Born in Chicago, O'Connell was a star athlete at South Shore High School area, playing for the city prep championship under former Illinois coach Clarence Applegran.

He was recruited by Notre Dame but elected to play with his former prep teammates Rex Smith and Pete Bachouros at the University of Illinois Urbana-Champaign.

He passed for 692 yards and six touchdowns that year as Illinois went 9–0–1 and won the Big Ten title to go along with the 1952 Rose Bowl (it is to date the last time the Illini have had a season with no losses).

Midway through the 1956 season, he signed with the Cleveland Browns, who needed a backup quarterback for Babe Parilli after previous injury to George Ratterman.

In the penultimate game of the year, he suffered an injury to his fibula that saw him have three hairline fractures in his leg that was initially stated to be an ankle sprain.

The following year, he was hired the 18th head football coach at Drake University in Des Moines, Iowa and he held that position for the 1959 season.