Yankees Thoughts: Run It Back with Brian Cashman and Aaron Boone

Here are 10 thoughts on the Yankees.

1. The Yankees’ season officially ended nine days ago, and unofficially ended on August 13 in Miami. The wild-card best-of-3 series ended last week, and today, a division series could end. All of this has happened without a word from the Yankees. No end-of-the-season press conference full of lies, excuses and empty promises. No nothing.

Then again, what is there for the Yankees to announce that we don’t already know? The lack of sourced rumors and news means there will be no changes for 2024. Brian Cashman will continue in his role for a 27th season. Aaron Boone will be back for a seventh season.

2. I’m numb to these Yankees. A year ago, I was livid when Boone was retained after the ALCS debacle in which the Yankees were swept by the Astros and he used the 2004 ALCS to unsuccessfully motivate his clubhouse. The year before that, I was irate when he was given a new three-year contract with a fourth-year option. Now? Now I really don’t care.

It’s not good for the Yankees that I don’t care. When their most ardent fans are throwing their arms up in disgust, it’s not good. I’m not alone. I have received countless texts and had countless conversations with friends, many of whom are in the same tier of me when it comes to caring about the Yankees who no longer care.

3. Once the Yankees avoided a last-place finish in the AL East and prevented the consecutive season winning streak from ending, the possibility of real, meaningful change was gone. Boone wasn’t going to survive a last-place finish, but a fourth-place finish, well that’s a whole different story! He wasn’t going to survive the Yankees finishing under .500, but two games above .500, well that’s a whole different story! The measuring stick for what is and isn’t considered a success for the Yankees has been watered down to the point that being slightly better than a Red Sox team that just fired their general manager after four seasons is enough for people to keep their jobs.

4. Joe Torre managed the Yankees for 12 seasons. In those 12 seasons, the Yankees went to the playoffs 12 times (in a format in which only the Top 4 teams in the AL reached the playoffs), won four championships and appeared in six World Series. Despite unfathomable success that led to his number 6 being retired, he was forced to sing for his supper in front of Cashman, George Steinbrenner and ownership in Tampa after three straight first-round exits. It didn’t matter that he was given an approaching-40-year-old Mike Mussina, a 42-year-old Randy Johnson, a 45-year-old Roger Clemens, Chien-Ming Wang, Shawn Chacon and Jaret Wright to navigate those postseasons. The Yankees were expected to win every season and they hadn’t in seven years, so Torre was offered a degrading incentive-laden deal to remain Yankees manager.

This week in Tampa, Boone is meeting with Cashman and ownership led by Hal Steinbrenner, who was his father’s fourth choice (at best) to run the Yankees. Boone isn’t in Tampa to sing for his supper or convince a room full of the same millionaires and billionaires that took Torre for granted in that same room 16 years ago. Boone doesn’t have to persuade the front office as to why he should still be manager of the Yankees after six unsuccessful seasons and with the organization’s championship drought now at 14 seasons with one in the last 23 years. Because to the Hal Steinbrenner Yankees, these last six seasons weren’t unsuccessful. To the Hal Steinbrenner Yankees, they were wildly successful.

5. The idea a Yankees season is a success if it ends with a championship or is a failure if it doesn’t died with George. Once the championship-or-bust mentality was erased from the organization, success was measured by simply making the postseason. “Just get in” became the motto for Hal’s Yankees and his general manager referred to the postseason as a “crapshoot” in every opportunity he could. Oddly enough, Cashman never referred to the postseason as a “crapshoot” when the Yankees were winning the World Series every year. There was no mention of success in October being “random” when Cashman inherited a dynasty built for him. Only when that dynastic roster grew old and eventually retired and Cashman was forced to build his own core did the words “crapshoot” and “random” become a part of his vocabulary.

Cashman was done the favor of all favors by the league and the players’ association when they expanded the postseason format to five teams and then eventually to six. Not only would his preaching that winning in the postseason was the equivalent to trying to win a casino game be more acceptable, but with 40 percent of the league getting a postseason berth, his Yankees would never miss the postseason. Until they did. In just the second year of seven of the AL’s 15 teams reaching the playoffs, the Yankees weren’t one of them. So the championship-or-bust measuring stick that had been downgraded to “just get in” had dropped another notch: Stay out of last place. Mission accomplished.

6. Cashman’s predecessors built him a stunning, breathtaking mansion, of which he drilled a few holes and hammered in a few nails, and then spent the next nearly three decades acting as though he built the whole thing alone with his bare hands. Once the core of players he inherited that had won four championships in five years — the five years for which Cashman still holds his job to this day — began to age and retire, Cashman couldn’t build his own core. After eight championship-less seasons, he was able to squeeze one final ring out of the Core Four by surrounding them with a half-billion-dollar offseason. Four years and a pair of ALCS losses, an ALDS disaster and a postseason-less season later, he tried the same trick, except this time his half-billion-dollar spending spree was every bit as bad as every single trade for a controllable starting pitcher he has ever made. Three years later, the Yankees had a single postseason game to their name: a 3-0 shutout loss at home to the Astros. He spent the following summer trying to convince ownership to sell at the deadline and hit the reset button, and somehow fooled everyone into thinking he wasn’t the person responsible for all the bad deals and acquisitions the Yankees were trying to sell off for pennies on the dollar.

The Baby Bombers were going to be Cashman’s legacy. They were going to prove he could develop his own talent, build a core of his own and allow him to stop living in Gene Michael’s shadow, no longer needing to pass off Stick’s work as his own. Except the Baby Bombers couldn’t turn Cashman into the genius the faction of the fan base that sleeps in Yankees pajamas so badly wanted him to be recognized as. After coming within one with of the 2017 World Series, the Baby Bombers never got that far again.

They never got that far again because Cashman’s analytically-driven organization either couldn’t finish off the development of the majority of its young players, or watched their careers stall out with no answer to fix them.

They never got that far again because Cashman continued to prospect-hug the wrong prospects only to eventually release or designate them for assignment for nothing in return.

They never got that far again because Cashman signed the wrong free agents, acquired the wrong acquisitions, surrounded his already oft-injured roster with more oft-injured players and continued to believe aging players could beat Father Time, as if it were the early 2000s and they could get help in beating Father Time.

They never got that far again because Cashman took a team that came within one win of the World Series and turned it over to someone whose managerial and coaching experience at any level was the same as mine.

7. Not only did Cashman convince Hal Steinbrenner and the executive group that offered Torre a prove-yourself contract that Boone was the right man to take over a team knocking on the door of the World Series, but he convinced them to cancel all additional interviews.

Of all the irresponsible decisions Cashman has made in tarnishing what the interlocking NY stands for, hiring Boone is right near the top. Boone proved himself overmatched for the job in his very first spring training, forgetting he needed to notify the bullpen of when to get relievers warm. In the very first series of the season, he decided to trust Jonathan Holder as if he were peak Ramiro Mendoza. In his very first postseason, his starter for the pivotal Game 3 of the ALDS didn’t know the start time for the game. When that starter could only get outs by lucking into 105-mph line drives finding gloves, Boone let him put the Yankees in a three-run hole. When that hole wasn’t big enough, Boone sent him back out for the next inning where he loaded the bases without recording an out . Needing a strikeout, Boone went to his least likely option in the bullpen to generate a strikeout. The Yankees would go on to suffer the most lopsided home postseason loss in the team’s history that night. The following night, Boone let his fatigued starter face the opposing lineup in its entirety a second time because he liked the matchup of his starter against the 9-hitter. The Yankees’ season ended that night with Boone nonsensically defending his thought process.

The process isn’t as important as the results for the Hal Steinbrenner Yankees. Cashman told us all exactly that a year ago at the team’s end-of-the-season press conference. The same press conference they have yet to hold this month. And because the process is what matters, and not scoring more runs than the opposition and not winning games and championships, there’s truly no goal for the Yankees. A process is a subjective thing. Cashman may think Boone’s process is outstanding. Someone else (anyone else) may not. Wins and losses aren’t subjective, and because of that, they’re not necessarily part of the internal process the Yankees believe they have perfectly concocted, the same way the organization said their 2022 internal metrics proved Isiah Kiner-Falefa was one of the best defensive shortstops in the league. (I guess they stopped believing in those numbers in the postseason when they benched him for his defense against the guardians and Astros.) Boone’s process hasn’t changed since his first season as a major-league manger. He made the same in-game strategic mistakes in 2023 he made in 2018. Shockingly, the Yankees have only grown worse during his tenure, operating under his process.

From top to bottom, the Yankees are a mess. Their majority owner wants no part of owning the team. He wants to reap the financial benefits of being an all-time lucky sperm, but doesn’t want to do any of the work involved in earning those benefits. His hands-off approach has kept Cashman in power, and the cocky, stubborn smartest-guy-in-the-room, who five years ago rejected the idea of Bryce Harper being a Yankee, continues to operate with no accountability or consequences. Do you really think the guy who didn’t even meet with Harper during his free agency because he had an outfield depth chart of Aaron Judge, Giancarlo Stanton, Aaron Hicks, Jacoby Ellsbury and Clint Frazier or the guy who watched Josh Donaldson’s 2022 and then brought him back and rostered him for nearly all of 2023 is going to admit to any wrongdoing in his hiring of Boone. Because that’s what moving on from Boone would be. It would be an admission that choosing the guy with no experience was the wrong choice. We’re talking about the same guy who was forced by ownership to call up the kids in August and September against his wishes. If it were up to Cashman, Donaldson and Harrison Bader would have still been batting fifth and sixth for the Yankees last Sunday.

8. Steinbrenner has Cashman’s back. Cashman has Boone’s back. Boone has his players’ backs. And his players say they have Boone’s back because what else are they supposed to say? Judge could think Boone a moron (which he is) and do you think the captain of the team is going to tell a sea of microphones his true feelings about his manager? And yet, Judge’s supporting his manager to the media at the end of the season is being used as some sort of proof that none of the Yankees’ failures are on Boone. Boone losing his job wouldn’t be scapegoating. He’s not a scapegoat. He’s not the problem, but he’s a problem and part of the overall problem, and has been since he was hired. The goal for the organization should be to resolve all problems.

In all likelihood Judge and Gerrit Cole and all of the Yankees love Boone, and why wouldn’t they? Everyone wants a boss who is their friend first and authority second, if at all. Everyone wants a boss who doesn’t care about mental, physical or emotional mistakes, who holds no one accountable and has little care for results.

Boone is a dream boss. He’s the ultimate player’s manager. Make the first out of an inning at third? He likes the aggressiveness. Give up seven runs in two innings? He thought the stuff was great, but there were just a few pitches the starter would like to have back. Jog down the first-base line like you’re a valet attendant retrieving a car? He’ll say he believes the effort was there. Blow a kiss to heckling fans who are fed up with a soft, thin-skinned $800,000-per-start pitcher? He’ll say at least the pitcher in question didn’t physically assault the fans. Turn your back on the pitching coach after allowing eight runs without recording an out? He’ll say he would have disciplined the pitcher in question, but it’s late in the season.

There’s no ceiling for the lengths Boone will go to “protect” his players. But in doing what he thinks is protecting is his players, all he has really done is create a losing culture for the winningest organization in sports history. He has created a clubhouse and roster that is comfortable with losing and that believes there’s always tomorrow. And why wouldn’t they? That’s all any of them have heard since becoming Yankees under Boone. The only player still around now to remember how things were before Boone is Judge, and maybe that’s why Judge referred to the season as a “failure” two weeks ago, something his manager or teammates wouldn’t dare to do.

9. With no change at general manager and no change at manager, what change is coming for a team that just finished 19 games out in the division? How are they planning on closing that 19-game gap? They aren’t. The only movable player on the roster is Gleyber Torres, and while I’m not the biggest Torres fan, it’s probably not a great idea to trade the team’s second-best hitter. (I fully expect the Yankees to keep Torres, not extend him and then lose him to free agency a year from now.) The rest of the roster is a collection of young players you can’t trade out of necessity, young players whose trade value has decreased now that they have reached the majors with little-to-no success or mid-to-late-30s players owed big money. The free-agent market looks like a tag sale of items that belonged to an owner who was a chain smoker.

10. That leaves the Yankees with one option for next season: another massive parlay. Hope DJ LeMahieu gives them a full season, Stanton isn’t officially washed, Anthony Rizzo can avoid long-term concussion symptoms and be productive, Anthony Volpe isn’t a bust, Jasson Dominguez returns in July looking like he did in September, Carlos Rodon can stay healthy and pitch to his salary, Nestor Cortes can bounce back from shoulder problems and that Michael King and Clarke Schmidt can build on their 2023 seasons. And on top of all that, they need Judge and Cole to continue to perform at a superstar level. Easy.

It’s a lengthy parlay card that looks every bit like the offseason parlay cards the Yankees have created for themselves over the last decade. If A, B, C, D, E, F, G, H, I, J and K all happen, this could be a World Series team! None of those parlays hit and don’t expect this one to either.

No change at general manager. No change at manager. No change to the roster because there’s no change to be made.

They’re really going to run it back. Again.