The Zookeeper Is Armed

By Ethan Levine

August 20, 2026

***

"You’re in the office.  A Tuesday in the third week of January.  You’re sitting at your desk, staring at a spreadsheet on the computer, wondering how you’re going to pick up the middling sales numbers to start the year.  

Back when you were in your prime, you dominated this industry.  Top performer year in and year out.  King of the close.  Three weeks ago they made you the head of the department.  You were determined to duplicate the same success from your youth, this time from the captain’s seat.  

But then the numbers started rolling in.  They were perfectly okay.  Not great, but not an unholy disaster, by any means.  So a couple of clients had walked, who cares?  You could sense a couple more nibbling on the hook.  You had received the full confidence from the most senior leadership.  The job was yours, they had promised you, revenue dip or not.  

There’s a knock on your door.  It’s your boss, looking a tad anxious but everyone looks that way these days.  Revenue being down and all.  Can we chat real quick, he asks.  Of course, you reply.  Anything at all.  You have some ideas you’ve been wanting to run by him anyway to help give the department a boost.  The door closes.

“We’re releasing you.  Today’s your last day.  You’ll receive an email regarding severance.  Thank you for everything you’ve offered the company over the years.”  He leaves.  

Congratulations.  You now know what it feels like to be a 13-time World Series champion.

On April 28th, 1985, after just 16 regular season games, Yogi Berra was fired as the manager of the New York Yankees.  Their record was probably 0-16 or 1-15 or something.  

Wait a minute, let me grab my specs.  Looks like it was…*squints*...no, that can’t be right at all.  6-10?  Seriously?

Seriously.

If New York is the concrete jungle, then the Yankees of the ‘80s had killed the zookeeper.  They went through nine different managers in ten years, including two stints by Gene Michael, two by Lou Piniella, and the final three of Billy Martin’s five.  They tried out seven different general managers.   Their cumulative record for the decade was still, somehow, 854-708, with a World Series appearance.

George must have just liked it that way.

If the Yankees of the ‘80s killed the zookeeper, then the Yankees of today put the exhibits behind glass and have the zookeeper packing heat.  The transformation under the current brass has completely changed the way the team’s fans absorb ballgames, leading to the million dollar question:

Why do Yankees fans always seem so frustrated?

While multiple eras of George Steinbrenner’s reign were flush with championships, significant segments of his ownership were characterized by chaos.  Fans love saying, “If George were still alive…,” at the slightest moment of present-day dissatisfaction.  Admittedly, I am as guilty of that as anyone.  While such fans may be intentionally selective regarding which eras of George they choose to apply that hypothetical to, they still have a valid point.  Over the last 20 years, the New York Yankees’ front office have done their best to remove any even remote perception of volatility.  Somewhere in that transition, balanced and reasonable consequential accountability became collateral damage.  

Of course, the volatility was real.  I joked before that George Steinbrenner must have liked it that way, but Billy Martin wasn’t hired and fired five separate times because George enjoyed the paperwork.  Thirteen unique manager stints in a decade wasn’t part of a philosophy, but rather a fever.  

No one’s fate embodied that fever more than that of Dick Howser.  After managing the Yankees to an AL East title and a major league best 103 wins in 1980, they got bushwhacked in the ALCS by George Brett and the Royals.  Three weeks later, Howser was out.  

The Yankees hadn’t finished in last place, or even had a losing season.  They had completed what many organizations would still consider today to have been a dream season, but it wasn’t enough for Howser to survive one bad series against a team that was simply better for three games in October.  The Yankees’ performance was irrelevant.  All that actually was relevant was how George felt on a given Tuesday.  

(For what it’s worth, at the news conference announcing Howser’s departure, Steinbrenner’s explanation was that he didn’t fire the man.  Rather, as the New York Times reported, “Ostensibly, Howser had decided to go into the real estate business in Tallahassee,” with Steinbrenner adding, “I think it’s safe to say that Dick Howser wants to be a Florida resident year round…”  Nobody bought the explanations in 1980 and there’s no reason to buy them now.)

The doors began revolving for the next fifteen years.  You could almost see the logic behind it after the team went thirteen straight seasons without a playoff appearance (1982-1994).  But then Buck Showalter guided the Yanks back to the postseason in ‘95, getting arguably the franchise’s worst monkey in its history off its back.  The Yankees took the first two games of the ALDS in the Bronx before Seattle stunned them in the subsequent three.  It wasn’t the exact same kind of loss as Howser had experienced in 1980, but the shock level of watching Ken Griffey, Jr.’s mad dash in Game 5 was similar.  Once again, a manager had accomplished what would have granted any other manager in any other organization, past or present, an extension.  

Also once again, Steinbrenner didn’t readily acknowledge he had let go of his skipper.  He had quietly insisted that Showalter, if he cared to continue negotiating his next contract, dismiss hitting coach Rick Down.  Believing that doing so would result in losing credibility with his players, Showalter rejected the terms and that was it.  The Yankees publicly claimed that Buck and the brass had found themselves locked in a contract dispute but, like with Howser, everyone could tell what had really gone on.   

Brian Cashman joined the Yankees’ minor league scouting department in 1986 as a 19-year-old college intern, right as George was blowing through five general managers in five seasons.  Hal Steinbrenner began dipping his toes in the family business, not only as Showalter was locating the exit, but also while his father was returning from a two and a half year ban for hiring a gambler to dig up dirt on Dave Winfield (that’s a whole article for another day).  Cashman gradually finessed his way up through the ranks, from the baseball operations department, to Assistant Farm Director, to Assistant General Manager, until finally being offered the GM’s role in February 1998.  At just 30 years old, he became the second-youngest general manager in MLB history.  And as the senior Steinbrenner’s health began to fade in the mid-2000s, Hal assumed the role of chairman and managing general partner of Yankee Global Enterprises.  In November 2008, the Major League Baseball owners formally approved the transfer of primary control of the Yankees from father to son.  George Steinbrenner ultimately passed away on July 13th, 2010, nine days after his 80th birthday.  

Two men now held all the reins.  Two men who had both come of age within George’s…system.

Hal and Cashman changed how the New York Yankees view personnel to such a degree that it made fans begin to wonder if this was actually the same organization.  In all honesty, though, the duo possess a real argument to be made in favor of how they have handled business.   

Imagine you had grown up in the quaint suburbs surrounding Cincinnati.  You idolized the Big Red Machine, with mammoth prints of Tony Pérez and Charlie Hustle adorning your bedroom walls.  In more recent days, you had fallen asleep dreaming of Barry Larkin and Eric Davis’ latest heroics (and let’s not forget Paul O’Neill, of course).  

But then something changed.  The team entered a downturn, and what followed was a dose of what could be called “1980s Yankees Lite.”  In the last thirty years the Reds have had twelve different managers and six different men running the front office (either as President of Baseball Operations or General Manager).  In that whole time, with all of the turnover, all of the regime change, the Cincinnati Reds organization have not had a single NLCS appearance, much less won a ring.  

Just as the Yankees of the 1980s and early ‘90s were, the Reds have been an exemplary case study that having a shorter leash with your leadership doesn’t guarantee titles.  If it did, downtown Cincy would have had a parade by now.  And while Cincinnati still searches for that perfect team of wayfinders, over the same thirty-year span the Yankees have had just three managers and two general managers (the latter for the last 28 years).  If you consider just the period since Hal took over the team, those numbers drop to two and one, respectively.  

In those last thirty years, under some of the most unchanging leadership of any sports organization during that time (shoutouts to the Pittsburgh Steelers and San Antonio Spurs as well), the New York Yankees have had a winning record every single season, only missed the postseason five times, and won five championships.  Since Hal took over, they have missed the playoffs four of those times and won a single ring.  But by the measure of many other sports franchises, saying it has been anything other than a rousing success story would be disingenuous.

Absolutely, the Yankees have won a lot of baseball games and a lot of playoff series under Hal, Cashman and Boone.  The unsatisfying reality for the frustrated Yankees fan is that these things are all 100%, indubitably true.  You can’t dismiss them.  We fans are spoiled. The problem for the current Bronx brass, however, is that pointing this out does not address the Yankees fan’s primary concern.  It addresses something very real, but very different.

On the morning of May 31st 2023, the Yankees had just wrapped up a four-game winning streak.  In the final three of those wins they had scored a combined thirty runs, and their record in their last twenty-five games was 17-8.  On that morning’s broadcast of Boomer and Gio on WFAN, co-host Boomer Esiason said, “I don’t hear anybody bitching and complaining about Brian Cashman these days.  Nobody’s calling in and complaining about Brian Cashman right now.”

That’s not the point, though, Boomer of yesteryear, and never has been.  To the Yankees fan, it’s never been about a single winning or losing streak here or there.  It’s the often unspoken, longer-term anxiety over what has clearly become organizational dogma.  (The Yankees would actually get shut out that very night, 1-0, and miss the playoffs that season while finishing just a single win above .500.).  And Hal and Cashman have consistently been explicit in communicating that dogmatic commitment to the public. 

Two years earlier, the Yankees were completing a practically .500 first half, with calls for Boone’s job percolating.  On July 1st, 2021, in a videoconference with reporters, Hal Steinbrenner addressed the murmurs by citing what he believed was Boone’s key managerial skill, saying, “I am aggravated, frustrated, angry, but that's not going to push me into a knee-jerk reaction to get rid of somebody that I believe the players respect, want to play for, want to win for and, overall, has done a good job keeping that clubhouse together through these difficult three months.”  

That’s quite a change from how his father would have likely viewed the situation.  George’s legacy clearly hung over the press event and the junior Steinbrenner recognized this, further adding, “Look [my father] certainly [got rid of people] a lot.  I think what people forget is that, oftentimes, it didn’t help, it didn’t work.  And oftentimes, quite frankly, he was criticized for it…Doing knee-jerk reactions to appease this person or that person in the middle of the year, when I really don’t think there’s a problem, that’s certainly something I’m not going to do.”

Neither is it something Brian Cashman is going to do.  

On July 9th, 2023, the Yankees were stuck in an offensive swoon while waiting on Aaron Judge to return from injury (sound familiar?).  Since Judge had crashed into the right-field bullpen gate at Dodger Stadium on June 3rd, tearing a ligament in his right big toe, the Yankees had registered the lowest batting average and on-base percentage, as well as the second-fewest runs scored, in all of baseball.  Cashman proceeded to take what sounds, on its face, like a fairly reasonable, run-of-the-mill response to such rank mediocrity: he dismissed hitting coach Dillon Lawson.  Totally, completely, incontrovertibly normal.  The unavoidable curiosity regarding the move was that it was the very first time in his entire tenure as GM (25 and a half years at that time) he had fired a member of the coaching staff mid-season.  

“I came up in an organization that made changes in-season constantly,” Cashman acknowledged.  “It has been well documented that I have been reluctant in the past to make changes to our coaching staff in the middle of a season…It’s not something I’ve gravitated to in my tenure.”

In that moment, Cashman nearly won himself an ESPY for Understatement of the Year.

It took a historically poor (by Yankees standards) five weeks of offense to get Dawson axed.  And while it’s legitimate to value a steady clubhouse, that legitimacy only hangs on provided it doesn’t prevent you from doing the work that needs to be done.

During the August 14th, 2026 broadcast of The Michael Kay Show on ESPN, Kay announced his belief that it was finally time for the Yankees to bench Jazz Chisholm, Jr. in favor of Jose Caballero.  Jazz’ “walk year” has been disappointing in a variety of ways, and Kay employed the adage that doing something over and over again and expecting a different result is the definition of insanity.  However, “There’s also a little bit of a danger if you sit him down [that] you lose him completely,” Kay warned.  “Remember when they didn’t start him against Garret Crochet in the first game of the Wild Card [Series] last year?  He pouted like you wouldn’t believe it.  He’s a very sensitive kid, and his feelings are going to be hurt if you don’t play him.” 

Remember that Hal Steinbrenner quote from back in 2021, when he specifically lauded praise on Boone’s ability to “keep that clubhouse together” in difficult situations?  When faced with a question that was implicitly asking what the justification was for Boone keeping his job, Steinbrenner did not jump to what a brilliant tactician his manager was.  He went straight to his skill with “the room.”  Well, kindly pardon my follow-up question:

If you can’t employ your manager’s alleged biggest skill to sit a struggling player and still keep him engaged (because of the potential “danger”), then what is that manager there for?  

The answer is, To project an image of steadiness and continuity at all times.  One mustn’t, however, confuse stability with paralyzation, and there is a history of even very recent teams the Yankees can learn from who succeeded at identifying the distinction.

On June 3rd, 2022, the Phillies had a record of 22-29, including 5-12 in their last seventeen.  They sported a record payroll, and all they had to show for it was a twelve-game deficit in the National League East.  So manager Joe Girardi was sacked.  Rob Thomson assumed the helm with interim status and guided them to a 65-46 finish.  They snuck into the playoffs as the final seed, lunging a single game ahead of Milwaukee to claim the berth, before embarking on a miracle run to the Fall Classic.

How about another illustrative example from just this season?  The Red Sox removed Alex Cora from his post after just twenty-seven games and a record of 10-17.  Five coaches were also given the boot alongside Cora, including, get this…Dillon Lawson.  Since then, under interim manager Chad Tracy and an assortment of new staff, the New England Foot Apparel Baseball Co. have come roaring back into the second wild card position (as of the penning of this piece), including going on a 27-3 winning streak.  They didn’t just get hot.  They got volcanic.  

(Finally, I'd be remiss if I neglected to bring back around the ‘85 Yankees, the ones who sent Yogi packing on April 28th in favor of Billy Martin, Part IV.  Under Martin, the Bombers went 91-54 for the duration of the season, the best record in the American League during that span.  They fell two games shy of reaching the playoffs, courtesy of the Blue Jays.)

George Steinbrenner was in a galaxy all on his own, but consider the controversial decisions the other more recent front offices made.  In each case you had a veteran manager with a multi-year stint at the helm of his club.  And, hardly as an afterthought, each man had won a title as a manager.  There was ample justification to be had for keeping both men in their posts.

Now, ask yourself the following: Would we accuse either of these front offices of making chaos-provoking moves?  Or was it the rational acknowledgement by each front office that the natural time had come for a leadership transition in an effort to give a reeling roster a jump-start?  Perhaps both clubs realized that sustained underperformance, even from people with legitimate track records, eventually costs somebody something.  In both cases, it seems to have worked.   

It could certainly work for the New York Yankees as well, although Brian Cashman has given a strong indicator not to expect anything of the sort anytime soon.  Time and again, in interview after interview, he has inadvertently given fans a picture-perfect glance into the psyche behind the front office’s most hushed deliberations.

After the Yankees were swept by Houston in the 2022 ALCS, Cashman said to reporters, “People don't get let go because of results. If they have a good process, and they're doing the job well, and they have sound answers and reasonings, and the ultimate outcome doesn't happen, I think that's taken into account…"

On November 7th, 2023, from the General Managers Meetings in Scottsdale, Cashman turned a routine press availability into a now-famous twenty-minute firestorm.  Speaking on an 82-80, postseason-less season, Cashman ranted, “I know what happens when you don’t do well…I was here during the mid ‘80s, into the ‘90s…we didn’t start hitting our stride until ‘95…I remember being…with a lot of great baseball people and teams that did not perform well and the finger-pointing that takes place in a losing situation…”

And, finally, he gave perhaps his most revealing quote of all in a sit-down interview with the YES Network at the 2025 Winter Meetings.  Quoth the Cashman: “I never wanted to be GM of the New York Yankees, I’ll be honest.  It was a very tough environment and GMs under George Steinbrenner didn’t last very long.  It was a year, year and a half, maybe two, tops.  And it was a difficult situation, no doubt about it.  George Steinbrenner was a tough boss.  He didn’t have much patience…I remember more of the times, as I was working my way up the ladder…witnessing what [all the Yankees GMs of the late ‘80s and early ‘90s went through], and I would say to myself, reflecting ‘I would never, ever want to do that, because it’s no-win.’”

It’s easily imaginable that this “no-win” existence is something Brian Cashman still keeps at the forefront of his approach, and its dormancy is likely a prerequisite for his remaining in his position (as long as Hal gives him, seemingly, a lifetime appointment).

That’s all completely fair, but here’s the thing: by and large, Yankees fans agree with Hal and Cashman.

They don’t want George back.

They don’t want the real volatility of the ‘80s.  They want the credible threat that failure comes with a cost.  A cost beyond a hitting coach once every quarter century.  There is a middle ground other organizations have successfully engaged, as any respected company in any industry would be expected to.

It’s not a question of, “Can Hal, Cashman, and Boone build a winner?” 

It’s, “Will it matter if they don’t?”

I now hand the question to you, dear reader.  What do you think it would take to see some consequential accountability within Yankees leadership, particularly at the manager or general manager level?  And, as always, thank you for reading!"