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.