Ken Singleton, New York Yankees
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With over fifty years in baseball, Ken Singleton has seen it all.

Fifteen years as an outfielder with the Mets, Montreal Expos and, most memorably, the Baltimore Orioles. Another 37 in the broadcast booth, over 20 of which came with the Yankees on MSG Network and YES. All along the way, Ken Singleton seemed to meet anyone and everyone associated with Major League Baseball.

Imagine growing up listening to Vin Scully call games for the Brooklyn Dodgers, only to be a professional player 20 years later and meet him in person in Los Angeles. Similarly, Singleton played winter ball in Puerto Rico early on and had Roberto Clemente as a manager.

The list goes on. Larry Doby, the first Black player in the American League, was Singleton’s hitting coach in Montreal. If you ask Ken, Doby’s the one who taught him to balance contact and power. In Baltimore, Earl Weaver seemed to plan his ejections on a game-by-bame basis while also utilizing on-base percentage well before it was considered a relevant stat.

“There’s nothing like being a Major League player,” he said. “I did it for 15 years and played for some very good teams and got to a couple World Series and a few All-Star games, but broadcasting is a close second. It keeps you around the game. I feel like it’s kept me younger because you’re around all these young players.”

Ken Singleton recently sat down with ESNY’s Yankees podcast, “Bleacher Creatures,” for its 150th episode. If there’s anyone who’s had a baseball life well-lived, it’s him.

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Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.