Now in Tampa, McCown has gone from working with one of professional football's great offensive minds to one of the NCAA's most widely respected quarterback gurus of the past two decades in offensive coordinator Jeff Tedford.
As it turns out, McCown has Aaron Rodgers to thank for his new tutor.
Buccaneers coach Lovie Smith told NFL Media columnist Michael Silver that he reached out to Tedford last November after receiving a glowing recommendation from former NFC North rival Rodgers, who developed into a top prospect under Tedford's guiding arm at Cal.
Smith then flew Tedford to Chicago to see if their philosophies would mesh.
"Hey, we were both unemployed," Smith explained to Silver. "He's got a long history of (developing) guys who made it to this league. Also, I knew he'd be refreshed."
Rodgers isn't the only college star to succeed under Tedford.
In stops at Cal, Fresno State and Oregon, Tedford had a hand in the development of Trent Dilfer, Kyle Boller, Joey Harrington, Akili Smith and David Carr -- all of whom went on to become first-round NFL draft picks.
If Tedford can transfer that magic to the NFL level, McCown and the Bucs could surprise as an NFC South title contender this season.