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Life lessons from Brian Cashman: How to succeed in the Bronx while really trying

Brian Cashman has now been the Yankees' general manager for 20 years. Adam Hunger/Getty Images

The books in Brian Cashman’s Yankee Stadium office are arranged neatly in two groups, a collection amalgamated over his time as the team’s general manager. Cashman has been in charge for 20 years now, with Saturday representing the anniversary of the day the Yankees announced his hiring.

“Twenty years, in New York,” a rival general manager mused earlier this week. “That’s, what, 140 dog years? Two hundred years?”

During Cashman’s two decades as GM, the New York Knicks have had nine GMs (or someone of equivalent power). The famously stable New York Giants have had three, as have the New York Rangers. In Queens, Mets GM Sandy Alderson followed John Ricco, who served as an interim after Omar Minaya, who followed Jim Duquette, who followed Steve Phillips. In New York, the pressure to win is unrelenting; the scrutiny never ends. And Cashman was hired by George Steinbrenner, who crossed over from sports into popular culture largely because of his habit of firing his employees. So it makes no sense that Cashman has lasted this long.

Anyway, back to his books. The volumes aligned in a row have earned a permanent place in his collection, and those piled on their sides are those he intends to get to someday, between the daily phone calls, meetings and games. Most of them are related to sports -- he likes biographies, like "Lombardi," and anything about the 49ers architect Bill Walsh. But some are self-help books, which Cashman has been drawn to since he was a teenager. Long before Donald Trump’s name appeared on any ballot, Cashman read "The Art of the Deal" and Mark McCormack’s "What They Don’t Teach You at Harvard Business School," as he recalled during an extended podcast interview.

After two decades on the job, Cashman could probably write a self-help book of his own. Some suggested titles follow.

How to Stand Up to Your Boss: The tenure of a lot of Steinbrenner’s general managers before Cashman (and managers, for that matter) could be better measured in days or months, rather than years. Many had extensive track records before Steinbrenner hired them and were quickly worn down, unaccustomed to his relentless demands and chiding. On the other hand, Cashman’s professional baseball resume started with the Yankees, and Steinbrenner was the only style of boss he knew, from his first day as a minimum-wage employee.

Cashman came to realize that you could not possibly survive by simply appeasing Steinbrenner; you had to stand up to him, because if you recoiled and cowered, you’d be useless. He really needed Cashman to stand up to him, and ultimately, he wanted Cashman to stand up to him, to fight for his choices. So there were loud and profane arguments -- many of them -- and Cashman would sometimes push back, responding to a directive with a challenge of his own: OK, I’ll make the deal you’re telling me to make -- and I’ll tell the press that it was your idea. And Steinbrenner would back down, believing that Cashman’s recommendations -- like those of his predecessor, Gene Michael -- had integrity, because he aimed for what was best for the Yankees.

In one of Steinbrenner's last years running the Yankees, the relationship between Cashman and the owner was in a rough patch, as his contract was set to expire. It appeared Cashman might leave, and as he prepared to depart, he gave Steinbrenner what might have been his final recommendation: In order to remain competitive with teams that had become more progressive, the Yankees had to focus on building a sustainable farm system.

Steinbrenner called him back and asked him to stay on, to implement the changes he thought needed to be made.

Making the Right Choices in Business: Rival executives have remarked that Cashman may have steered the Yankees through a turning point in the organization’s history in the summer of 2016, when he recommended to Hal Steinbrenner to execute a strategic sell-off, which ran counter to longstanding club tradition. The Yankees had only rarely been sellers in the trade market; they had always been buyers -- the team that spent the most to get the biggest names. It’s a trait that had often worked and been marketable. But in those critical weeks of June and July 2016, Cashman argued that by moving relievers Aroldis Chapman and Andrew Miller, the Yankees would stock an already improved farm system and then be fully armed moving into the future. They would have financial flexibility as the big contracts of Mark Teixeira, Alex Rodriguez and CC Sabathia fell off the books; they’d have a steady source of good (and cheap) talent; and like the more progressive-thinking teams, they’d get younger.

Hal Steinbrenner signed off on the deals, the Yankees landed Gleyber Torres and Clint Frazier, among others, and now they appear to have a dynamic core of homegrown young players, including Aaron Judge and Luis Severino. They have moved from being mere consumers to being developers.

“The part that they really don’t get enough credit for is how they’ve drafted,” said one executive. “It’s not like they’ve been picking at the top of the draft, but they have really done a great job with that over the last five or six years.”

How to Make the Toughest Decisions: As Cashman said in the podcast interview, George Steinbrenner impressed on him the need to assume responsibility of leadership -- you make difficult choices, and moving forward you take ownership of them. Cashman hired Joe Girardi to be the Yankees’ manager before the 2008 season, and the team won a championship in 2009. But by the end of the 2017 season, Cashman thought that the Yankees needed a new manager, and so he let go of Girardi -- and he answered for the decision with reporters, explaining that he thought there needed to be a better connection between the manager and the players.

It was a stark contrast from the Mets’ after-midnight firing of Willie Randolph in 2008, executed as if the Mets hoped that nobody would notice.

Consensus Is for Wimps: When Joe Torre managed the Yankees, Cashman was known within the organization as the manager’s greatest ally. He carefully attended to Torre, often catered to what Torre wanted and deflected or absorbed the inevitable Steinbrenner anger aimed at the decision-maker in the dugout. After Torre departed, however, he criticized Cashman in his book "The Yankee Years." This seemed to be a turning point for the general manager, hardening his growing belief that a distinct chain of command was needed, with everyone from the manager to the scouts providing insight and information that would inform a hard recommendation for action that Cashman would develop and provide for the Steinbrenner family.

Some of the Best Business Ideas Are Borrowed: The Yankees’ preeminence in the American League East faded after Theo Epstein took over as general manager of the Red Sox. The Yankees survived a seven-game AL Championship Series with Boston in 2003 before suffering an epic collapse in 2004, and what Cashman noticed was that some of the players the Red Sox had acquired seemed to outperform expectations. And he assumed that the Boston front office’s use of analytics and Bill James’ data had a lot to do with it.

So Cashman built his own analytics team, and through the years he has continued to draw upon information and ideas gleaned from other organizations, from the San Antonio Spurs to European soccer clubs, in the same way that he pulled thoughts and inspiration from those books on his office shelf.

Among baseball operations honchos, only Brian Sabean of the Giants and Oakland’s Billy Beane have served longer than Cashman, but Cashman’s is the most unlikely path: New York, the Yankees, George Steinbrenner. And yet ... 20 years. Explaining that would probably require volumes.