Russ Ryan used to think playing baseball was life’s greatest pleasure. Then he became a father. “I’d be in the stands debating if I enjoyed playing more or watching my son play more,” he says. After years of coaching and watching his oldest son, Andrew, he’s now found his favorite role: teammate.

“Being on the same field takes playing to a new height,” Mr. Ryan says. “There’s no feeling like being on base and having my son hit me home, or vice versa.”