Longtime New York Yankees announcer Michael Kay, 65, has begun contemplating his retirement, describing the prospect as "awkward" due to the ages of his children. Kay expressed doubt about continuing to call games into his 80s, drawing a parallel to the late Yankees radio announcer John Sterling, who retired at 85 and passed away in May 2026 at age 87.

Kay, who has been a Yankees announcer since 1992, initially working in radio before moving to the YES Network in 2002, noted that conversations about retirement typically arise around his current age. "65 seems to be a magic number," Kay said in a podcast appearance. "And I’ve actually been thinking about the end. When do you walk away? When is it the right time? Because of my children’s ages, it’s kind of awkward."

His son is 11 and his daughter is 13. While Kay works from home four days a week during the winter, allowing him to be present, he anticipates a shift when his children enter college. "When Callie goes to college in five years, and Charlie goes to college in seven years, what am I going to do if I retire?" he questioned.

Kay admitted, "I don’t see myself being alive in my 80s." However, he added that even if he were, he doesn't envision himself still broadcasting games, though he acknowledged one should "never rule anything out."

He referenced Vin Scully's adage, "God laughs at those that make plans," suggesting a degree of uncertainty in life's trajectory. Kay is amazed that Sterling, who called games for decades, reached his age and length of career.