The New York Jets selected O'Brien as the 24th pick in the first round of the 1983 NFL draft, shocking observers who expected the team to choose quarterback Dan Marino, a future member of the Pro Football Hall of Fame, who was selected three picks later by the Miami Dolphins.
The Jets fans who attended the draft, held in New York City, were surprised and outraged by the choice; O'Brien was so obscure that New York television reporter Sal Marchiano twice mangled his name while reporting on fan reaction to the draft.
")[1] Don Shula, who coached the division rival Miami Dolphins (which drafted Dan Marino later in the round) famously asked "Who's he?"
Years later, Mike Hickey, a Jets personnel director stated that O'Brien was chosen because he felt that he was smart enough to run the complicated offense of first-year head coach Joe Walton (hired after the firing of defensive-minded Walt Michaels), as O'Brien was reported to have an IQ of 130 to go along with an arm that would be ideal for Shea Stadium and its wind (the Jets moved away from Shea the season after drafting O'Brien to less windy Giants Stadium).
Hickey also stated that the Pittsburgh Steelers (three picks ahead of New York) not selecting hometown Marino was a key factor and that the final choice was between O'Brien and Darrell Green (later chosen by Washington and a future Hall of Famer).
On September 21, 1986, O'Brien engaged in a famous duel with Dan Marino when the Jets played the Miami Dolphins.
O'Brien threw 25 touchdown passes for the second-straight season and helped the Jets post a 10–6 record in 1986, but a sore arm bothered him down the stretch, which saw the team lose five games in a row to stumble into the playoffs.
[9] O'Brien only came in action for the divisional round game versus Cleveland when Ryan got hurt early.
He retired after spending the 1993 season with the Philadelphia Eagles where he started only four games and mostly served as a backup for Randall Cunningham and Bubby Brister.