Big Picture: 'Hall of Famer' Brian Cashman Changes With the Times, Blocks Out Noise

George M. Steinbrenner Field (Tampa) – Brian Cashman walked into his office at the spring training facility for the New York Yankees and pulled up a TikTok video on his iPad. He had already seen this video but thought it was funny enough to watch it again.

The team's general manager laughed as the clip showed two men arguing with each other, before one of them threw his Big Gulp cup at a car. The liquid from the cup smothered the car windows, the men continued yelling, and the video ended.

Watching inherently silly TikTok videos is "a nice diversion from the noise," Cashman told me when we sat down in his office to discuss what it’s like being the longest-tenured GM in Major League Baseball. 

When he’s not scrolling, he’s busy building a championship-caliber roster, modernizing the organization with wide-ranging changes, and fine-tuning his baseball operations department.

The noise, in this case, is a relentless stream of criticism and title expectations. Cashman, too, said he has a ticking clock in his head, reminding him that the Yankees haven’t won a championship since 2009. Due to that drought, criticism of Cashman has become as predictable as October in the Bronx. Every roster decision by the Yankees GM is dissected. Every postseason exit is used as evidence that the architect of baseball’s most successful and scrutinized franchise has lost his touch.

Brian Cashman and Aaron Judge, two of the most talked about figures in New York. (Photo by New York Yankees/Getty Images)

Debate around Cashman has played out forcefully in New York. He’s anatomized on talk radio, across social media, and in the stands at Yankee Stadium. The argument is familiar: the Yankees should win more and spend more, and they should think differently. Cashman hears it all, even when he’s no longer trying to, even if he barely responds anymore. What the public sees, though, is only part of the story.

"I'm pretty simple," Cashman said. "The reason we're able to adjust and change is because I am very open-minded, and I challenge our staff to be the same way. If someone's doing something better than we are, we have to figure that out as fast as we possibly can, and then adapt and adjust and grow because of it."

Inside the organization’s walls and across major-league front offices, Cashman is revered as a brilliant executive who has survived multiple baseball eras and worked under two different ownership styles with aplomb.

"It is next to impossible to have the longevity he's had for any team," Mets president of baseball operations David Stearns said. "To do it in New York makes it kind of unthinkable in this day and age. I think it speaks to his talent. I think it speaks to his leadership capabilities. It has to speak to his ability to compartmentalize and focus on what is important to do his job, and he's done it incredibly successfully. Whenever he decides he's had enough, we'll all be celebrating in Cooperstown shortly thereafter."

Cashman started as a Yankees intern in 1986 in the minor-league scouting department. After he graduated from college, the team offered him a full-time job as a baseball operations assistant. Back then, analytics departments were tiny, sports science barely existed, and the game’s most famous franchise operated largely on instinct and tradition. Cashman took over as general manager in 1998 and has overseen four World Series titles and 23 postseason appearances.

The Yankees won the first of three straight World Series in Brian Cashman's first season as general manager. (Chuck Solomon/Sports Illustrated via Getty Images)

Since then, the Yankees have produced a winning record for 33 consecutive seasons, second longest in MLB history behind the team's 39-season streak from 1926-1964. Cashman believes everything from the aesthetics of the Yankees clubhouse to the recent renovations inside the spring training facilities to the tireless work of his staff has played a significant part in making the organization a well-oiled winning machine. Plus, he’s constantly drawing inspiration from other marquee sport franchises.

​"It's not like I can intimately get behind the scenes of the Cincinnati Reds and see what they're doing," Cashman said. "But I can do that with the University of Kentucky. I can do that with the New York Giants or the Brooklyn Nets or Alabama football or, the New Zealand All Blacks or Manchester City or Arsenal or what have you. We can do that with a lot of different other environments or even businesses that aren't sports related, and we try to engage and find out what drives their culture.

"How do they manage their processes and why? And if they're successful, why? Is it just because they have great leadership? Is it because they got lucky? Is it because they rely on certain core principles?"

Key To Success: Constant Change

Twenty or thirty years ago, Cashman struck up a conversation with a bartender at a Ritz-Carlton during a Yankees road trip and learned about their official Code of Conduct, a sheet of paper that every employee had to carry in their pocket at all times. It outlined ethical and behavioral guidelines for all employees of the luxury hotel brand, including management. Cashman doesn’t remember if he took a picture of the sheet or the bartender gave him a copy of one, but he took it home to study it. He found ways to embody those guidelines as a part of his own leadership styles.

Through the years, Cashman has developed relationships with various sports executives, everyone from the Tampa Bay Lightning general manager Julien Brisebois to the Philadelphia Eagles GM Howie Roseman. They send each other articles on leadership and exchange ideas on how to improve. Cashman is still curious about outside ideas and finds ways to incorporate them into his baseball operations. Sometimes, that inspiration arrives in unusual ways.

Recently, he went down an escalator at the newly renovated LaGuardia Airport and snapped photos of a design he liked. He shared it with his staff and Yankee Stadium operations, and they worked to incorporate the design into the ballpark.

"Brian has tried to keep the Yankees more relevant and more current and modern," former Yankees manager Buck Showalter told me. "And, all the while, he doesn’t take himself too seriously. I got a lot of respect for him, he started on the ground level and worked his way up."

Cashman learned from Showalter that altering the atmosphere in little and big ways prevents the environment from becoming stale. He believes part of the reason the Yankees went to the World Series in 2024 is because of the renovations he helped initiate at their Tampa facility that year.

Cashman said that those multimillion-dollar upgrades, including a health and wellness center, extended batting cages, and a player lounge, compelled players to spend more time at the ballpark. His incessant hunt for fresh changes and ideas are all designed to help the on-field product produce more wins and have fun doing it. Netflix recently shared its company values with the public, and Cashman absorbed it like a sponge.

"Constantly trying to change and remake yourself is important," Cashman said. "I just want to find out what's underneath the hood and what makes somebody or some company or some sports entity tick. And if they're having success, there are reasons behind it."

Micro-Manager? 'I'm The Opposite'

The public perception is that Cashman is stubborn. The fanbase’s disapproval of him reached an all-time intensity after the 2023 season, when the Yankees missed the playoffs and came under fire for their analytical approach. Cashman was on way to the annual GM Meetings that offseason when Yankees media relations tried to warn him about the brutal line of questioning headed his way. The heat was going to be turned all the way up, but Cashman wasn’t interested in mincing his words.

In a lengthy scrum with the media, Cashman defended his front office in a curse-laden rebuttal of the perception that the Yankees should clean house because their baseball ops had become ineffective. The GM, criticized for protecting manager Aaron Boone and the rest of his coaches, analytics and player development staff, believes the negative public perception and the internal success of his baseball ops is worlds apart. The following season, the Yankees went to the World Series. He doesn’t regret a single word he said in that infamous scrum.

"I'm definitely not a micro-manager," Cashman told me. "I'm the opposite. I am someone that will hire people I consider smarter than me and that have expertise in that area. And then I empower you to do your job. I will support you every step of the way, including in that scrum, defending you to the hilt, because you still might not be on top. But if you've done everything you possibly could do, and you're really good at what you do, then I'm gonna have your back no matter what."

Part of the reason that eruption from Cashman went viral was because he doesn’t say much these days. He also doesn’t read or listen to what people are saying about him. He doesn’t have social media on his phone anymore, besides TikTok. It’s a complete reversal of how he used to start his days, by returning calls from reporters and appearing on the field pregame to answer any questions and divulge his processes. In recent years, the GM has learned that explaining decisions rarely quiets criticism. It only fuels it.

"The media coverage is completely different," Cashman said. "To the point where now, I'm very reclusive."

While the debate about the Yankees’ direction continues outside, Cashman has increasingly stepped back from the conversation, focusing instead on the work inside the organization he has spent nearly three decades shaping. That’s not to say he’s at peace with the fan base’s perception of him. He knows a large segment of Yankees fans are frustrated that Cashman is running back the same roster this year as the one they ended with last season.

"Stuff like that bothers me," he said. After all, last year’s team tied the Toronto Blue Jays for the best record in the American League East before it lost to the Blue Jays in the AL Division Series. Plus, ace Gerrit Cole will return from injury this year. So it won’t be the same team as last season, he said. People are getting that wrong.

Why, then, doesn’t he speak up more?

"I've learned over the course of time, it doesn't matter what you say," Cashman said. "What do you do? I can try to fight like Don Quixote with the windmills out there and all those battles all the time. But is that a really efficient use of my time?

"Like at the end of the day, I know all that's going to matter is if we're winning games. And even when we are winning games, it still won't matter. Because there's a lot of narratives out there that just aren't the case. Like, to this day, I'm definitely frustrated with the one narrative that the manager is the puppet and we're dictating his moves. None of it's true."

Cashman has tried to refute a long-believed narrative that Boone doesn’t make any decisions, including lineup construction and in-game bullpen management, and that the GM maps out a game plan for the manager ahead of time. For years, he’s seen his comments get pulled apart, misinterpreted and weaponized. Cashman realized it was unhealthy for him to spend time fighting battles against false narratives. So he stopped, for the most part.

"I'd rather people be right," he said. "But I've gotten to a level, too, where it's almost like I accept it. I can't change people's minds. They want to believe what they want to believe no matter what. It's like politics and conspiracy theories. You can try to prove it scientifically, prove it with people testifying under oath or like, I can roll out former managers, you can ask those guys. It doesn't matter. It doesn't mean anything. People still say it. So it's like, well, then what am I going to do?"

Cashman's Legacy? It's Complicated

Boone, sitting in his desk chair in his office at George M. Steinbrenner Field, leaned back and smiled as he recounted day-to-day instances of Cashman being a "practical joker."

One time, Boone was upset about something, and Cashman called the manager’s office phone and disguised his voice. Other times, he’s carried in his pocket some paper snappers, which produce a loud exploding pop when thrown, to mess with people.

"​​He takes something that happens in our day-to-day, something serious, and he'll lean into it and make it humorous," Boone said.

Yankees skipper Aaron Boone alongside team GM Brian Cashman. (Photo by New York Yankees/Getty Images)

"But what I really admire about him is his consistency. He’s funny, but ​​he's willing to have any difficult conversation and hold people to the fire. To do it with the excellence he's done, for as long as he's done it, it's remarkable. It takes a very special talent, evaluator, and vision to have that sustained excellence. Even though we haven’t won, he's putting together a championship-caliber program all the time. I think he’s a Hall of Famer."

There is no job in baseball where success is defined so narrowly as the one Cashman holds with the Yankees. In most cities, consistent playoff appearances would be celebrated. In the Bronx, trips to October are treated as disappointments without, at the very least, a World Series appearance. That dynamic has made Cashman one of the most criticized executives in the sport — and one of the longest tenured.

Cashman’s tenure is defined by a remarkable absence of losing seasons, a high level of sustained success, a lengthy championship drought and a heavy dose of frustration. It’s complicated. He finds it excruciatingly difficult to reflect on his career, particularly because he’s not done. He wants to change the narrative, and he knows the only way to do that is by winning.

"Reggie Jackson was one of the most prolific home run hitters of all time," Cashman said. "But he was also one of the most prolific strikeout leaders of all time. As the game is playing out, he might’ve had three strikeouts his first three at-bats. But he could always change the narrative with one swing.

"So, I’m still swinging."