Keynan Middleton is entering a fourth straight offseason of MLB free agency, and while he wouldn’t mind finding his way back to the Yankees bullpen next year, he has his side hustle to keep him busy in the meantime: assistant varsity basketball coach at Rex Putnam High School in Milwaukie, Oregon.
The 30-year-old Middleton spends February through September of every year pitching, but feeds his other passion each winter by coaching high school basketball back home.
After spending the past nine offseasons as an assistant coach at his alma mater, Milwaukie High School, in a suburb of Portland — including three years as the head JV coach — he is joining their rivals this offseason at Rex Putnam, the former high school of Scott Brosius.
“I’m really excited about it,” Middleton said on the final weekend of the regular season. “That was something that when I was in the minor leagues and I didn’t even know I was going to be a big leaguer, ever, that was my fallback plan.



