John Riley graduated from Madison West high school in 1936. He enrolled in the University of Wisconsin just after his favorite sport hockey, had been dropped by the University.  So he proceeded to letter in tennis.
 
He continued to play hockey for the Madison Cardinals, a men’s team comprised mainly of university students. Before and after World War II, Riley starred for this team.
 
By the late 1940s and early 1950s, Riley became involved with developing another generation of Madison hockey players. He instructed and coached numerous youth teams and in 1962, his Madison Hawks won the national juvenile title.
 
In 1963, he was hired part time by the University of Wisconsin to coach the revived University of Wisconsin hockey team. In three years, the team compiled a 34-23-3 record. The stage was set for the University to hire a full time hockey coach.
 
On February 22, 1966, the University of Wisconsin defeated the University of Minnesota 5-4 in overtime. It was Riley’s most significant win. The story that is remembered has Riley predicting a Wisconsin victory that afternoon at the Blue Line Club luncheon.