Another October Exit. The Same Questions Remain.

My frustration as a Yankees fan starts at the top.

The hardest part of watching the Yankees’ season end tonight is the familiarity. Another October disappointment, another night spent questioning the decisions that brought us here.

As a fan, my frustration starts at the top. It starts with how the roster is constructed: the free-agent signings, the trades, and the moves the front office chooses not to make. Then it reaches the dugout, where the manager decides who plays and how to navigate the moments that can determine a season.

Aaron Boone has managed the Yankees since 2018. Brian Cashman has been the general manager since February 1998. When we discuss Cashman’s legacy, we need to remember that the dynasty’s foundation was already in place when he took over. Gene Michael assembled much of that championship core, and Bob Watson helped build the team that won in 1996. Cashman contributed, but he did not construct that dynasty from scratch.

As a fan, I don’t believe those early championships should shield today’s leadership from scrutiny or give them such a long leash. How long can past success justify the same people staying in charge while familiar problems keep showing up?

Grisham Is Just One of the Latest Examples

The Yankees brought Trent Grisham back for 2026 after he accepted a one-year, $22.025 million qualifying offer. I understand the appeal of his 34 home runs in 2025. But building a roster means evaluating the whole player.

In 2026, Grisham recorded minus-six Outs Above Average and minus-five Fielding Run Value. Those numbers describe below-average defense at a position where covering ground matters. Baseball Savant

Beyond the statistics, there’s what I see watching him in center field. Too often, his approach looks lackadaisical to me. I can’t know what he’s thinking, but I can judge the urgency I see on the field—and too often, it falls short of what I expect.

Game 2 of the Wild Card Series against Boston gave me another example. In the third inning, Nate Eaton turned a shallow hit to center into a hustle double while Grisham was slow getting the ball back to the infield. Max Fried stranded him, but that doesn’t erase the extra base. To me, that play captured the lack of urgency I’ve been frustrated with all season. Boston Sports Journal

Then comes the next lineup, and he’s back out there. As a fan, I’m left wondering what changes when the same approach keeps showing up.

That frustration carried into tonight’s elimination game. Boone put Grisham in the leadoff spot, where he hit .199 during the regular season. FanGraphs

With the season on the line, how does that become your choice to set the tone? What had Grisham shown in that role that justified giving him that responsibility in a must-win game?

And guess who made the final out tonight? Grisham struck out to end the game. The final out of the season. That one at-bat doesn’t explain the entire loss, but as a fan, it was a bitter ending to a decision I had questioned from the start. Associated Press

And before we even get to Boone’s lineup, there’s the front office’s decision. How did the Yankees evaluate Grisham and decide that bringing him back at that price was the right use of their resources?

The Accountability Question Goes Back Years

My frustration with accountability goes back to Boone’s first season. Over the years, I’ve watched too many plays where the players’ effort didn’t look good enough: jogging toward first base on a groundout or showing little urgency retrieving a ball on defense.

I don’t know everything Boone says behind closed doors. But I judge accountability by whether the behavior changes on the field. When I keep seeing the same problems, I’m left with the impression that the manager is allowing them to continue.

Players have a responsibility to play hard. The manager has a responsibility to enforce that standard consistently. From where I’m watching, that hasn’t happened often enough.

A conversation behind closed doors may matter. But if the same behavior keeps appearing in front of us, fans have every reason to question whether the message is getting through—or whether that conversation even took place.

How about benching the player? Taking someone out of the lineup sends a clear message to that player and the entire team: effort is expected, and there are consequences when that standard isn’t met.

The Decisions That Stay With Me

Grisham is one example of a broader frustration.

The Yankees acquired Josh Donaldson in 2022. He hit .207/.293/.385 during his time with the team before being released. That investment left me questioning the front office’s evaluation and its expectations.

Then there was Frankie Montas, acquired despite shoulder trouble earlier that summer. He subsequently needed shoulder surgery. Injuries happen, but when a contender trades for pitching help, I expect the front office to weigh the existing risks carefully.

The questions continue in the dugout. In Game 2 of the 2020 ALDS, Deivi García pitched one inning before the Yankees turned to J.A. Happ, who allowed four runs in 2⅔ innings. I questioned whether that plan put either pitcher in the best position to succeed.

In Game 1 of the 2024 World Series, Boone chose Nestor Cortes over Tim Hill in the tenth inning. Cortes hadn’t pitched since September 18 because of an elbow injury. Freddie Freeman’s walk-off grand slam made the outcome unforgettable. But my question concerns the choice itself: why bring a pitcher back from that layoff in such a critical moment?

These decisions span different rosters and different seasons. Yet they leave me asking familiar questions about player evaluation, preparation, and judgment when the stakes are highest.

Numbers Need Judgment

Analytics have a place in baseball. I’ve used them here because they help explain what happened. My frustration is with decisions that seem to give too much weight to the numbers and too little to what is unfolding on the field.

A pitcher’s rhythm, a player’s physical condition, and the pressure of the moment deserve consideration. So does a hitter’s momentum. I understand that players need rest, but sitting someone in the middle of a hot streak leaves me questioning whether a scheduled day off is getting more weight than what’s happening on the field. I want a manager who can recognize when a plan needs to change and act before the game gets away.

Every decision carries risk. I don’t expect Cashman or Boone to get everything right. I do expect them to adjust when an approach keeps falling short.

The front office determines the roster. The manager decides how to use it. Both have a responsibility to answer for the results—and to show that the lessons from one disappointing season carry into the next.

We’ve watched familiar problems repeat, year after year. At some point, continuing with the same approach and expecting a different ending stops being convincing.

Have this front office and manager learned enough from those failures to deserve our continued trust? My answer is no. They’ve had more than enough time. The leash has been too long, and my patience has run out.

Everything starts at the top and trickles down. And when I say the top, I mean Hal Steinbrenner. He decides who stays in charge and what standard this organization accepts.

I can’t know his priorities behind closed doors. But if winning matters to him as much as the revenue this team brings in, then I want to see that commitment through meaningful changes. Keeping the same leadership in place year after year is his decision, too.

The accountability I’m asking for has to begin with him.