My newfound appreciation for the Yankees’ brain trust
For years, the baseball cognoscenti lauded Hal Steinbrenner as a smart businessman, a cerebral figurehead, and the diligent purveyor of the Yankees’ global empire. I just saw middling payroll-as-percentage-of-revenue figures, a 16-year championship drought, and a meek nepo baby of the indomitable George.
For years, baseball experts held Brian Cashman in similarly high regard, saying any other sports team – and many corporate organisations – would hire him in a heartbeat if the Yankees let him go. I just saw a dispassionate functionary who spent over $3 billion on player salaries chasing the twenty-eighth World Series in franchise history.
For years, sabermetricians praised Michael Fishman, the Yale brainiac who built the Yankees’ analytics department from scratch, suggesting he raised the bar across baseball. I just saw an awkward Mets fan who traded his orange and blue hoodie for the obligatory chinos and half-zip pullover of the archetypal front office nerd.
For years, draftniks and prospect gurus feted the Yankee farm system, explaining how back-end depth compensated a lack of headline talent. I just saw a string of failed cornerstones, from Gary Sánchez and Luis Severino to Joba Chamberlain and Phil Hughes.
For years, media types trumpeted Aaron Boone, calling him an excellent communicator, a dynamic players’ manager conversant in pine tar and analytics alike. I just saw a clumsy former ESPN analyst with a propensity to botch big game decisions.
And for years, analysts revered Matt Blake, the pitcher whisperer du jour who oversaw an innovative pitching lab. I just saw a geek who never played the game professionally.
I have written plenty of critical columns admonishing these guys, the collective Yankee brain trust, over the past decade. They were aloof, I said. They were myopic and stubborn. They were the definition of insanity, doing the same thing over and over again while expecting different results.
Well, I was wrong. I didn’t get it. Now, I do. And I have a newfound appreciation for this hierarchy, this institution, and its world class methodologies. I have come to Yankee Jesus, swallowed the pinstriped pill, and recalibrated my outlook on an entire era of baseball history.
“I’m proud of our people and I’m proud of our processes,” Cashman infamously told reporters in an expletive-laden rant following the disappointing 2023 season. “Doesn’t mean we are firing on all cylinders. Doesn’t mean we’re the best in class. But I think we’re pretty fucking good, personally, and I’m proud of our people.” (1)
Ultimately, after much soul-searching, I agree. At the time, coming off a fourth-place finish, Cashman’s acerbic remarks felt tone deaf. But with time, I have acquiesced to the crux of his point: the Yankees do have excellent people adhering to productive processes. In fact, they are the envy of professional sports in that domain, and those responsible – those setting the culture and driving the modus operandi – deserve far more respect than they are typically accorded.
Hal Steinbrenner, visionary moderniser
Such an ethos begins at the top, of course, with Hal, who has matured before our eyes since inheriting the Yankees in 2008 as a dazzled, 39-year-old neophyte. In many ways the inverse of his ferocious father, Hal has often been lambasted by fans and reporters for an apparent failure to uphold the trademark family impulsivity. An introverted strategist, Hal was a successful hotelier before assuming the Yankee mantle. He loved spreadsheets and prized data as a vector of pragmatism. According to Hal, the Yankees do not need a $300 million payroll to field a championship-calibre team, with analytics holding the key to efficiency.
I have often railed against that notion, deeming it a disgrace to Yankee exceptionalism, but ultimately, Hal is correct. That overarching dogma has been proven time and again, as teams with modest payrolls – St Louis, Houston, Kansas City, Washington – have claimed the holy grail since last it returned to the Bronx.
In fairness, Steinbrenner has shown a consistent willingness to spend exorbitantly to keep the Yankees competitive. That spending has often just come in unconventional or unglamorous places, unmoved by the populist clamour of giddy fans. No, Hal did not sanction spending on Robinson Canó or Prince Fielder, Bryce Harper or Manny Machado, Juan Soto or Shohei Ohtani. But he did drop historic bounties on CC Sabathia and Mark Teixeira, Jacoby Ellsbury and Masahiro Tanaka, Gerrit Cole and Carlos Rodón, Aaron Judge and Max Fried. Though unpopular, there is discernment in the Yankees’ spending, and we never get to see their proprietary algorithm.
In this regard, and many others, Hal has put his own stamp on the Yankees. And while he is commonly chastised today, from a vantage point 30 years hence, he will be remembered as a great moderniser. From christening the new Stadium with a title in 2009 to relaxing the team’s traditional facial hair policy, Hal has pushed the Yankees forward. Fans may dislike his robotic personality, but in time, they will become thankful for the measured, incremental improvements on his watch.
Indeed, for all my venting over the years, I have finally come to respect and appreciate the modern Yankees, hewn in Hal’s understated yet uncompromising vision. Hal’s Yankees are an insular, intellectual powerhouse that pursues supremacy in quiet dignity. Their shrewd modus operandi diverges from the garrulous Yankee archetype – conceived by Jacob Rupert and mastered by George – but they are building a logical foundation for sustainable long-term success.
These contemporary Yankees are insular and reticent, considerate and classy, secretive and circumspect. The enterprise has assumed the personality of its topmost leader, who cherishes academic contemplation above all else, and who would rather sit in silence than fill gaps with inane small talk.
Distinctively, the Yankees’ inner sanctum rarely accepts new members, akin to a Vatican conclave, with family-like loyalty an unspoken prerequisite. Hal surrounds himself with the best people, in close-knit privacy, and lets them implement proven processes that realise his stoic edicts for replicable excellence.
The Yankees’ unparalleled retention of executive talent affirms the quality of their methodologies and the environment in which they thrive. Throughout baseball, assistant general managers and ascendant number-crunchers regularly jump to loftier positions with other teams. Generally, though, the Yankees’ brass seems impervious to that carousel. Many top decision-makers have logged decades in the organisation, crafting strong reputations, yet they choose to stay with the Yankees, foregoing more expedient career progression elsewhere. Why? Because their work is valued, there are good prospects of internal mobility, and a stern protectiveness hones a culture of familial faith.
Brian Cashman, serial winner
Of course, no Yankee employee is more entrusted than Cashman, who joined the team as an intern in 1986, became its general manager in 1998, and is regarded as something akin to a brother by Hal. Cashman has five World Series rings encrusted with the interlocking NY, and recently passed 2,500 regular season wins as GM. Brian Sabean, a Hall of Fame executive in his own right who returned to the Yankees as an advisor in 2023, considers Cashman the greatest GM in baseball history, and there is compelling evidence to support such a claim. (2)
With Cashman in situ, the Yankees have produced 32 consecutive seasons with a winning record. A thirty-third straight finish above .500 is all but guaranteed, and we should really take a moment to appreciate that remarkable achievement, which is all too often overlooked.
Multiple generations of Yankee fans were raised to consider catastrophic any season that did not end in a parade down the Canyon of Heroes. However, even if we adjust that standard slightly – bring it more in-line with modern major league norms – the Yankees’ continued success is clear to see. A string of 33 straight winning seasons is incongruous in a parity-obsessed sport. It speaks to the Yankees doing something right – even if the ultimate October shakedown does not always go their way.
Just look at the rival Red Sox, who have logged six last place finishes and missed the postseason 14 times in Cashman’s Yankee GM tenure. By contrast, the Yankees have only been out of playoff contention in 22 of 4,300+ games in that 27-year span – a stupefying 99.5% relevancy rating. Yes, the Red Sox have claimed two world championships since the Yankees last won it all, but Boston has also chewed through six different full-time baseball heads during Cashman’s reign.
Undoubtedly, there is a fine line between reassuring consistency and stultifying stasis, but I have come to see Cashman’s ubiquity – his unparalleled experience and instinctive institutional knowledge – as a major advantage over more transient contemporaries. While years without achieving the main objective can create a sense of stale indifference, or even an ingrained acceptance of mediocrity, I contend that Cashman knows better than anybody in baseball history how to build a team all but assured of playing in October. The Yankees have only missed the postseason five times since he became GM, an 81% success rate over a 27-season period. No other team has a comparable record.
Michael Fishman, analytical mastermind
Cashman is routinely derided for an alleged over-reliance on analytics, and some of those concerns are valid. The Yankees have taken a stubborn, template approach to roster construction over the years. They have been too right-handed, too injury-prone, too unathletic and too dependent on the home run. They have deprioritised fundamentals. And undoubtedly, skewed statistical algorithms have contributed to those deficiencies, acting like a cookie cutter while identifying certain players to acquire. But I struggle to find any one egregious decision the Yankees have made solely based on analytics.
Sure, there have been disastrous acquisitions – Stephen Drew, Aaron Hicks, Joey Gallo, Josh Donaldson. And yes, analytics likely highlighted those players based on preconfigured preferences inherent in their respective resumes. But those players were not acquired on the exclusive strength of data. Undoubtedly, Cashman takes insights from Fishman, who was hired in 2005 on the recommendation of Billy Beane. (3) However, Cashman also considers views from traditional evaluators. The ratio of influence could perhaps be rebalanced, but all decision-making protocols are flawed. After all, the Yankees drafted Brien Taylor first overall in the 1991 draft, on the supposed wisdom of scouts, and he never threw a single pitch in the majors.
“People talk about us being ‘analytically-driven,’” Cashman exclaimed during his 2023 tirade. “Do you know we have the smallest analytics department in the American League East? We have the largest pro scouting department in all of baseball. Analytics is an important spoke in our wheel – there’s not one team that’s not using it – but to say we’re guided by analytics as a driver is a lie. It’s important, and we utilise it – along with our pro and amateur scouting opinions – and yes, sometimes we do better and sometimes we do worse with our decisions. Sometimes, they don’t work out, but that’s also part of the process.” (1)
To that point, for every Drew, there is a Luke Voit; for every Gallo, there is a Clay Holmes; and for every Donaldson, there is a Luke Weaver. In sum, for every doomed deal endorsed by Fishman, there is a triumph steered by his department. For every ill-advised albatross, data unearths a stealth reclamation project from the scrapheap. Baseball is a game of probabilities, and positive arbitrage – compounding incremental improvements over a long period – is the en vogue objective.
Admittedly, the Yankees’ reiteration of a metric-driven approach after each playoff setback can smack of arrogant pig-headedness. They can come across as believing their own hype, thinking they are the smartest guys in the room, fan rage be damned. However, we, as fans, only see the final product, and our fickle passion tends to conflate outcomes with processes. Maybe they are the smartest guys in the room, and leaving them to do their jobs can free us from skyrocketing blood pressure.
A more nuanced commentary separates process from outcome. And in process – in gathering, sorting and using data to make decisions – the Yankees are world class, whether we like it or not. We would all like to rekindle the glory days, hewn from the acumen of ‘baseball men’ who ‘played the game the right way’ with ‘heart and hustle,’ but such an approach is long gone. To revert to such hunches and guesses, opinions and prejudices, alone, would be to wilfully embrace intellectual atrophy. It would be a step back, not a leap forward, because more information is always better than less when making decisions.
Certainly, when those decisions are perceived to be suboptimal – when the Yankees continually fail to win the World Series – those making the decisions should be held accountable. I wholeheartedly agree, and have, at times, called for change in the Yankees’ front office. However, the very definition of a ‘suboptimal decision’ is subjective, especially in baseball, a capricious game ruled by the cruel mistress of fortune. And while Cashman’s refrain that postseason baseball is a ‘crapshoot’ feels icky, sheer luck does play a significant role in determining October champions. Attempting to map and pre-empt that unpredictability – to decipher its mercurial trends using data – is more productive than surrendering to its whims.
Matt Blake, pitching savant
Nowhere is that efficiency more readily apparent than in the organisational approach to pitching, orchestrated by Matt Blake, a savant plucked from the esteemed Cressey think tank. A former player development bod with the Cleveland Guardians, Blake had never played or coached above the Cape Cod League when Cashman hired him in November 2019. Now in his sixth season, the 40-year-old has built an innovative pitching lab that is the envy of MLB.
Blake’s system has a documented track record of identifying distressed or undervalued assets, recommending transformative tweaks, and reaping exceptional rewards. Waved by Kansas City and DFA’d by Cincinnati and Seattle, Weaver is now the Yankees’ unflappable closer. Released by the 121-loss White Sox, Tim Hill is now a dependable lefty specialist. Non-tendered by Pittsburgh, Holmes was resurrected in pinstripes before landing a three-year, $38 million deal with the Mets. Throw in myriad other case studies – Ryan Yarbrough, Fernando Cruz, Mark Leiter Jr., Nestor Cortés, Jonathan Loáisiga, Wandy Peralta, Ian Hamilton, Tommy Kahnle – and it is easy to see why the Yankees’ bullpen, in particular, is consistently fantastic.
Blake has also transformed enigmatic starters, honing erraticism into excellence. Tutored by Blake, Luis Gil won Rookie of the Year. Rodón rebounded from a disastrous start to his Yankee tenure to become a monstrous co-ace. Michael King went from a marginal swing guy to the centrepiece of a Juan Soto trade. And Domingo Germán threw a perfect game. Right now, Will Warren is maturing and adjusting, coaxed by Blake, while Devin Williams is following a similar path. In short, you never have to worry about the Yankees finding enough outs. The more ammunition Blake receives, the greater results he delivers.
Yankee finishing school
To Cashman’s point, then, and to the consternation of devout detractors, the Yankees do have excellent people throughout their organisation. That extends to scouting and development, where Damon Oppenheimer, Tim Naehring and Kevin Reese have established a finishing school for good people, not only good ballplayers. And that is also something to be proud of.
Critics quickly point to failed Baby Bombers like Sánchez, Severino and Greg Bird, but advocates can highlight many successes, as well, headlined by Aaron Judge, one of the greatest players of all-time. There is now a discernible culture embodied by matriculating pinstriped farmhands, a tangible Yankee Way – a code of values, behaviours and characteristics – that defines their approach. Judge leads the way, but the Yankees have many homegrown players – Anthony Volpe, Jasson Domínguez, Austin Wells, Ben Rice, Will Warren, Clarke Schmidt, Luis Gil, Oswaldo Cabrera, JC Escarra – who carry themselves with model decorum. They are good, likeable kids, and they are easy to root for. That matters to fans like me, who derive joy from a team’s daily vibe, not solely from its wins and losses.
In particular, there is a direct ‘good guy’ lineage that connects Judge to Jeter to Mattingly and beyond as Yankee captains of exemplary rectitude. Mattingly taught Jeter a lot about what it means to be a Yankee, including one fabled instruction to always run off spring training backfields. Derek, in turn, tutored Judge via the Jeter’s Leaders initiative, and Judge mentors the next generation – adding Spencer Jones and George Lombard Jr. to the current cadre – to create a renewable pipeline of standard-bearers.
Collectively, indeed, these Yankees have reached a point, like all championship teams, where the sum is greater than their individual parts, elevated by ambiguous intangibles. Looking back at the Yanks’ last great dynasty, straddling the new millennium, we see a cast of imperfect players who excelled amid a perfect collective chemistry. On paper, Mark McGwire was better than Tino Martinez, Jeff Kent was better than Chuck Knoblauch, Ken Griffey Jr. was better than Paul O’Neill, Chipper Jones was better than Scott Brosius, and Curt Schilling was better than Andy Pettitte. But not to those Yankees. Not in that time and place. Not in that jigsaw puzzle. And a similar alchemy is taking shape with this current group.
If, in theory, San Diego listened to offers for Fernando Tatís Jr., I’m not sure the Yankees would even get involved. Why? Because Volpe is so embedded in this project – culturally and atmospherically – as to be more important to them than any external import. The same applies to a hypothetical scenario where Boston grows tired of Rafael Devers’ selfishness and puts him on the trade block. Undoubtedly, Devers is a potent offensive weapon, but the Yankee doctrine would probably prefer the comparatively anaemic Oswald Peraza at third base. Why? Because institutional knowledge, forged through shared trauma and channelled into parochial focus, trumps self-centred drama in their model. You can debate the virtues and logic of such a philosophy, but it undoubtedly colours the Yankee outlook.
Aaron Boone, cultural conduit
Aaron Boone, the oft-beleaguered manager, is essential in enabling that selfless, utilitarian culture. Now in his eighth season as Yankee skipper, Boone looks more comfortable than ever in the dugout. I, like many Yankee fans, have voiced frustration with Boone, whose approach to big games can often confound. But overall, he is an affable guy who deserves to win. Boone has spent over 40 years in baseball clubhouses without earning a World Series ring, and I’m rooting for the guy, because he has more than paid his dues.
Boone is regularly dismissed as an inanimate front office puppet with zero autonomy, but he is actually an adept enabler. The ultimate players’ manager, Boone entrusts the veterans on his team to uphold the rigorous Yankee standards. And those veterans are picked using increasingly discerning criterion. “There are ballplayers, and there are Yankees,” George Steinbrenner once said. And though his son has a different interpretation of that edict, he kinda believes in it, too – in his own understated way.
The Yankees of Hal, Cashman and Boone prize quality veterans with an austere visage, evidenced by Paul Goldschmidt, DJ LeMahieu, Cody Bellinger and Trent Grisham. Scouting is heavily involved in such acquisitions, and embodying the Yankee Way is a key consideration. Overall, there is a Yankee template now, outlining what they expect in all facets – broadly generalised as a quiet, dignified, reserved excellence. If you do not meet those exacting standards – as a player, coach, analyst or entry-level employee – you will not be long for the Bronx.
Again, cynics should look at the Red Sox in comparison here. Right now, Boston is attempting to integrate a fresh crop of prospects into its core – Marcelo Mayer joining Kristian Campbell, Brayan Bello, Triston Casas and Carlos Narváez in the next ‘wave.’ Roman Anthony will join them soon. And while certainly exciting, such an influx of talent has not improved the Red Sox’ fortunes. They are still below .500, nine-and-a-half games adrift of the Yankees, because there is no established framework supporting those emerging youngsters. There is no defined culture self-policed by winning veterans – an injured Alex Bregman aside. Boston is even playing its brightest prospects out of position in several cases, speaking to a dysfunctional matriculation pathway ran by naïve and inexperienced operators.
2025 outlook
All of which brings us to the present moment, and a Yankee team that looks formidable. Powered by the extraterrestrial Judge, the two-headed monster of Rodón and Fried, and the resurgent Goldschmidt, the Bronx Bombers are purring. A 39-24 record has them top of the American League East, four-and-a-half games ahead of Toronto and running away.
The Yankees currently lead MLB in homers, OBP, SLG, OPS and wRC+. They rank seventh in team defensive WAR, eleventh in starting pitcher ERA, and fourth in reliever K/9. Every way your dice it, in all facets of the game, the Yankees are performing well, culminating in a 98.2% probability of making the playoffs, per Fangraphs.
When Soto defected to the Mets on 8 December, and when Gerrit Cole saw his season end on 10 March due to Tommy John surgery, such odds seemed fanciful. But after pivoting to add Fried, Bellinger, Goldschmidt and Williams, the 2025 Yankees look more well-rounded than their pennant-winning forebears. I broached that possibility last winter while rationalising Soto’s exit, and much of my best-case scenario has come to pass.
Reinforcements are on the way, too. And while sports fans hate it when teams use the return of injured players as a proxy for trade deadline improvements, it may be true for this Yankee team. As I look at the roster, each glaring deficiency will soon be filled by a returning incumbent. Gil will give them an electric arm worthy of starting a playoff game. Giancarlo Stanton will provide some much-needed righty thump. Marcus Stroman will provide rotation depth through September. And the recent returns of Jazz Chisholm and LeMahieu have redressed an infield chasm.
New injuries will undoubtedly emerge, and every contender could use another flame-throwing reliever, but for the first time in eons, the Yankees do not need a whole lot at the forthcoming trade deadline to augment a championship-calibre team. A power lefty who can deal with Freddie Freeman and Shohei Ohtani would be delightful. But overall, the roster is rounding into shape and peaking at the optimal time, as if last year’s lessons have been learned. That is a testament to the processes which give the Yankees a chance to win each year.
Of course, this is baseball, Suzyn. Anything can happen. We are a Judge hamstring twinge away from doom and depression, and this optimism will count for nought if the Yankees come up short in October. Until they win it all, and finally get over that hump, doubts will rightly linger. The Dodgers will linger, more pertinently, as the only franchise with a comparable claim to destiny.
Fully operational death star
Ultimately, my faith has been restored. Over the years, it has felt cathartic and expedient to make populist kneejerk denunciations amid adversity – fire everyone, abandon analytics, summon the ghost of George – but, in the long haul, such impulsivity is not an efficient way of running a large organisation. Consistency of process does not guarantee optimal outcomes, but it is a more reliable rubric for sustained success than reactionary oscillation governed by raw emotion.
“We’re a fully operational death star,” Cashman once said of his organisation, and I’m more willing to trust him, and it, than ever before. (4) By all means, call me a naïve sheep or a management shill. I’m unperturbed by such criticisms. Yes, I’m leaving myself open to exploitation and heartbreak, but I have noticed a discernible shift in the organisation approach, and my fandom is a whole lot more enjoyable as a result. I’m happier, freed from the stress of perpetual indignation. And while future decisions will undoubtedly irk me, and frustration is bound to arise, I’m on the same page as these guys, straining for the same goal, and I believe in their approach.
It has taken me a long time to mature into such a positive Yankee worldview, and I have had to dilute some of my fundamental sensibilities. Take, for instance, the Starr Insurance sponsorship patches, which besmirch the fabled pinstripes. When that deal was announced, I spiralled into a week-long funk, considering it a blasphemous cash grab. Throughout sports, however, the march of such commercialism is inexorable, and my yelling at a cloud will change nothing and only result in personal agita.
In baseball, more than in any other sport, you need to zoom out and appreciate the bigger picture. Only at the scale of months and years can you separate genuine trends from ephemeral fads. There is a reason we play 162 games per season, after all. You must keep your powder dry, maintain an even keel, and evaluate performance at sensible junctures. That is why the Yankees’ recent series loss at Dodger Stadium did not panic me too much, nor did short-term injuries to Weaver and Volpe. It is all about peaking in October, and the Yankees are well placed to do that.
And so, I will be rooting hard for them, as ever. With each passing year, and each passing heartache, the shared yearning gets more personal, the mutual hunger more binding. This organisation deserves a world championship, which would verify the under-appreciated excellence of its operation. Of course, the Yankees will never receive plaudits and platitudes because, well, they’re the Yankees. But few teams are better run, and a ring would authenticate that distinction.
Sources
1. Kirschner, Chris. The Athletic. [Online] November 8, 2023. https://www.nytimes.com/athletic/5042054/2023/11/07/yankees-gm-brian-cashman-rant-analytics/.
2. Martino, Andy. The Yankee Way: The Untold Inside Story of the Brian Cashman Era. 2024.
3. Witz, Billy. New York Times. [Online] July 25, 2016. https://www.nytimes.com/2016/07/25/sports/baseball/michael-fishman-solving-the-yankee-equation.html.
4. Hoch, Bryan. MLB.com. [Online] December 13, 2018. https://www.mlb.com/news/brian-cashman-refers-to-yankees-as-death-star-c301800628.