How Brian Cashman has survived the most volatile job in sports

(Paul Rosales/Yahoo Sports illustration)
(Paul Rosales/Yahoo Sports illustration)

NEW YORK – Back in July 1987, a teenaged member of the New York Yankees support staff happened to be in the room when Woody Woodward received a call from George Steinbrenner.

About two weeks earlier, Woodward, the Yankees general manager, had carried out The Boss’ order to trade Joe Niekro, the 42-year-old knuckleballer who had just finished his second season as a Yankee. And now, as a starter for the Minnesota Twins, Niekro had baffled the Yankees for seven innings. The Yankees wound up winning the game, but the Boss was fuming.

From the speakerphone on Woodward’s desk, the voice of Steinbrenner blared out loud and clear: “Now, Woody, this is what you’re going to do. You’re going to go down to the clubhouse and you’re going to take full responsibility for this move. You’re going to make sure the press knows I had nothing to do with this.”

All Woodward could say was, “Yes, sir. Yes, sir. Yes, sir.”

And the 19-year-old staffer, working a summer job between semesters at Catholic University in Washington, D.C., thought to himself as he listened in, “Man, I would never want that job.”

That 19-year-old’s name was Brian Cashman, and for the past 21 years, “that job” — the job that ate up Clyde King, and eventually Woodward, who succeeded him the following season, and Lou Piniella and Gene Michael and Gabe Paul and Bob Watson and in fact, all 11 men who held it during Steinbrenner’s stormy first 25 years as owner of the Yankees — has belonged to him.

And now it seems like there’s virtually nothing he could do to lose it.

“As long as I’m a general partner of this team,” said Hank Steinbrenner, the older of George Steinbrenner’s two sons, “Brian Cashman will be the general manager.”

That is remarkable considering that when he was hired as a 31-year-old to replace Watson, Cashman was the 12th general manager hired by Steinbrenner, a man who seemed to change GMs as often as he changed his socks.

The Yankees revolving door

Only one of Cashman’s predecessors held the job for as many as seven years, and that was Michael, who required two stints, with a stormy managerial stint in-between. Every other one of George’s GMs lasted one or two seasons at most before either being pushed off the ledge, or jumping first.

Working for Steinbrenner was “a very difficult, demanding job,” says Joe Torre, who endured his own remarkable 12-year run as the Yankees manager. “You always have to live up to being part of the Yankees. It keeps you on edge.”

And yet, Cashman has worked in that pressure cooker for nearly twice as long as Torre. Longer, in fact, than all but one of his 18 predecessors, Ed Barrow, who held the post for 24 years and benefited greatly from having players named Ruth, Gehrig and DiMaggio and an owner not named Steinbrenner.

The recent firing of Dave Dombrowksi by the Boston Red Sox less than a year after the team he built won 108 regular-season games and the World Series, only serves to remind us of how mind-boggling Cashman’s longevity is.

When you add in the fact that the Yankees have not won a World Series in 10 years, an eye blink for most franchises but an eternity for this one, Cashman’s record of steady employment borders on the surreal.

But what may be even more incredible is that, over the past 10 years in which Hal Steinbrenner assumed the reins from his aging dad, Brian Cashman has become the official voice of the Yankees. In his own quiet way, Cashman has relegated the Yankees owner to the background, a situation that would have been unthinkable when George was alive but seems to be exactly the way Hal wants it.

** FILE ** New York Yankees general manager Brian Cashman, left, talks with principal owner George Steinbrenner, before the Yankees spring baseball game against the Boston Red Sox at Legends Field in Tampa, Fla., in this March 22, 2006 file photo. (AP Photo/Kathy Willens)
George Steinbrenner, right, named Brian Cashman, left, as Yankees general manager in 1998. (AP)

The secret to Cashman’s success

Ask Cashman how he has managed to successfully navigate a minefield that chewed up so many of his predecessors and he will tell you, “We’ve had great players and I’ve been fortunate to work with a tremendous staff. And I’ve been blessed to work with the Steinbrenner family for all of my adult life.’’

When told there has to be more to it than that, he says, “You’ll never get that from me. I’m not going to be patting myself on the back and have to go to Dr. Andrews for rotator cuff surgery.”

Instead, leave it to Randy Levine, the Yankees president and probably the man closest in temperament to George Steinbrenner in the organization, including George’s son Hal, to explain the secret of Cashman’s survival: “He’s really smart, he’s adaptable and he knows how to work with people. He’s strong and he holds his ground, but he’s not stubborn. If other people have ideas that are better than his or that he disagrees with, he’s flexible enough to change. And, he’s loyal.”

That last may be the most important trait for working well with the Steinbrenners; Cashman said he has turned down numerous offers, for more money and less agita, over the past 20 years because “I never forgot I am nobody without George touching [my career], without him giving me the opportunity to be an intern, then his assistant farm director, his assistant general manager and eventually taking the chance on making me his general manager. I felt that as long as he wanted me here, there’s no way I could walk away from him. He created me.”

The Yankees have had 22 consecutive winning seasons since Cashman took over in 1998. Including 2019, they have won 100 games or more seven times. They have won four world championships, 13 division titles and missed the playoffs just four times.

Still, Cashman says, “I feel like I’m under pressure every day.”

He does concede, however, that working for Hal is not like working for George.

“Definitely a different management style,” he said. “He would threaten you, tell you you’re on the clock, you better be right or you know what’s going to happen, stuff like that.”

And how many times did he fire you?

“Officially, never. But the threat was always there.’’

Hal Steinbrenner declined to be interviewed for this story, but his brother Hank said, “It’s not like it was before. Things were a lot more tumultuous back in the ‘70s and ‘80s.”

Said another Yankee employee who requested anonymity, “I think it’s gotten a little easier for Cash to work under Hal.”

New York Yankees General Manager Brian Cashman looks out from the dugout at baseball spring training camp, Wednesday, Feb. 21, 2018, in Tampa, Fla. (AP Photo/Lynne Sladky)
Brian Cashman has been GM of the Yankees for 21 years, and is in no danger of losing his job as long as Hal Steinbrenner is in charge. (AP)

Is 2019 Cashman’s masterpiece?

This year, the Yankees won their first American League East division title since 2012, and they did it despite an unprecedented cascade of injuries — they placed a record 36 players on the injured list, including every one of their starters, and lost 2,246 games to injury — and are neck-and-neck with the Houston Astros in the race for the best record in baseball, and the homefield advantage throughout the playoffs that goes with it.

And most nights this season, the Yankees have done it with a lineup that even the Tampa Bay Rays could afford. Instead of $21 million, perpetually injured Jacoby Ellsbury in center, the Yankees have used Brett Gardner for less than half the price. In place of $26 million Giancarlo Stanton, the Yankees have divvied their DH role among Edwin Encarnacion, Clint Frazier, Luke Voit and Mike Ford, who cost about a third of that combined.

The Yankees have gotten world-class production out of the likes of Gio Urshela, who was was in the running for the AL batting crown before, of course, going on the IL with a groin injury at the end of August; from D.J. LeMahieu, a former NL batting champion who the Colorado Rockies allowed to leave in free agency and is currently hitting .328, and Mike Tauchman, who filled in more than admirably when Aaron Judge missed more than two months with an oblique strain.

If nothing else, the 2019 Yankees have proven that Cashman and his staff can beat you with more than Hal Steinbrenner’s checkbook.

Urshela was acquired from the Toronto Blue Jays for $25,000, or about the price of a Hyundai Santa Fe. Tauchman came from the Rockies in a trade for minor-league pitcher Philip Diehl. And the Yankees tied up LeMahieu for two years at $12 million per year, the same amount the Mets paid for another infielder, Jed Lowrie, who except for a handful of pinch-hitting appearances has yet to play a game this season.

Simple rule of thumb: If Cashman wants one of your guys, hold onto him. And if he’s willing to part with one of his, pass.

“That’s something that Brian and his regime have done for years now,” said Billy Eppler, who worked under Cashman as an assistant and is now the GM of the L.A. Angels. “Having seen it first hand, it doesn’t surprise me at all.”

Eppler admiringly calls Cashman’s maneuverings at the 2016 trading deadline, in which he moved his two stud relievers, Andrew Miller and Aroldis Chapman, in exchange for prospects Clint Frazier and Gleyber Torres, “Arbitrage at its finest.”

Not only has Torres exploded offensively — he has 38 home runs as a 22-year-old second-year player — but Cashman was able to re-sign Chapman to a three-year contract after he was done helping end the Chicago Cubs’ 108-year World Series drought as a three-month rental.

And this year, when the Blue Jays were demanding Frazier be included in a deadline deal for Marcus Stroman, Cashman refused to let the promising but erratic young outfielder go.

“We were interested in Stroman but we didn’t think he would be a difference-maker,” he said. “We felt he would be in our bullpen in the postseason.”

Cashman deserves nearly as much credit for the moves he and his staff chose not to make; passing up on Manny Machado and Bryce Harper, for instance. Aside from home runs, Machado’s stats are not as good as Urshela’s and despite adding Harper, the Phillies didn’t qualify for the postseason.

“In certain circumstances we acquired players because we felt they had some untapped potential that we were going to bet on,” Cashman said. “And some guys we just got as insurance policies in case things went wrong, which they did.”

Tauchman and Luke Voit — who has hit 35 home runs in 139 games over parts of two Yankee seasons after the Cardinals gave up on him — were acquired as untapped potential guys. Encarnacion was an insurance policy for Voit, who sure enough, got hurt. Urshela was picked up as an inexpensive backup for Miguel Andujar, who wound up tearing a shoulder labrum 12 games into the season.

“We thought maybe he’d be a utility player for us,” Cashman said of Urshela. “But never did we expect we would be sitting on Manny Machado, you know? But that’s the kind of season we had.”

“Cash has a great sense of which players to sign and for how much,’’ said Levine, with whom Cashman publicly disagreed over the re-signing of Alex Rodriguez in 2007 and the signing of Rafael Soriano in 2011. “I think the signing of LeMahieu was one of the greatest Yankee signings in decades.”

Cashman has not done as well with starting pitching. Sonny Gray was a bust in his two years as a Yankee. This winter, he was unable to come to terms with free agent Patrick Corbin, who wound up having a good season for the Washington Nationals. And the Yankees, among 28 other teams, also passed on their old nemesis Dallas Keuchel, who has won five of his past six starts for the Atlanta Braves.

For a time, it appeared the Yankees’ major offseason pitching acquisition, James Paxton, would turn out to be another Gray, but he has rebounded to be the team’s best starter the past two months, and Luis Severino, out with a shoulder injury for much of the season, returned this week looking as if he could be a major factor in the playoffs.

“Life’s full of regrets,” Cashman said. “But this year, I have no regrets. I feel like we’ve accomplished phase one of our goals, which was winning the division, and we’re in pretty good shape for the next phase. But until we win the World Series we really haven’t accomplished anything yet.”

George Steinbrenner couldn’t have said it better than that, which is hardly surprising since, as Cashman said, “I’m a graduate of Steinbrenner University.”

After 21 years, Cashman is more than just a graduate. Now, he's more like a tenured professor.

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