And Chicago Bears fans can't help but worry that he packed the baggage along with his prize rocket arm.
It's no secret the team gave up a plethora of benefits to secure Cutler, including first-round picks in 2009 and 2010 and former Bears quarterback Kyle Orton.
"Any time a team is going to make a trade and give up what the Bears did to get me, then the expectations are going to be very high," Cutler said. "People are going to be wondering what I’m doing and how I am getting ready for the season."
But what many fans are not aware of is the baggage that Cutler assuredly brings in the form of a blood sugar monitor he is dependant on since his diagnoses of type one diabetes last April.
Cutler insists, however, that his many athletic abilities, including his infamous 60 mph football throw, will not be affected.
"As long as I stay on top of it there is absolutely no change over two years ago," Cutler said. "If we don't regulate it or stay on top of it you get tired, you get sleepy, you get worn down easier. But you know with the doctors of the Bears and the trainers and everyone staying on top of it, it should be smooth sailing this year."
And as for his notoriety as a “petulant” quarterback, Cutler does not use his diabetes as an excuse, but does acknowledge a shift in his attitude that can be attributed to the illness.
"You do get moody, depressed, get irritable, and you are just hard to deal with," Cutler said. "Now whenever I get up into the 200s or 300s I start to snap at people."
Along with Pro Bowl quarterback, Cutler accepts the moniker of diabetic and wants to turn it into a message of positivity for kids with the illness.
There is one other title Cutler wouldn't mind adding next to his name. Super Bowl quarterback.