10 Reasons Why The Cashman Era Must End *NOW*

Brian Cashman. Took over as GM in 1998, after serving as assistant GM from 1995 to 1997. He oftentimes gets credited as the architect of 4 World Series titles with the Yankees, and in truth has only been the engineer for one title, inheriting a mostly ready to go team that Gene Michael built in the mid 90’s.

Having said that, after building only a single title team in 25 years, it’s time for the Brian Cashman era to come to an end. Here’s why:

1) Baby Bomber Bust

To grade a GM, you need to look over 5 years – 2 years to rip down the bad team while rebuilding the farm, 1 year of trial, and the final 2 years for the GM’s new team to do damage.

In 2016, Cashman had his ultimate moment when he finally convinced Hal Steinbrenner to rebuild. Trading away Chapman Miller and Beltran. Yankees fans sick of old, boring, injury prone veterans were flooded with optimism and embraced the new young core.

2017 was a magical year, and the Yankees made it all the way to game 7 of the ALCS with the likes of Brett Gardner, Chase Headley, Didi Gregorius, Starlin Castro and Jacoby Ellsbury (lol).


Brian Cashman and the New York Yankees put MLB on notice. We are good. We have young players all over the place. Aaron Judge. Greg Bird. Gray Sanchez. Clint Frazier. Gleyber Torres. Luis Severino. Miguel Andujar. Justus Sheffield. Chad Green.

Skip ahead 5 years to today. Judge is the only player worth mentioning and he may be out the door in free agency. Aside from Torres, every other player has disappeared. The Yankees only won the division two times, and didn’t get any closer to the World Series.

Heck, they went backwards since 2017.

And here’s the truly embarrassing part… After the 2017 rebuild year, the Yankees were eliminated two times by the 100-year rival Boston Red Sox., then division rival Tampa Rays with their non-existent payroll, and beaten another two times by the hated Houston Astros.

How many times can you embarrass your fans by losing to teams they absolutely loath and keep your job? Baby bomber era is over and will be quickly forgotten.

Fire Cashman

2) Cashman Can’t Win in October

First thing you think of when you hear “New York Yankees” is greatness, excellence, championships. 27 of them. THAT is the Yankee brand.

2004 was the worst moment in American sports history. The team that couldn’t win in forever came back against the team that always won. And both teams hated each other from the players down to the fans. For 100 years.

Everybody in the Yankees organization needed to be put on notice the second Johnny Damon hit the grand slam off Javy Vazquez.

It’s 19 years later and the Yankees have since made the World Series just one time. One. Damn. Time. 19 years and only 1 pennant matches the worst 19 year stretch (1903-1921) in Yankees history.


Cashman likes to call the playoffs a crapshoot. Is it though?

Since 2004 American League teams Rays, Rangers, Tigers and Royals have made it to The Series two times each. Premier teams like the Red Sox, Giants, Cardinals, Dodgers and Astros have each made it 3+ times.

Since that dreadful day in 2004 the Red Sox have won the world series 4 times with 3 different GMs. Dave Dombrowski is considered a mediocre GM. He’s beaten Cashman FOUR TIMES in October. The Astros have found a way to beat Cashman’s creations 3 times (+ a wild card).

The Yankees are 8-11 in playoffs series (Not counting fake wild card). Seems like the only teams the Yankees can “out crapshoot” are the poverty Twins and Cleveland team. 5 of 8 playoff series wins have come against those teams. Yankees are 3-11 vs teams not Cleveland or Minnesota.

Brian Cashman is singlehandedly ruining the Yankees brand of Championships.

And for that reason, Fire Cashman

3) Cashman Regular Season Issues

Getting back to Cashman saying the playoffs are a crapshoot. The goal of the regular season is to win the division. Five teams in a division, be the best, and you go straight to the division series and can avoid playing in the fluky Wild Card round.

In the past 10 years, the Yankees only won the division two times. Therefore, 80% of the time over the last 10 years, 162 has been a failure.

Let’s examine this further. Cashman had a top two or three payroll in every year (except 2018). What’s the advantage of a top 10 payroll versus a bottom 10 payroll?


In 2018, 2019, 2021, and 2022, the teams with top 10 payrolls averaged 88 wins a year, while teams with bottom 10 payrolls averaged just 76 wins a year. On average, half of the teams with a top 10 payroll make the playoffs, while only 3 of the 10 teams with the lowest payroll make it (usually the Rays, A’s, and Cleveland).

Cashman is always given a top 3 payroll, and usually spending $80 to $100 million more than team #10 in payroll. The head start Cashman gets combined with the Yankees aspirations to win the World Series every year makes losing the division 8 times in 10 years unacceptable.

Fire Cashman

4) Cashman Misuse of Funds

Cashman has been around for 25 years. We can go back in history and talk about the pitching mistakes of the 2000’s – Carl Pavano, Jeff Weaver, Jaret Wright, to name a few. And on the hitting side, Jacoby Ellsbury. But let’s keep it current, to the last 5 years.

2017. Cashman knew the Yankees were going to need to reset the luxury cap. It should have been done in the rebuild year of 2017. Instead Cashman needed to be the smartest guy in the room and brought back Aroldis Chapman (after trading him for Torres) which put them over the luxury cap in a rebuilding year. Forcing them to reset the cap in 2018 instead.

2018. Yankees had to reset the luxury cap. Cashman was gifted Giancarlo Stanton from Jeter’s Marlins because Stanton had a no trade clause and had the Yankees on his shortlist.

2019. Yankees just got embarrassed by the Red Sox in October. Cashman was given 60 million to add to the payroll. Future 26 year old Hall of Famers Bryce Harper and Manny Machado were begging to be Yankees. Instead Cashman gave $17 mill to JA Happ, $13 mill to Zach Britton, $9 mill to Ottavino, $12 mill to DJ LeMahieu, and $8 mill to CC Sabathia.


Harper got $25 mill. Machado got $30 mill.

Yankees fans wanted to love the team. Instead of getting MVP players Cashman opted for bullpen and old starters.

Harper would’ve been perfect for the Yankees. Lefty. Star power. Harper said in an interview that Cashman wouldn’t even meet with him. Cashman famously said he has 6 outfielders. Those 6 include Judge. old Brett Gardner, Ellsbury (who hadn’t played in a year and wouldn’t play ever again), Aaron Hicks (who was given an extension a week before – an example of Cashman needing to be the smartest guy in the room and a bad contract), Frazier (more on him later), and Stanton, who looks like the de-facto DH.

2020. Gerrit Cole. Allegedly Cashman’s white whale (more later).

2022. Cashman has 40 million to spend. Yankees have many needs including shortstop. 3rd base wasn’t one with Gio Urshela at third. Cashman decided to take on Josh Donaldson’s 50 million dollars and get Isiah Kiner-Falefa.

The biggest issue is Cashman claimed he didn’t get Harper, Machado or any of the other young stars because the back end of those contracts are albatrosses…

… But Cashman took on 36 year old Donaldson’s off the Twins at $25 mill a year…?

Cashman did a terrible job in helping the Baby Bombers through free agency. Their offense struggled every postseason. Having a young Hall of Famer (or two) in their prime would’ve been nice.

And for that reason. Fire Cashman

5) Cashman’s Ego and Messaging

Cashman has 2 foolproof sayings that he goes to:

“Process”. This is said whenever he does a move that might be questionable at the time, or at a later date, so he can fall back on saying “the process was good”.

“Playoffs are a crapshoot”. Cashman’s way of taking zero responsibility or care to what happens in October.

Cashman enjoys being the smartest man in the room with “unique moves” that only sometimes work out. See Didi,  Clay Holmes, Luke Voit, and Wandy Peralta.

But sometimes Cashman won’t do the obvious move. The only time in the last 5 years Cashman did the obvious move was Gerrit Cole, and that that was also $324 mill.

Issue with this “process” is it trickles down to the Yankees. We saw the Yankees chill the entire second half of the 2022 season and almost blew a 15.5 game division lead.


Cashman’s “process” this year was IKF at short and Donaldson at 3rd. He never wavered. For 6 long months, and the playoffs, as Peraza raked in AAA. The Yankee players knew there was zero accountability for their terrible play, because it’s the process.

Also the messaging of “process” and “crapshoot” allows a lack of accountability that trickles down to the manager and players. That’s why you have Aaron Boone saying idiotic things like “we lost because of the roof” after Game 2 of the ALCS. Higgy and Sevy both talking about exit velo on a home run.

To cap it all off, before Game 4 a report came out that to fire up the Yankees (down 3-0) the mental coach sent clips of the Red Sox beating the Yankees in 2004 ALCS. That’s  embarrassing. The Yankees embarrassed their fans.

Cashman created this environment of excuses and lack of accountability that starts from the top and ends all the way down to the players, Making it damn-near impossible to win.

Fire Cashman

6) Cashman Can’t Develop Talent

Again. We can go back in Cashman’s 25 year history. We can talk about how he couldn’t develop a pitcher to save his life in the mid 2000’s. We can go back to Joba Rules. We can go back to not trading Eduardo Nuñez for Cliff Lee. We can go back to The Killer B’s. In fact, we can talk about 25 straight years of nothing. Let’s focus on the last 5 years, though.

2016. Cashman started the Baby Bombers. Acquired Torres, Sheffield, Frazier. Meanwhile Gary Sanchez was on his way to the Hall of Fame. Bird was the future lefty slugger. Luis Severino looked like the best young pitcher during Cashman’s entire tenure as GM.

2017. Aaron Judge hit 52 Home runs. Scrap heap finds Didi and Hicks were borderline All-Stars. Andujar and Torres emerged, both finishing top 3 in rookie of the year in 2018. Ok. The Yankees are clearly set to make a 5 to 7 year dominant run. Right??

Fast forward to 2022. Gleyber is in his 5th year, at 25 years old and is the youngest player on the Yankees!! (Until Oswaldo Cabrera came up.)

Brian Cashman had produced pretty much nothing in 4 years. Aside from no one coming up, everyone else disappeared.

Judge was elite. But everyone else disappeared. Torres fell from 38 home runs in 2019 to only 9 in 2021. Bird was injury-prone train wreck with a million excuses. Yankees never gave Frazier a chance, blaming maturity, he’s is in AAA with brain injuries.

Sanchez couldn’t catch, went through 3 catching coaches, and then forgot how to hit. Andujar got injured and disappeared. Severino got an extension, got injured a week later, and wasn’t seen for 3 seasons. Can’t even make the argument that it’s because the Yankees were winning that it’s hard to develop players.

During the Astros championship window they brought up Yordan Alvarez, Kyle Tucker,  Jeremy Peña, Cristian Javier, Framber Valdez, and Luis Garcia. The Dodgers have been winning 100 games every year. And they’ve produced Walker Bueller, Julio Urias, Tony Gonsolin, Gavin Lux, and Will Smith. Dodgers also used their farm to get Trea Turner, Max Scherzer and Mookie Betts.

Then there’s the issue of who Cashman uses his farm to get and who Cashman doesn‘t trade. Cashman used 3 top 10 prospects on Sonny Gray (more on that later). He traded high on Sheffield for oft-injured James Paxton. No complaints there, but it’s not like Paxton was amazing.


Then Cashman DIDN’T trade Chance Adams and Clint Frazier (or Andujar) for his alleged “white whale” Gerrit Cole, who went to Houston and turned into an ace. Then he liked Cole enough to spend 324 million. Traded a few top prospects for an injured Frankie Montas, who stayed injured. Last but not least Cashman gave up another two top prospects for Joey Gallo (more on this disaster later).

Here’s the bottom line. As of today the Yankees have no young players. Cashman is going to try to sell us Baby Bombers 2.0. Why would fans trust Cashman (lack of) development skills and sit though another 6 years of this? Why should an owner trust the GM he’s going to get it right this time?

Fire Cashman

7) Cashman is Behind the Curve

Once upon a time, Brian Cashman was a 34 year old man who just finished his 3rd season as the New York Yankees General Manager. All three seasons the Yankees won the World Series. Every addition Cashman made to Gene “Stick” Michael’s creation seemed to work like a charm.

2001 – 2008. We can talk about many things. George Steinbrenner meddling and trying to get the biggest stars, whether they were a fit or not. The Yankees (Cashman) inability to add pitching, so on and so forth.

2009. The Yankees added the two best pitchers – Sabathia and AJ Burnett – and the best batter available – Mark Teixeira, and the Core 4 got a ring for their pinky.

Skip ahead to now. Brian Cashman doesn’t have George Steinbrenner giving him 70% of his revenue towards payroll. Now Cashman is stuck with George’s cheap son who had the 2018 payroll lower than the 2005 payroll, despite the fact that in 2005 the Yankees raked in nearly 400 million less than 2018.

Here’s were Cashman comes in. Brian Cashman loves being the smartest guy in the room. He never got any credit for the beginning of his career when he didn’t create the core. He never got any credit during the 2000’s when George was going nuts in free agency.

Cashman always wanted to win on HIS moves and HIS signings. Since George passed away, Cashman has signed some real headscratchers (Ellsbury, Hicks and others) that reek of trying to outsmart everybody.

If you look carefully Cashman’s team building gameplan is either idiotic, or he’s just copying other successful teams.

For the entire Baby Bomber era the entire Yankee team was right handed sluggers who struck out a ton. Cashman didn’t add a competent lefty until mid 2021 (Rizzo).

The Kansas City Royals went to back to back World Series on the back of a dominant bullpen. Brian Cashman decided to pay Chapman. Then gave Britton closer money. And put a cherry on the top with Ottavino. Yankees had a ridiculous 40+ million dollar bullpen. Which seems stupid, especially since Chapman and Ottavino were playoffs bums. Britton never lived up to that hype either.


2020. The Yankees lost to the Rays,  struck out a ton, and really didn’t hit the ball much, but hit home runs. Cashman decided to “complement” that with Gallo and Odor. Good times.

Pretty much every move Boone makes, he blames the analytics department. Yet, the moves seem stupid, and the moves never work out (anyone saw the ALCS?)

Point is it’s 2022. We have an old GM who doesn’t know how to employ the latest tricks, like Cleveland, Tampa and even Houston. They’re attempting to play the imitation game to catch up. Yankees fans want a GM who isn’t from the 1990’s and can keep up with the times.

Fire Cashman

8) Cashman Coaching Troubles

When batters struggle, everyone blames the hitting coach. When pitchers struggle, everyone blames the pitching coach. Larry Rothschild was widely criticized as being an atrocious coach because not one Yankees pitcher ever got better, and many got way worse (see: Sonny Gray).

Always trying to stay fair, perhaps you put blame on Cashman for having no clue anything about pitching. To Cashman’s credit he stole Matt Blake from Cleveland and the great results were instant. Which begs the question. Why did Cashman have Larry Rothschild for 9 years?

2019. Pretty much every player on the Yankees got hurt. Cashman had to redo his entire strengthening and conditioning staff.

The thing is, Cashman is the biggest issue of them all. In 2017 Joe Garardi had the Yankees one win away from the World Series. Cashman fired Garardi for 2 reasons… He was cold with the players, and he fought with the front office over a reported resistance to fully embracing analytics.

All around the MLB, front offices were putting their puppet boys as managers. Brian Cashman wanted his own puppet. Aaron Boone was the perfect fit. He comes from a baseball family growing up in the locker room, was media the year before, and would make a great PR guy to give the media the answers Cashman wanted (Joe Garardi had wore out his welcome with the media).


There’s no problem with having a manager who is the GMs puppet. Unless the GM is making silly moves, which, as we discussed at length, Brian Cashman was.

2021. The Yankees had a subpar year. Pretty much every Yankee fan agreed Aaron Boone had a poor year, and needed to go. Boone’s contract was up so he didn’t even need to be fired. Bringing him back was the front office (Cashman) taking full responsibility for all the future terrible Boone moves.

Fast forward to this playoffs. Boone made many silly bullpen moves and lost the Yankees more than one game. The decision to hold back Clay Holmes in game 3 of the ALCS had a ripple effect we never recovered from in the ALCS (see: resisted using key bullpen pieces in game 1, Nestor hurt in game 4). We can blame/fire Boone. Or we can blame the guy who knowingly with arrogance brought back a terrible manager. Those terrible playoffs losses are 100% on Cashman.

Fire Cashman

9) Who Can Handle the Spotlight?

Which players or coaches can handle the bright lights of the New York media, the fans, and the expectations?

Brian Cashman is 25 years into his job and it’s still a guessing game for him. When he acquires a player, all he can do is pray, because he has no clue if that player can handle New York.

2017. Cashman choose Sonny Gray as the final piece to the puzzle to help the Yankees win it all. Gray was seen smiling as Yankee fans booed him off the mound after one of his terrible starts. Cashman admitted (credit to him) that Gray isn’t built for New York, and traded him for a bag of balls.

2021. Cashman grabbed two guys who failed. Andrew Heaney put up a 7.32 ERA. Honestly every Yankee felt bad for the man as he got clobbered every 4th day. Heaney cost the Yankees home field for the wild card game.


Joey Gallo. Yankees gave up a haul to bring in this guy. Long story short… He batted .159 as a Yankee (worst ever in pinstripes) while striking out pretty much every time the game was on the line. On his way out the door Joey did a tell all interview. Basically he suffered from tremendous anxiety from the Yankee fans booing him, and he begged Cashman to trade him.

We need a GM who isn’t playing a guessing game when he’s giving up a haul of prospects or hands out a huge contract.

Fire Cashman

10) Aaron Judge Fiasco

Before the 2022 season, Aaron Judge said he was willing to sign a long term deal before he hits free agency, as long as the negotiations happen before the end of Spring Training.

Aaron Judge is a top 5 face of baseball, and the only reason the Yankees are relevant. The Yankees even have a seating section named after Judge (Judge’s Chambers) behind him in right field at Yankee Stadium. Aaron Judge is the younger fans’ Don Mattingly.

Brian Cashman decided to play hardball. He didn’t start talking to Judge until a week before the season started. Judge and Cashman were very far apart. Judge wanted $35o mill, and Cashman offered $230 mill. They mutuall promised to keep negotiations private.

After they couldn’t reach a deal, Brian Cashman made a press conference basically throwing Judge under the bus, making the negotiations public in the hope the fans called Judge greedy for his contract demands. Cashman played hardball. Judge held firm. It was a gamble, by both sides.


Judge hits 62 home runs. Judge wins the gamble. But who’s the loser of the gamble? The Yankees. They could’ve locked Judge up as the face of the franchise for much cheaper than what it’ll cost now.

Now one of two things happens… Either Judge gets from the Yankees far more money than he would’ve gotten 6 months ago (meaning Cashman’s gamble will effectively cost Hal Steinbrenner and the fans $75+ million).

Or, the Yankees lose the face of the franchise and are stuck with Cashman’s boring, old, injured team.

Either way. Fire Cashman.

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Brian McNamara
1 year ago

The facts are the facts. I’ve been behind Cashman but at some point you have to stop and look at results. There’s no one single thing going wrong, and that one fact specifically means that the problem is with the guy who is responsible for the big picture. He’s had his time. He has to go. Don’t care if they fail him upwards to some executive position as long as he has no real power and is just there ceremonially. He can’t run this team anymore.

Dave Figurelli
1 year ago

That was a well thought out, factual article. Couldn’t agree more. But we all know he’s probably coming back.

Joe Tramazzo
1 year ago

This is amazing! I’m sure you could have added another 10-15 reasons more for why Cash needs to go! Ultimately IMO, there’s a lack of accountability in our org beyond the head coach & players, yet it’s our entire organization. ——- those old-time Yankee Executives (“The Establishment“) —- who are the ones pulling the strings, making the wrong decisions day-after-day, and are the root cause of so many of our issues. I suspect behind the scenes, Cash built a culture of fear and mistrust, and sadly, Hal only trusts Cashman! He’s the real fool!

1 year ago

I think I saw Hal in the parking lot wiping his a$$ with this article. Stop whining, you entitled baby.

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