Michael Kay tried talking John Sterling out of retirement

John Sterling retired at 85 after 64 years as a broadcaster, but according to Michael Kay, it was still too soon.

Kay joined the New York Post’s Jon Heyman and Joel Sherman on their podcast, The Show, this week to honor Sterling, his former broadcast partner, who passed away Monday morning. And while Sterling was known for his longevity, having worked 5,060 consecutive Yankee games from 1989 to 2019 before retiring in 2024 at the age of 85, Kay believes he could have continued working.

“I think one of the things that led to him retiring, he just got frustrated that there weren’t newspapers, physical newspapers available on the road anymore,” Kay said.

Kay recalled telling Sterling’s kids to buy him an iPad one Christmas so he could finally have every newspaper at his fingertips. And while they gifted Sterling an iPad, he refused to use it. The closest Sterling ever got to technology was his flip phone. But even with his flip phone, Kay said Sterling kept all of his contacts and numbers written on a sheet of paper in his pocket.

“If he had somehow leaned and gotten comfortable using an iPad, I think he could have still been broadcasting,” Kay said. “I did try to talk him out of retiring because I think of Bear Bryant and Joe Paterno, when older people retire from something that is so much a part of their life, health becomes an issue.

“Maybe that’s just because of age. But I said, ‘John, the Yankees are bending over backward for you, they’ll do anything for you, they’ll give you any schedule.’ They had cars pick him up at his home and drive him back.”

Sterling did have some health issues prior to retirement that forced him to miss games in his final years with the Yankees. He maintained the job of calling a baseball game was still easy when he retired, but Sterling told Kay just the walk from the car to the booth was becoming too much, even as the Yankees attempted to make travel as convenient as possible.

Fans still enjoyed listening to Sterling, and it certainly seems like the Yankees were willing to do whatever it takes to keep him in the booth as long as possible. But working into your mid-80s after 64 years as a broadcaster is a heck of a career.