Why parting with Brian Cashman may not be best for Yankees

If you want to fire Brian Cashman right now, I understand. I think you can make a case built around, particularly, Cashman not maximizing the draft and international signings.

Cashman famously said in December 2018 — between the Yankees’ loss to the Red Sox in the Division Series and the organization’s decision to not sign Bryce Harper or Manny Machado — that when it came to baseball operations, “We’re a fully operational Death Star.”

But they aren’t. They have not hit enough in the draft, with international signings or by developing the prospects they do have to a level of, say, the Astros and Dodgers. Yes, they draft late every year because of regular-season success, and their international pool of money is curtailed by rule. Still, even with those obstacles, there are not enough success stories. Is that the result of procurement, development or both?

A fully operational Death Star does not lose talented arms such as Trevor Stephan and Garrett Whitlock for nothing in the December 2019 Rule 5 draft while protecting Chance Adams and Brooks Kriske, not to mention Ben Heller and Stephen Tarpley (you want me to keep going?). A fully operational Death Star does not use metrics to make a case that a team can win a championship with Gary Sanchez catching and Gleyber Torres at shortstop because, if so, it is using the wrong metrics and/or interpreting them incorrectly and/or just not paying attention to the reality in front of them.

But every organization can count a similar number of mistakes — and usually lots more. Remember, for example, when you watch the World Series that the Dodgers once traded Yordan Alvarez for Josh Fields. Houston built a sustained run of excellence despite — among other things — drafting Mark Appel rather than Kris Bryant with a first overall pick, releasing J.D. Martinez and trading Josh Hader for Carlos Gomez.

No organization — even the best — gets close to every decision correct. The reality is, for a quarter of a century, Cashman’s department has done exceedingly well at keeping a high-level contender in play. Let’s use 3Up to make a case for keeping Cashman that begins with a telling number:

Trevor Stephan pitches on Friday during the Guardians' Game 2 win over the Yankees.
After being left unprotected by the Yankees in the 2019 Rule 5 draft, Cleveland’s Trevor Stephan faced them in this year’s ALDS.
Getty Images

1️⃣ Seventeen. What does 17 represent? That is how many games the Yankees have played while mathematically eliminated since Cashman became the GM in 1998. Seventeen. Really, it is a staggering stat. The 17 come from the only four years the Yankees have not reached the postseason under Cashman’s watch: five games in 2008, five games in 2013, four games in 2014 and three games in 2016.

That also means they were in play for a postseason spot even late into those years and never sank below .500 or to irrelevance.

If your knee-jerk reaction is to mention that with the kind of payrolls the Yankees sport this should be par, well, the Red Sox, Angels, Cubs, Mets and Phillies (among others) have often had huge payrolls and horrible results.

The Mets, for example, have run through a lot of general managers during Cashman’s tenure, and at the moment of change, it was always good riddance to the old guy and optimism about the new guy — until the new guy began to also fail. Which brings us to …

2️⃣ Who would replace Cashman? These are the Yankees. Before you get rid of a remarkably successful current employee, you better be damn sure you have an idea that someone you really believe can do better is available. Theo Epstein isn’t taking the job. Alex Anthopoulos and Andrew Friedman are under contracts. David Stearns stepped down from Brewers GM to advisor. Perhaps he is available, except he just made a worse trade of Hader than his former Astros boss did. Oh yeah, his former Astros boss is available. That would be Jeff Luhnow. Do you like that idea, Yankees fans? The guy who was the GM during the Astros sign-stealing scandal taking over baseball operations?

Houston Astros' Jeff Luhnow answers a question during a news conference to announce his promotion to President of Baseball Operations and General Manager Monday, June 18, 2018, in Houston.
Former Astros general manager Jeff Luhnow is available, but would bring the baggage of his involvement in the Astros’ sign-stealing scandal.

Consider the decisions made by two very successful franchises after the 2019 season. The Red Sox and Astros each were looking for a top baseball executive. Boston had dismissed Dave Dombrowski. Luhnow had been fired by the Astros for either just cause and/or to scapegoat him so ownership did not have to take the brunt of the criticism for the cheating scandal.

Both teams decided to pick someone from the well-regarded Rays baseball operations department.

Houston picked James Click, and in his time, the Astros have won three division titles. They were ousted by the same Rays team that had just eliminated the Yankees (2020), went to and lost the World Series in 2021 and are back in the World Series again. You know what this reminds me of to a significant degree? How Cashman came into his job.

Bob Watson left after the 1997 season, and Cashman was promoted from assistant GM. His greatest asset was a willingness to not feel he had to put his fingerprints all over a good thing. He inherited a championship core and rode it to three straight championships from 1998-2000 — making moves along the way (Orlando Hernandez, Roger Clemens, David Justice) that helped keep the elite motor humming. Click basically took over the same kind of operation from Luhnow, and smartly has not messed much with the core while improving the overall product.

Still, he might lose his job in the offseason because the belief is owner Jim Crane does not have much affinity for Click. These are difficult jobs to get, do well in and then keep.

Boston picked Chaim Bloom, who in his three years has seen the Red Sox finish last twice and lose in the 2021 ALCS to Click’s Astros. One of those last-place finishes was this season, leaving the Red Sox with little to show for trading Mookie Betts after having spent significant money once and what sure seems poorly on Trevor Story and having few clear high-end building blocks to build their next contender around in a division loaded with teams with high ceilings (now including Baltimore). It is possible the best success so far for the Bloom group was taking Whitlock away from the Yankees in the Rule 5 draft.

The guy Bloom replaced, Dombrowski, has the Phillies in the World Series. Dombrowski also is not available to the Yankees.

General manager James Click of the Houston Astros
James Click has helped guide the Astros to three straight AL West crowns and an appearance in this year’s World Series, but his frosty relationship with team owner Jim Crane has put his job in jeopardy.
Getty Images

If Hal Steinbrenner had decided after the Yankees lost the 2019 ALCS to the Astros to replace Cashman, would his choice have been Click, who might be out of a job soon? Or Bloom, who does not seem to be maximizing large resources in Boston? Remember, these were once hot candidates.

The idea that the next guy will be better than someone whose team has played 17 meaningless games — 17!!! — in two-plus decades is doubtful.

3️⃣ Winning is tough. I know fans don’t want to hear that. The Jeter dynasty Yankees, in particular, spoiled them, and George Steinbrenner created the championship-or-bust mentality that persists today and makes all the postseason endings play like misery.

Keep in mind, though, that from 1982-93 (1994 was a lockout year), the Steinbrenner Yankees did not make the playoffs once and spent most of that time as the laughingstock of the sport (the inconvenient truth for every person who offers, “This wouldn’t be happening if George were still alive”). The Yankees won one title in the final 14 seasons of Jeter’s career (yep, those coincide with Cashman as the GM).

The Dodgers, more than any other team, are held up as the model of a well-run organization these days. Yet, that organization has won one title since 1988 — and that came in the shortened pandemic year of 2020. As great as the Astros have been, if the Phillies upset them in this World Series, Houston still will be holding at one title in its history — that in a season when the Astros might have had every team’s signs illegally.

So why aren’t the Yankees more like the Phillies? You mean the same Phillies who had the longest NL playoff drought (since 2011) going into this season, a drought that included their first three years with Bryce Harper? Remember, if the union had turned down the playoff format changes in the new CBA and the setup remained the same as last year, the Phillies wouldn’t have made this postseason as the sixth seed — because there would be no sixth seed. It is also possible that if the Brewers didn’t trade Josh Hader, they would have finished with a better record and the Phillies still wouldn’t have made the playoffs.

Members of the Philadelphia Phillies celebrate after defeating the San Diego Padres in game five to win the National League Championship Series at Citizens Bank Park on October 23, 2022 in Philadelphia, Pennsylvania.
The pennant-winning Phillies reached the playoffs only after an overhaul of the postseason format.
Getty Images

That would have continued what was (forget the lovefest happening now) pretty much a season-long criticism of a Phillies team that had so many of the shortcomings of recent Yankees squads — notably heavy reliance on homers and range-challenged defense.

Look, we make the narratives fit our arguments. The Phillies went from wasting a lot of money while never making the playoffs to spending it well. It helps with the cheap Hal Steinbrenner chides. If only the Yankees, who spent the third-most on payroll this year, had spent similarly to the No. 1 and No. 2 teams, the Dodgers and Mets. Oh wait, the Dodgers and Mets combined for as many postseason wins this year (two) as the Yankees had by themselves.

Again, if you want to get rid of Cashman, there is a case that is not caked in the overheated fury of a spoiled fan base not getting a parade — that this front office might have a staleness to it that demands another voice to see whether the Yankees can be piloted not just to, but through the playoffs.

But I talked this week to a former longtime employee of the Yankees. This person likes Cashman, but is not a blinded loyalist. He pointed out a reality many overlook: “You guys [reporters] and fans have no idea of the [bleep] the GM of the Yankees has to deal with behind the scenes,” the former employee said. “You have no idea how heavy the weights of expectation are inside and outside the Yankees compared to everywhere else. You have no idea the kind of personality and skill and deftness it takes to deal with it all. And Cash is really good at dealing with it all.”

This is not the only person over the years who has told me a version of this. It is something I always think about when the torches and pitchforks come out to fire Cashman and just hire anybody else without attaching a name and a personality and a track record to that person. Cashman is not a Supreme Court judge. He should not have a job forever without question. But these are the Yankees, and you need a much better plan than “anybody else” to replace him.

New York Yankees owner Hal Steinbrenner, left, general manager Brian Cashman, center, and Aaron Boone, pose for photographers during a news conference introducing  Boone as the baseball team's new manager, Wednesday, Dec. 6, 2017, at Yankee stadium in New York.
Working for Hal Steinbrenner and the Yankees means navigating expectations few other GMs face.

Of course, the reality is that Cashman’s contract is up. And while I am not sure that Mets owner Steve Cohen is going to bid on the Yankees’ headline free agent, Aaron Judge, I think if Cashman is not re-signed by Steinbrenner in the next few weeks, Cohen would be very interested in making Cashman Billy Eppler’s boss again. As another executive told me this week, “If Brian were out on the market, he’d have offers in five minutes.” This executive added that the industry holds Cashman in much higher esteem than the media who cover and the fans who cheer for the Yankees.

So do I think Steinbrenner should bring Cashman back? I do. And I think he will — because owner comfort is as important as any factor in who gets hired/retained or not (just look at the successful Click’s uncertain status in Houston for an owner who doesn’t seem to have developed a strong relationship with him). Steinbrenner is a licensed pilot — i.e., someone with experience at viewing matters from 20,000 feet — and as opposed to his father, he likes to take a deep breath or three away from his most emotional moments before making a decision. That reflection will remind him that he trusts Cashman. That he knows Cashman has kept his team among the best in a competitive industry. And, ultimately, Cashman is delivering a plan based on the short- and long-term budgets authorized by Steinbrenner.

Still, I think Steinbrenner also needs to ask hard questions about the draft and international free-agent market and player development and whether the Yankees are doing a good enough job of landing amateurs and maximizing their skills while in the minors. He should ask if part of the now annual October malfunction has to do with being unable to suppress the championship-or-bust mentality and whether that overburdens the players. There is no easy solution to what, to me, is clearly an issue. But you can’t run away from it either; players are performing under extreme stress.

Steinbrenner needs to ask whether this manager and coaching staff are providing a real-time competitive edge in the postseason or are so locked into pre-game strategizing that they are not reacting well to the actual game in front of them. Are they experienced and respected enough to help a player in crisis in the crucible of October?

He needs to ask Cashman whether there is now a bit of a groupthink echo chamber in baseball operations. This is not anti-analytics. For anyone who said the Yankees were too analytical and that is why they lost to the Astros, know that the Astros are at least the Yankees equal in emphasizing analytics. But there has to be a feel, too.

New York Yankees manager Aaron Boone looks on before a game against the New York Mets, Tuesday, July 26, 2022, in Queens, NY.
Aaron Boone’s ability to adjust to the circumstances of a game in real time, especially in the playoffs, has come under more scrutiny with each early postseason exit.
Corey Sipkin

For example, Isiah Kiner-Falefa publicly admitted during the season that social media criticism unsettled him. The understanding that the pressure was only going to grow for Kiner-Falefa as the season and postseason went on is not on a spreadsheet. He was jittery in the field, often in tight games. He played too deep to avoid getting beat by grounders, which upgraded his range without his having the arm strength to justify the depth. He did not have the outstanding feel of a natural shortstop — all you needed were eyes to watch Kiner-Falefa play the position as compared to Oswald Peraza to see that one moved like a shortstop and one moved like a utilityman trying to play shortstop.

Cashman insists he listens to all areas of his operation equally and then makes a decision. But Cashman also has become a devotee of the data more than anything. It has led to lots of superb decision-making. Analytics don’t guide all, but they have helped the Yankees excel at finding talent on the margins — just think of how little they gave up for bullpen finds such as Chad Green, Clay Holmes, Michael King and Wandy Peralta — the type of players who the Mets, as a counter-example, hardly ever find.

Cashman has a strong scouting wing headed by Matt Daly, Jim Hendry and Tim Naehring. But perhaps one more person with gravitas in this area — a Doug Melvin or Brian Sabean type (both of whom have Yankees roots, by the way) — would offer even more perspective. It feels as if in the fog of the playoff war that the Dodgers and Yankees are too pre-game scripted. Those pre-game scripts are valuable, yet based on macro-data accumulated over thousands of games. Does that information line up to what actually is taking place in the singular game in front of them, though?

The best improv artisits depend on all the training done before ever stepping on stage in front of a crowd. At showtime, that training is their backbone. But then they incorporate what kind of crowd it is, what scenario they have been asked to play and how their scene partners are behaving in the moment — all stuff that is not possible to fully script. A game is a nine-inning improvisation once the first pitch is thrown.

New York Yankees GM Brian Cashman talking with Aaron Judge on the field before the game.
The futures of both Cashman and Aaron Judge will be decided this winter.
Charles Wenzelberg/New York Post

Cashman is one of the most successful executives in baseball history because, among other things, he has shown a willingness to adapt and change when it became obvious adaptation and change were needed. He is at that doorstep now. He runs a strong baseball operations department. It doesn’t need to be a fully operational Death Star. It needs to get better.