to pay the other teams to take these players, or give up almost all of his top prospects to get these teams to take all this dead weight. “So what!” you say? “The Yankees can sign some of the best free agents!” you say? If this were true each season, wouldn’t Brian Cashman have already done that?

Did you know that the 23 percent of the Yankees 40 man roster that has no trade value or negative trade value is going to cost the Yankees more than $96 million in 2022 alone? That’s not even counting Tyler Wade, Rougned Odor or Clint Frazier, each of whom the Yankees recently basically fired. Think this might hurt the Yankees payroll wiggle room as they contemplate exceeding the luxury tax threshold(s)?

Making matters even worse, another 23% of the Yankees 40-man roster is chalked full of players who are even less tradable than Deivi Garcia. Come to find out, almost half of the Yankees 40 man roster has negative, none or marginal trade value.

I’m already skimming countless internet articles and posts that suggest the Yankees should trade certain players – most of whom have either miniscule trade value, no trade value or worse yet, tremendously negative trade value.

Personally I can easily think of four Yankees I’d love the team to be able to trade but unfortunately, it would be very difficult to trade each one of them. 1. Giancarlo Stanton; 2.Aaron Hicks, 3. Aroldis Chapman >> but each has significant negative trade value due to their contracts, the number of years remaining on said contracts and the relative cost of their performance.

We could also place DJ LeMahieu on this list, but the Yankees can live with a little negative value for now, given LeMahieu’s versatility and his defense. Granted, his defense is in decline, but the Yankees probably shouldn’t wish they could trade him just yet. Zack Britton could be on this list of players I’d love the Yankees to trade, but seeing as how he will miss all of next season and is under contract, no team would want him.

In order to trade any of these Yankees I’ve mentioned that I’d love to see traded, the Yankees would need to eat portions (or all of) their contracts or include highly valuable prospects just to get a team to take them. Their contracts are “that” burdensome.

Not counting these three pretty much untradeable players, the Yankees have another grim reality plaguing their 40 man roster and that’s the afore-mentioned number of players who have zero trade value, in other words, you could trade these players but you’d receive a player with no value in return. The list of zero trade value players includes 1. Albert Abreu; 2. Miguel Andujar 2. Wandy Peralta and 3. Gary Sanchez. Considering the overall value of each of these players and factoring in what they make, no one on this list would fetch a player with actual value.

The Yankees might believe some of these players are valuable, but no team would give up anything of value in return for this group of players. For example, personally, I think Abreu might be able to build some value with a solid 2022 season and I think he has the arm to do it. His learning curve has been steep, but he had a few impressive stretches of games and the Yankees didn’t exactly give him a chance to be consistent because they had him riding the Scranton Shuttle almost daily. Perhaps hanging on to him is better than moving him for nothing, if you get my logic.

“Who has value then?” I asked myself. “Which players do other teams actually want? I wondered.” Well, the point of this article isn’t just to expose the terrible fiscal management that Brian Cashman has accomplished to date. I’m not here to lament that the Yankees only have essentially about a dozen or so players that would make sense for them to trade and who could bring back something decent in return. I wrote this article so that fans could get a very accurate idea regarding which players are tradeable and how this list would be viewed by other teams.

My effort here should help everyone who cares to speculate do so realistically. Granted, Brain Cashman doesn’t have a lot to work with, but he could do some quality maneuvering and I believe he’ll absolutely have to get it right at this point, for the Yankees to have any chance of bringing home a World Series championship.

I’ll also go on record, here and now, to state that I don’t believe Cashman can come remotely close to doing what it would take to actually win a World Series. I am prepared to endure several more losing seasons until perhaps Steinbrenner up and sells the team. I don’t believe in what they’re doing and I don’t think they have the know-how to compete with other forward thinking organizations. I think Cashman’s plans are as flawed as his roster is fiscally mismanaged. You may absolutely disagree with me on this and if it makes you feel better to buy in or to hope, know that I don’t blame you in the least.

Below I’ve highlighted the trade value of the “Top-40 Most Tradable Yankees, System-Wide” irregardless of whether they are on the 40 man roster or not. I’ve also included the MLB Trade Value of each player on the 40-Man Roster as many of these players are there merely due to service time, not because they are particularly valuable. 40-Man Roster players appear in bold and minor leaguers without the needed service time appear in blue. Players with zero trade value appear in burgundy and players with negative value appear in red. I’ve also noted each player’s “Trade Value”as identified by MLBTRADEVALUES.COM for easy reference.

I’ve also taken this a step further. I’ve identified the players the Yankees might be willing to trade who could bring back a decent return. I understand that no player is truly untouchable so I made the list more to identify players other teams would value and then I looked for players who would be on the table if the return was deemed worth it.

Anthony Volpe (Trenton) 46.4

Aaron Judge 40.9

Johnathan Loasiga 27.6

Oswald Peraza (Scranton) 25.5

Jasson Dominguez 25

Jordan Montomery 24.6

Gerrit Cole 19.8

Joey Gallo 15.3

Luis Gil 13.1

Domingo German 11.6

Luis Severino 11.4

Gleyber Torres 10.8

Alexander Vargas (Rookie League) 9.8

Austin Wells (Tampa) 9.3

Nestor Cortes Jr. 8.8

Jameson Taillon 8.4

Luis Medina (Trenton) 7.4

Everson Pereira (Tampa) 7.4

Trey Sweeney (Tampa) 7.4

Yoendrys Gomez (Tampa) 6.8

Clarke Schmidt (Scranton) 6.8

Antonio Gomez (Rookie League)) 6.5

Chad Green 5.3

Ken Waldichuck (Tampa) 5.2

Kyle Higashioka 4

Hayden Wesneski (Scranton) 3.7

Mike King 3.4

Luke Voit 3.1

Deivi Garcia (Scranton) 2.6

Brock Selvidge (Rookie League) 2.6

Fidel Montero (Rookie League) 2.5

Gio Urshela 2.2

Clay Holmes 1.9

TJ Sikema 1.9

Estevan Florial 1.8

Ryder Green (Rookie League) 1.8

Hans Montero (Rookie League) 1.7

Marcos Cabrera (Rookie League) 1.6

Oswaldo Cabrera 1.6

Josh Breaux (Tampa) 1.5

Stephen Ridings 1.4

JP Sears .9

Joely Rodriguez .7

Chris Gittens .5

Lucas Luetge .4

Tyler Wade .3

Clint Frazier 0

Rougned Odor 0

Albert Abreu 0

Gary Sanchez 0

Wandy Peralta 0

Miguel Anduar 0

Aroldis Chapman -5.3

Zack Britton -15

Aaron Hicks -24.2

DJ LeMahieu -24.2

Giancarlo Stanton -111.1

Again: 23 percent of the current 40-Man roster has either zero trade value or worse yet, negative trade value. This would be an example of Brian Cashman’s poor decision making. This group of players who have no value or negative value aren’t remotely worth the money the Yankees are paying them. They will cost the Yankees more than $96 million for the 2022 season.


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