IN THE LINE OF FIRE
DESPITE FAN CRITICISM AT A FEVER PITCH, GM BRIAN CASHMAN RUNS THE YANKEES THE ONLY WAY HE KNOWS HOW AFTER A QUARTER-CENTURY ON THE JOB: WITH BLUNTNESS, HUMOR AND CONVICTION
THE MOST powerful person within the most powerful baseball team on earth is a thin, bald, bespectacled, 5-foot-7 man who grew up on a horse farm in Kentucky. Hollywood turned to Brad Pitt to portray longtime A’s executive Billy Beane. Jason Alexander (who has a Yankees connection anyway) might be the better match for Brian Cashman.
In an era in which the faces of baseball teams’ operations departments are Ivy League-educated, formal and highly skilled at saying little — with lexicons that are heavy on sustainability and predictive modeling — Cashman played baseball at Catholic University, graduated and essentially earned his masters at George Steinbrenner University. If you can make it there, you can make it anywhere.
The voice of the Yankees speaks like, well, a human. Cashman labeled the 2023 Yankees season a “disaster.” Months later, amid an endless barrage of arrows slung against him and anyone in pinstripes, Cashman said the Yankees’ processes “are pretty f--king good.” And no, he does not have any regrets about that news conference and his fiery defense of the organization.
There are a few who arguably could come close, but Cashman does not have a peer. He is the longest-tenured lead decisionmaker in MLB by about a decade and the longest in Yankees history. (Cashman started in ’98, John Mozeliak with the Cardinals in November 2007.)
In New York, the turnover is relentless. The Mets have had six lead executives since 2018. The Knicks churned through Phil Jackson, Steve Mills and Scott Perry before perhaps finding some staying power in Leon Rose.
In sports, the turnover is relentless. The pillar of football stability, Bill Belichick, is gone after 24 seasons in New England. The only NFL lead execs who have been in their roles longer than Cashman are Jerry Jones (Cowboys) and Mike Brown (Bengals) — and both require asterisks because they own their teams.
In a sport and a city that eats executives alive, Cashman has proven to be an unprecedented constant. He was the one person George (and now Hal) Steinbrenner could not fire. His legacy is a fascinating and perhaps evolving one, helping to construct a dynasty from 1996-2000 but only winning one World Series (2009) since. Whenever his run is over, will Cashman be better known for the titles or for his inimitable durability, consistently dodging every bullet fired by a proudly spoiled fan base and the back pages that question his every move?
In virtually every way, Cashman is different from those who came before and those who remain. Friends and rivals, more than a dozen interviewed for this story, point at a rare honesty, a unique ability to connect and a particular ability to laugh, along with a willingness to adapt as the qualities that have enabled him to become the ultimate baseball survivor.
“Being able to be steady under that level of pressure and that level of expectations with that amount of success over that period of time is a virtual impossibility,” said current agent and former Mets GM Brodie Van Wagenen. “He’s done it in a way that few people can understand.”
Let’s try to understand as Cashman
embarks on his 27th and perhaps most important season as Yankees GM, the only job he has ever wanted.
THE ORIGINS of the relative nobody turned boss (lowercase b) is a legend that has mostly been told. Cashman is a Yankees lifer, joining the organization as a college intern in 1986 in large part because his father became friendly with George Steinbrenner through horse racing.
Cashman graduated college in 1989 and became a full-time assistant in baseball operations. He soon was transferred to Tampa, where the real brain trust of the organization resided.
“He went from the mailroom to the boardroom basically,” said Jean Afterman, a senior vice president and assistant general manager who negotiated against Cashman as a player agent until he hired her.
Cashman was promoted to assistant farm director in 1990 and learned from scouting “giants,” as team president Randy Levine called them, such as Gene “Stick” Michael, Bill Livesey, Mark Newman and Brian Sabean, who then was the vice president of player development/scouting.
“We knew that the family, more so his dad, had a relationship with Mr. Steinbrenner. And within that context, we saw that this guy just wasn’t passing the time,” Sabean said. “He really was interested in learning the business and maybe staying in the business. … He could have been viewed as a political appointment, but once you get to know him, you saw he was the furthest thing from that.”
A kid born in Rockville Centre, raised by baseball and horses and eventually George Steinbrenner, became general manager in ’98. His unique upbringing — not a former pro but a player who got to know the game and its personnel through high school and college games; who learned to hang out with the scouts, with George, with manager and later broadcaster Billy Martin, with Don Mattingly and Dave Winfield — afforded him a unique ability to “play in so many different types of sandboxes,” as longtime vice president of communications and media relations Jason Zillo put it.
“Getting exposed to people from different walks of life, different perspectives, different cultures, different political views, all that stuff,” Cashman said, “I’m sure all that gets baked into forming my personality, whatever it happens to be.”
Cashman has survived because “he’s won,” Levine said. He is right, but only to a degree. Each of Cashman’s first three seasons brought
a World Series title. Among GMs with at least 10 years of experience since 1950, his lifetime winning percentage of .585 (2,404-1,702-2) is the best. He has the advantages of the Steinbrenner wallet, but 26 straight seasons without a losing record is unfathomable nonetheless.
The less-tangible reasons explain why he has survived when the wins — at least in the final game of the season — have dried up.
ACCORDING to many around him, Cashman is direct — with his employees, with his bosses, with opposing executives and with agents.
He can manage up, essentially another Steinbrenner child who learned how to absorb George’s explosions. He can manage down, earning high marks among his own employees and showing a frank honesty in dealing with the press.
“He just has an innate skill that can’t be taught of how to be able to read a room,” Zillo said, “whether it’s top-level sponsors or top-level executives or in the coffee room with a bunch of interns. He’s got a great dexterity in the way that he communicates.”
There is no doublespeak or hidden meanings, no hints or oblique text messages when a simple call or face-to-face conversation can settle a matter.
In identifying players he wants and the prices he wants to pay, Cashman is straight-forward. “We’ve never really played games in communication,” said Van Wagenen, who has faced off with Cashman in free-agent negotiations [most recently in repping Marcus Stroman] and when he was Mets GM. “That’s unique in the game, whether it’s agents, whether it’s front-office officials. There’s usually a game of chess that takes place in some of the communication. “But for Cash, here’s what he wanted. He was honest.” Seth Levinson, a noted longtime agent who has repped Yankees from Jorge Posada to Clint Frazier and who has known Cashman since he was an intern, said Cashman is the rare GM who will simply hammer out details over the phone rather than engage in a lengthy text conversation. Texting allows a poker face, a means toward hiding true feelings to avoid the risk of losing leverage. Cashman doesn’t need one. “He is candid, transparent, honest and consistent, and his adversary will always know where he stands,” said Levinson, who has battled with Cashman for decades and who trades insults with the GM that amount to terms of endearment between the old and good friends. “Plus, his word is golden, and he’ll stand by it regardless of the circumstances.” “Brian will always call you back,” said Beane, a longtime rival and friend of Cashman’s as the Moneyball A’s executive. There is a directness to Cashman’s manner but also an honesty. Several executives under Cashman said he has told them to never lie or cover for him. For all the criticism that fans launch at Cashman, a lack of accountability is not among them.
He does not paint the same rosy picture many executives paint when speaking to reporters. This offseason he had to relive and re-apologize for one comment, talking with Van Wagenen and Stroman to ensure an unflattering remark he made in 2019 about the righty was forgiven. And he had to talk with Giancarlo Stanton after saying at the GM meetings that the oft-injured outfielder is “going to wind up getting hurt again more likely than not because it seems to be part of his game.”
“Some of them you look back and regret,” Cashman acknowledged, speaking in general terms about his instinct to speak candidly. “Sometimes it’s better to be brutally honest. And whether I say, ‘We suck right now,’ when the press says, ‘What do you think about your team?’ … Sometimes I’m public with acknowledging what our fans have been watching. Like, ‘It’s not watchable right now, and you’re right, and we’re frustrated, just like you’re frustrated.’ ”
According to Cashman and many around him, his bluntness is not a tactical move but just who he is. He speaks off the cuff because it is how he has always spoken and, “It’s too much work to try to recreate a world that doesn’t exist,” he said.
So the explosion at the GM meetings was not planned, even if it did serve a purpose.
AFTER his first playoff-less season since 2016, Cashman heard every complaint. Injury and underperformance occurred all over the roster, and he was bothered that media and fans had targeted the Yankees’ reliance upon advanced analytics, rosterconstruction issues and, generally, that “we don’t know what we’re doing,” he said.
Anger built up until it was unleashed on Nov. 7 in Scottsdale, Ariz., where Cashman issued fullthroated defenses of the Yankees for about 67 minutes. Their way of operating is “pretty f--king good,” he said; he wanted to separate fact from “bulls--t,” believing critics pouncing upon a weak season were bringing hammers when chisels could be used.
According to Cashman and everyone around him, what might have looked like a performance was not a performance.
“I’m very protective of our people and our process,” said Cashman, who added he heard from some that it was “awesome” and from some he could clean up the cursing. “We have a good process, and as I said, we have good people.”
Even if it wasn’t a performance, that does not mean it didn’t have an audience.
“I appreciated [the defense] because there’s the understand
“PEOPLE SHOULD REALIZE HE’S THE REASON THE BAR IS SO HIGH.” — A’s senior adviser Billy Beane on Brian Cashman
ing he sees the work that really everybody in the baseball operations department is doing and all the good things that are going on,” said Michael Fishman, an assistant general manager and essentially the head of the Yankees’ analytics department. “Everything we’ve been developing internally — he has an inside knowledge of the core operation that the public doesn’t have, so he has maybe a different perspective that he can speak from.”
Apart from Cashman, Fishman might be the largest target in the organization. Cashman began catching up to the Moneyball wave by hiring the then-analyst in midseason 2005. The Yale graduate with a bachelor’s degree in math quickly earned the ear of Cashman — part of conversations that led to the trade for Shawn Chacon and call-up of Aaron Small, which helped save that season — and became a oneman department that Cashman embraced. About a year later Fishman was promoted, from analyst to director of quantitative analysis, and he could start building up what today is one of the biggest analytic staffs in baseball.
The staff is constantly under fire by fans of a game that is steeped in tradition and not projection. When things go wrong — as they did during the 2023 collapse — the analysts are often the shadowy faces blamed. Cashman is, too, as the one who empowers them.
Ahead of this season, the Yankees have brought in an analytic firm to review their own analytic process, Cashman trying to see if he and the department need to adapt. His people, he will insist, are not a problem.
“He always takes responsibility — where he feels it’s warranted,” Afterman said after watching Cashman’s outburst in Arizona. “But he’s also somebody that will call out bulls--t. I think that was calling out bulls--t.”
It was a display of frustration following a season of frustration. As far as outbursts go, Cashman prefers laughing.
ASIGNIFICANT factor in Cashman dealing well with people above and below him is his not being above any middle-school prank he can pull.
Cashman has played with a fart machine for years, planting it in rooms around the Stadium and watching from afar as people within try to decipher who is the one passing gas.
“I actually picked it up from him. I’m using it now,” said senior adviser Omar Minaya, whose humor pairs well with Cashman’s.
Another favorite of Cashman’s: fake lottery tickets. Cashman is known for giving out authenticlooking scratch-offs and watching as his victims “win” hundreds or thousands of dollars.
“There are a lot of innocent people who don’t know Cash like I do,” Zillo said, laughing. “[They would think], ‘This can’t be fake because Cashman gave it to me.’ ”
“There’s so much stress and pressure around us at all times — not just in this industry, in any industry or walk of life,” Cashman said. “I just think that when you’re operating in a fishbowl, no matter where it happens to be, it certainly makes life easier if you can bring fun to the party.”
In a job that multiple agents and executives called the hardest in all of sports, Cashman does not take himself too seriously. He comes across as authentic rather than calculated.
“I don’t think he writes his jokes beforehand like Sandy Alderson does,” Van Wagenen said.
POSE the question to anyone around the Yankees and the answer is roughly the same. No, this make-or-break year for the Yankees does not feel different. They know they only have one year guaranteed of Juan Soto, for whom they mortgaged part of their pitching future. They know their core is a year older, with several ominous contracts on the books.
But they also know that every year is a make-or-break season for the Yankees. This is not unique.
The only one to acknowledge a growing urgency was Hal Steinbrenner.
“There’s more pressure on all of us,” Steinbrenner said when asked if there is more pressure on Cashman this year. “Look at me. I mean, look at the bags under my eyes. There’s pressure on all of us, man. We’re feeling it and that’s a good thing. We deserve to feel it.”
Cashman has not won since 2009. He is coming off a season that featured devastating injuries (Aaron Judge), questionable signings (Carlos Rodon) and no October baseball.
The Yankees were 71-72 on Sept. 10 before rallying to finish two games over .500, preserving one of the more impressive streaks in baseball: Cashman has never had a losing season. Privately, a Yankees executive praised Cashman and manager Aaron Boone for finding a way to navigate to mediocrity in a season that seemed destined for worse.
Beane watched from afar and learned that the Yankees had not sunk under .500 so late in a season since 1995 — since before Cashman took over. Beane laughed. What fans use as an indictment, Beane believes should have been an acquittal.
“That actually epitomizes it — people should realize he’s the reason the bar is so high,” Beane said about the 26 straight winning seasons. “To me, that basically says it all right there.”
Cashman understands the market and is accustomed to dealing with angry fans, sometimes personally.
Back around 2000 (the year and date blurry), Cashman watched Roger Clemens start a heated Subway Series game at Shea Stadium. Cashman left his seat to navigate through the crowd and get to the Yankees clubhouse when three seemingly drunken Mets fans approached, berating and cursing him, a fight close to breaking out. Cashman “started losing my temper,” he remembers, and shouted back at a group that was maybe a foot away.
Levinson, an agent who is ostensibly his adversary, happened to be attending the game and witnessed the developing scene. He grabbed his son, who might have been 5 at the time, and joined Cashman’s side.
“I said, ‘If you are going to do this, then let’s even the fight up,’ ” Levinson remembers.
In Levinson’s recollection, the three guys saw his son, realized the stupidity and walked away. Cashman remembers Levinson arriving “when it was getting ugly” and helping the incident die down before a punch was thrown.
How does Cashman survive? It helps that even the people who are supposed to oppose him will fight for him.