Born and raised in Lyons, Bob Deegan graduated from Morton in 1957.
He excelled in football and made the Illinois All-State Football Team, along with classmate Ron Miller, who was the quarterback for the All-State First Team. Bob earned a football scholarship to attend the University of Minnesota, where he played for three years alongside Bob Prawdzik, another Morton grad. Deegan and Prawdzik played in the 1962 Rose Bowl against the UCLA Bruins, which they won 21-3.
In the 1961-62 season, Minnesota played a game against the University of Missouri in which Deegan and Prawzdik were the starting ends for Minnesota and Jim and John Sevick, also Morton grads, were the starting ends on the Missouri team.
After graduating from Minnesota, Bob played in the Canadian Football League with the Winnipeg Blue Bombers and the Saskatchewan Roughriders as a defensive end.