Dee was a three-sport letterman at the College of the Holy Cross who was one of the first players signed by the Boston Patriots of the AFL in 1960.

Despite equipment improvements over the years, Dee was a superstitious player who chose to wear the same helmet throughout his career (105 of 112 games).

[citation needed] Dee etched his name in the history books by scoring the first points in American Football League history, scoring a touchdown when he dove onto a fumble by Bills QB Tommy O'Connell (father of former Boston Bruins GM Mike O'Connell) the end zone in the second quarter of the league's first-ever exhibition game, a contest between the Patriots and the Bills on July 30, 1960.

Dee sacked Frank Tripucka, Al Dorow, Hunter Enis, Jacky Lee, MC Reynolds, Randy Duncan, Cotton Davidson, George Blanda, Jack Kemp, Johnny Green, John Hadl, Tobin Rote, Len Dawson, Eddie Wilson, Dick Wood, Joe Namath, Tom Flores, Rick Norton and Bob Griese and recovered fumbles by Al Carmichael, Art Baker, Wayne Crow, Jacky Lee, Paul Lowe, Bill Tobin, Wray Carlton & Max Chobian.

On July 22, 1968, Dee announced his retirement from professional football, citing a business opportunity that was "too good to resist."