It was one of the best days that Brian Cashman had growing up. He was in sunny Florida, surrounded by his childhood heroes, and he got to wear a Los Angeles Dodgers uniform.
The photographs from that day in 1982 seem a bit incongruous now, because Mr. Cashman, the general manager of the New York Yankees, has become synonymous with that team, which is trying to beat the Dodgers in the World Series.
But there he is, in full uniform, a mitt on his left hand, standing next to Tommy Lasorda, perhaps the most recognizable person ever to dress in L.A. Dodgers blue.
“I loved the Dodgers growing up,” Mr. Cashman said in a telephone interview last week, “so that day was very special.”
Mr. Cashman’s devotion ran deep, but several years later, it was permanently switched off because he started working for the Yankees. He began as a college intern in 1986 and worked his way up, becoming assistant general manager when the team won the World Series in 1996 and then serving as general manager for the last 27 years and winning four more championships.
As general manager, he is responsible for acquiring players, hiring staff and managing the day-to-day baseball operations of the team.
Now, his Yankees are in a perilous position, trailing the Dodgers two games to none in the World Series and facing a crucial third game at Yankee Stadium on Monday night. No one wants the Yankees to rebound and beat the Dodgers more than Mr. Cashman does, but there was a time when such a notion was unthinkable.
He grew up in Lexington, Ky., and his parents, John and Nancy Cashman, were from New York and virtually all of their extended family members supported the Yankees. Young Brian was an exception. For some reason he can’t define, he chose the Dodgers, perhaps because they were a terrific team in the 1970s.
But the 1977 and 1978 World Series were painful for Mr. Cashman, who was 10 and 11 when the Yankees beat the Dodgers to win both of those titles.
“I was devastated,” he said. “I thought I’d never see a Dodger world championship. But then in 1981 they broke through.”
The Dodgers beat the Yankees in the 1981 World Series, and a few months later, Mr. Cashman was invited to be a bat boy at Dodgers spring training. Ralph Branca, the former Dodgers pitcher, was a friend of Mr. Cashman’s parents, and he set it up. Mr. Cashman still credits Mr. Branca and his wife, Ann Branca, for nourishing his true love of baseball, thanks to that memorable day.
What Mr. Cashman recalls most strongly was Mr. Lasorda’s imploring him to pick up the bat as soon as it left the hitter’s hands, a sample of the signature motivational techniques that he often used with Dodger players.
“He would yell at me, ‘Don’t you let that bat hit the ground,’” Mr. Cashman said. “‘You get out there and get that bat before it hits the ground. I want to see you sprint.’”
Never one to back down from a challenge, Mr. Cashman did exactly as he was told and left an impression. Years later, Mr. Lasorda, who died in 2021, would joke that he had given Mr. Cashman his start in baseball, and that somehow Mr. Cashman still had more championship rings than he did.
Like many young fans, Mr. Cashman also wrote letters to the Dodgers, informing them that they had a young fan in Kentucky. They sent back signed photographs and letters, which Mr. Cashman cherished.
“I must have them somewhere,” he said. “I can still see that Dodger letterhead, and I remember the address: 1000 Elysian Park Avenue.”
(Today, the street is named after Vin Scully, the celebrated Dodgers broadcaster).
And there was the time he almost switched back. In 2005, when Frank McCourt owned the Dodgers, he tried to lure Mr. Cashman away from the Yankees with the promise of more money than even the Yankees were offering.
Mr. Cashman was tempted, and the Dodgers had it all planned out. They were going to present him as the return of the bat boy, a heartwarming story underwritten by millions of dollars. But in the end, Mr. Cashman decided he was no longer a child infatuated by Dodgers blue. He had come of age with the Yankees, under then-owner George Steinbrenner, who was overbearing and difficult to work for but also gave him opportunities.
“Loyalty was important,” Mr. Cashman said. “Whatever I was at that point was only because of the Steinbrenner family. So I declined the Dodgers offer.”
Since then, each team has won one World Series: the Yankees in 2009 and the Dodgers in 2020. The last 15 years have been a struggle at times, because Yankees fans expect the team to win the World Series every year, and some blame Mr. Cashman when they fall short.
In order to break that streak now, the Dodgers must lose. That was something that 10-year-old Brian Cashman could barely have stomached. But it is 57-year-old Brian Cashman’s mission.
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