After attending Stamford High School, he first enrolled at the University of Alabama, but left as a sophomore to manage the family restaurant after his father became ill.

[citation needed] The Dallas Cowboys selected Dugan in the 1960 NFL Expansion Draft, where along with Billy Howton, became the first wide receivers ever to start for the franchise.

That year, he was the second leading receiver on the team (behind Jim Doran), while earning a reputation for spectacular catches and producing 29 receptions for 461 yards and a touchdown.

The Redskins acquired Dugan, placekicker John Aveni, defensive back Dave Whitsell and offensive end Jerry Daniels.

[2][3] Dugan flourished with the Redskins in his first season, breaking the team receiving record and setting career highs with 53 receptions for 817 yards and four touchdowns.