Yankees legend John Sterling shares one regret about retirement decision

Legendary New York Yankees radio announcer John Sterling is somewhat haunted by one regret regarding his immediate retirement that he and the Yankees confirmed last month.  

"Looking back, I have a great boss in (Audacy New York market president) Chris Oliviero," Sterling explained during a chat with Derek Futterman of the Barrett Sports Media website. "He’s so nice to me, so good to me. I should have told him March 1 – I knew (about the retirement decision) then. I should have told him March 15 – I knew then." 

Sterling ultimately remained with the Yankees through their season-opening road trips to the Houston Astros and Arizona Diamondbacks. Those experiences helped convince the 85-year-old that it was time to step away. 

"So I went on that trip, and afterward [it was], 'I don’t want to do this anymore – I’m tired. I’ve done this long enough,'" Sterling said. 

Sterling began calling Yankees games in 1989, but had welcomed a lighter schedule in recent years even before Oliviero offered the icon an opportunity to call only home games this season. 

"I just didn’t have the desire," Sterling said about rejecting that proposal. "Like today, to get up, make myself beautiful and go to Yankee Stadium to broadcast a game – I want to sit back, lie on my bed and watch hockey, basketball and baseball together." 

Sterling's personalized home-run calls for Yankees players made for entertaining viral moments across platforms such as ESPN and MLB Network. As Futterman mentioned, the Bronx Bombers now play a version of Sterling's signature "Yankees win!" phrase following home victories before Frank Sinatra’s rendition of "Theme From 'New York, New York'" blares over the stadium speakers.