The Yankees Season Ended In Failure For The 16th Year In A Row - What Went Wrong And How Do They Fix This?

The Yankees just completed their 16th consecutive season without a championship. Their World Series drought extends back to 2009. For the second straight year their opponent has celebrated on their field after eliminating them from the postseason. Yes they make the playoffs, most of the time, but postseason failure has become a constant with this organization. Kids will be entering high school now who have never seen this team lift the World Series trophy. Think about that. 

So what went wrong with this team? How can they fix this? Let's dive in…

What went wrong this season

Unlike the end to the 2024 campaign where the Yankees shot themselves in the foot against the Dodgers, the Blue Jays straight up were better in all facets of the game in the 2025 ALDS. The Jays dominated the Yankees in Games 1,2, and 4. If not for a great comeback, fueled by Aaron Judge's game-tying 3 run homer, the Yankees would have been swept out of the postseason. Their lineup was truly relentless and their pitching was nowhere near as catastrophic as New York's. 

The Pen

A major part of why the Yankees were not the home team this series and had to play during the Wild Card round of the playoffs was the bullpen. Countless games were lost during the regular season because of how bad this bullpen performed. Luke Weaver took a major step back from what was a stellar 2024 season. Devin Williams was a fucking train wreck until he figured things out in September. Fernando Cruz missing two months ended up creating a massive hole in the equation. Guys like Mark Leiter Jr., Ian Hamilton, Jonathan Loaisiga, and Scott Effross were useless when it came to helping the problem. If not for David Bednar I think they'd be on the road during the WC round. 

Quick aside from the sadness: My god is it good to have Bednar penciled in as the closer of the future.

Typically the Yankees are really good at finding spare parts who fit so well in the bullpen. It's like the one thing they've really figured out, and it mainly comes down to identifying what pitch is and isn't working for a struggling reliever elsewhere. Fernando Cruz was that guy for 2025, but his injury derailed things mid-season. That dude's splitter is a fucking problem for hitters. I'm thrilled he's locked in through 2028. The issue is, no one else stepped up. Devin Williams did his very best to sabotage the summer. I'm glad he still thought it was a special year though and that the fellas got some good stories. 

Williams is incredibly frustrating because his underlying numbers throughout the season were elite, despite the losing performances. Things began to fall into place in September. He also didn't give up an earned run in his four postseason appearances. He's the perfect candidate to bet on for a big bounce back year in 2026, but it's also tough to stomach handing him a nice sized contract after how bad things got this past season. You just know he's going to have a sub 2 ERA somewhere else next year. 

The Lineup 

Aaron Judge had himself another unbelievable season. Finally those numbers continued into October. The only problem was that no one else decided to join him. Despite very good regular seasons, guys like Trent Grisham (2 for 17), Ben Rice (2 for 11), Giancarlo Stanton (4 for 15), Jazz Chisholm (2 for 14), and Cody Bellinger (3 for 16) were not the same in October. Judge could only do so much by himself. No one else showed up beside him. It's frustrating because those guys helped make this offense a top tier threat during the regular season. 

The common denominator when it comes to the Yankees offensive struggles in the postseason is the home run or bust strategy. That method just doesn't seem to translate in October. Are homers good? Absolutely and you need a lot of them to win it all. But they cannot be the one thing you rely upon when constructing your offense. Situational hitting is paramount in today's game. Look at teams like the Brewers and Blue Jays. Hell, when Roman Anthony was healthy, watch the Red Sox. Those teams have players who are engineered to approach RISP situations differently than a nobody on scenario. The Yankees plan only seems to be mash and worry about the rest later. It doesn't change and that's unfortunately been the organizational philosophy they're hellbent on seeing through, even when it's clear the times have changed. Guess what guys? The Joey Gallos of the world aren't the ones you want on your team. Gobbling up as many well-rounded hitters as you can find is paramount. Guys who when placed in a postseason game have ways of beating you other than the home run ball. Someone who comes up with a man on 2nd and doesn't just swing for the fences. I look at someone like Ernie Clement and instead have to live with Anthony Volpe. Having that caliber of hitter at the bottom of your order who will work counts and has a plan up there is such a big boost to a team. I'm not here saying we need to sign Luis Arraez, but having guys with approaches like Anthony Volpe on your team do you legitimately zero good. It's become abundantly clear that the Yankees strategy is designed to win a bunch of regular season games, but once October comes around the music stops.  

Advertisement

Boone

The Yankees did not lose to the Blue Jays because of Aaron Boone. With that being said, he should no longer be the manager of this team. I'm not going to spend too much time on this because he's going to be back. I'd be stunned if they chose right now as the time to fire him. I don't see it. He should have been moved on from after the 2021 Wild Card loss in Fenway. There have been countless opportunities since to cut ties that were passed on because 1) Cashman/Hal love him as their scapegoat 2) the players really like him. Until either of those two change he'll be here until he's had enough. It doesn't matter that every year without fail during the summer the team regresses and resembles a bunch that have never played the sport before. It's irrelevant that he almost always gets out-classed by an opposing manager when it matters most. We can debate for hours on how much a manager matters in today's game, but I know for certain Boone does not get the most out of his guys. He does not elevate anyone's performance in that clubhouse. His voice does not motivate anyone to get better and inspire greatness. Given the expectations and talent on the roster, there is no coach in sports who would have survived this long of a title drought besides Boone. 

Cashman

Again, until Cashman wants to leave the organization he's basically got a job for life. Now compared to previous seasons I actually thought this team was constructed pretty well. Guys actually were playing their normal positions in the field (a nice change from recent years) and an actual bench was created with real MLB players. For what was available out there, Cash pivoted well for the most part after Juan Soto signed with the Mets. I thought he attacked the deadline pretty aggressively. 

This doesn't absolve Cashman from fault though. Let's remind ourselves that DJ LeMahieu entered this year on the roster and played in 45 games. Carlos Carrasco and Marcus Stroman combined to make 15 starts before it clicked in the Yankees GM's head that enough was enough. While this was an improvement on other years where guys like this would be hung onto for much longer, they still should not have been options at all in 2025. The fact that guys like Oswald Peraza, Jorbit Vivas, and Pablo Reyes were their options at 3rd base to begin the season is horrible. It was an overall improvement in roster construction and pitiful players were eventually moved on from, but it still isn't perfect. 

Offseason Plan

• Move on from Anthony Volpe. Nothing is going to happen here. He needs a reset with a different organization and the Yankees desperately must find actual production at the SS position, especially if defensive-minded Ryan McMahon is going to be your 3rd baseman. I'd rather Caballero as a bench piece who can spell guys and pinch run. I'm not entirely sure who you bring in at short but if Volpe is your guy again in 2026 that's a fucking slap in the face to the fans. Who do I want to replace him? Literally anybody else besides IKF. You simply have to make a change. 
• Cody Bellinger or Kyle Tucker? One of those guys needs to be locked up long term in pinstripes this offseason. The discourse online has been Bellinger is the right play because he'll come cheaper and is more versatile. While I wouldn't be mad at bringing him back, Kyle Tucker is the superior hitter. Bellinger just came off a fantastic 5 WAR season in New York. He fit into the lineup and the organization seamlessly. You can play him at all 3 OF spots as well as first. It's hard to gauge what his contract will look like, especially being a Boras guy and having a plethora of suitors, but you have to imagine he'll be at least a $150M cheaper than Kyle Tucker, if not more. The thing with Tucker is that he's younger and a bigger bat in the lineup. I don't think you're getting a better season than what Bellinger just gave you and that's plenty okay. But Tucker, in my opinion, has the ability to be a force next to Judge in the lineup over the next few years and then some once the Judge era ends. Keep in mind this was a down year for Tuck in Chicago and you still got a 4.5 WAR and an OPS+ of 143. Get him at Yankee Stadium for 81+ home games a year and his numbers will skyrocket. The down side is he's going to cost you upwards of $400M. The way I see it they will choose the cheaper option with close enough productivity who they're comfortable with, but the big swing of the offseason would be Tucker to me. They tried very hard to acquire him last offseason, only to realize Jim Crane was yanking their chain and was never going to actually do a remotely fair deal. Either way, you MUST get one of the two OFs. 
• I would not bring back Trent Grisham, firmly being in the camp he cannot recreate what he just did in CF in 2025 where he smacked 34 homers and was a 3.5 WAR player. Let someone else offer him a multi year deal. What I would consider is extending the qualifying offer to him and giving yourself a shot at snagging a draft pick as compensation for losing him. It's a gamble, but you gotta think someone ponies up a 2-3 year deal for him in the $50M+ range. 
•  What about Spencer Jones and Jasson Dominguez. If you've got an answer here let me know because I don't think the Yankees do. Jones will turn 25 next season. You either gotta trade the guy or give him a shot. The lefty posted a .984 OPS in 49 Double A games and an .897 OPS in 67 Triple A games in 2025. He's a good defender with speed on top of that. The strikeouts are a massive issue and terrify any evaluator taking a look at him. His power is immense, however, and makes you dream of him becoming a lefty Judge. A dream is all that is right now though. In theory he's the wrong kind of bat you should target if you're trying to change the mold of this lineup. When it comes to Dominguez, I don't know if the Yankees like this kid at all. After August 20th, Dominguez made 5 starts for the team. He received one postseason at bat, a pinch hit spot in the 9th inning of Game 4 to spare Anthony Volpe from a tsunami of boos. I believe the 22 year olds bat will develop into one you cannot take out of a lineup, but the defense needs to get better. 2025 brought on a much better sight for that than 2024. That trend needs to keep going in the right direction. Assuming one of Tucker or Bellinger are on the team, that leaves one spot for two of these kids to battle out. Does that mean one of them is traded? Either guy you'd hate to lose and watch them find success elsewhere. 
• I'd look to extend Jazz this offseason. Sure he didn't have the best postseason, but what he gives you at 2nd base is elite value. He loves playing here, brings an excitement and energy that they need, and produces. Feels like he hasn't reached his potential either and is someone who plays better when there's a true competitive environment, unlike in Miami. I want Jazz here long term and this winter is the time to lock him up. 6 years, $140M? 
• Power bats: Kyle Schwarber or Munetaka Murakami. I'll cross Schwarber off the list for us all. Even though Cash has loved Schwarber for years, where are you putting him? Stanton being the DH creates a logjam in terms of flexibility. They're not adding Schwarber to this equation. Murakami has been rumored to be a Yankee love interest for years. The 25 year old is finally being posted this winter and brings over 265 career homers in the NPB. He's a big time bat who plays first and third, although from what I've read he's gonna be an MLB 1B and that's it. If Ben Rice is the guy, and he should be, at that position then where does Murakami fit here?
• Steven Kwan. The Guardians LF is going to get traded this offseason. With two years of control left, this is the time that cheap ownership sends him elsewhere. It's what they do. Adding Kwan as the definitive leadoff guy to this team would be a 10/10 move. Want to make me happy? How about Kwan LF, Jones/Dominguez CF, Judge RF, Bellinger 1B. Rice splits time between 1st and C, as well as being an elite bench option. Bellinger mans first, but also gives you a safety net in CF if the kids don't work out. Did I just fix the Yankees? 
• If there's a good sign going into 2026 it's that starting pitcher shouldn't be much of a priority. By May or June you should have Gerrit Cole, Max Fried, Cam Schlittler, Carlos, Rodon, Luis Gil, and Clarke Schmidt as available arms in your rotation. That's insane depth. Obviously it's tough to tell how effective Cole and Schmidt will be coming off surgery, but the other options should allow them some time to figure it out and get in line for the stretch run. It's probably for the best Cole is not going to be ready for the opening series against the Giants and Raffy Devers. 

So that's a little taste of where my mind is right now. It's not the most optimistic outlook considering how 2025 ended. I'm just not sure how much you can change approach wise in such little time. There needs to be an organizational overhaul when it comes to at bat approach, situational hitting, and lineup construction. Do we see it? Probably not and I'm back here in a year's time writing the same blog as we near the start of the lockout. Fun times.