He came close last year, but he was ineffective in the NFC Championship Game in a 21-14 loss to the Green Bay Packers.
No. 6 has been an enigma in Chicago, showing flashes of brilliance coupled with questionable play.
With his contract expiring after the 2013 season, will Cutler lead the Bears to the Super Bowl?
Jay Mariotti termed the Chicago Bears as "The City of Weak Shoulders" as a crack to their extremely poor quarterback situation.
The Chicago Bears have had 18 starters during Peyton Manning's consecutive-start streak and sometimes went through three or four starters in a year, as in 2004 (Chad Hutchinson, Jonathan Quinn, Craig Krenzel and Rex Grossman).
General manager Jerry Angelo then traded two first-round picks and Kyle Orton for Cutler in 2009, and the Vanderbilt product has thrown some big numbers.
Cutler has 7,900 passing yards (sixth all-time on team) and 55 touchdowns (seventh) while playing just two-and-a-quarter seasons. He is also the first quarterback in franchise history to throw 3,000-plus yards in consecutive years.
Compare that again with 2004, as the four-headed monster at quarterback just managed 2,641 yards through the air for nine touchdowns and 16 picks.
By this rate, he could challenge the Hall of Fame Sid Luckman's team records of 14,686 yards passing and 137 touchdowns.
Even with Cutler's talent, he is not the best or even second-best quarterback in the NFC North.
Both are younger than Cutler and have potent offensive weapons that Cutler lacks.
Rodgers, who led the Packers to a Super Bowl win, is playing like a young but less turnover-prone Brett Favre.
Rodgers has 1,325 yards passing for 12 scores and just two picks. He can also run the ball, getting two rushing tallies against the Denver Broncos.
Unfortunately, Stafford is also in Cutler's way.
Now healthy, Stafford has 1,217 yards for 11 touchdowns and three picks. Stafford has created an elite duo with Calvin Johnson, as the two have eight touchdowns in 2011.
For the past two-plus seasons, Cutler has been a human pinata as his offensive line has done a pitifully poor job protecting him.
He has been sacked 107 times with the Bears, including the postseason.
In addition, Cutler has been hit and knocked down countless times, resulting in a torn MCL in the 2010 playoffs and a kick to his throat against the Saints.
However, No. 6 just keeps standing right back up and coming back to work the next play and next game.
He has missed only one game due to a concussion, and that was after being sacked nine times in one half.
He has the toughness and the drive to succeed and lead his team to success.
The Bears offense lacks offensive firepower, and the whole league knows it.
The offensive line is horrendous for two years running now.
Linchpin Olin Kreutz is now with the Saints. Roberto Garza shifted to center, weakening the right guard spot.
Chris Spencer and Gabe Carimi have injuries, and right tackle Frank Omiyale should never play football again, as he is a revolving door for defensive linemen and linebackers to kill Cutler.
Wide receiver and tight end are also glaring weaknesses.
Devin Hester and Johnny Knox drop passes, Earl Bennett can't seem to stay healthy and Roy Williams looks done. The Bears also shipped off Greg Olsen to Carolina, who had a touchdown grab against the Bears on Sunday.
Chicago does have Matt Forte, but he is sometimes inconsistent in the run game (a combination of poor O-line blocking and not creating his own holes).
Meanwhile, the Packers and Lions offenses are thriving.
Rodgers is equipped with a solid offensive line, and he has weapons in Jermichael Finley, Donald Driver and Greg Jennings. Detroit has Calvin Johnson, Brandon Pettigrew and Jahvid Best.
Jay Cutler has shown some improvement this season, due to hard work in the offseason.
He led team practices during the NFL lockout and looks more comfortable in offensive coordinator Mike Martz's scheme.
He is stepping up in the pocket more often and his decision-making has improved, as he has cut down throwing on bad passing situations.
When Cutler is protected, like in Week 1 against the Atlanta Falcons, he passed for more than 300 yards and a couple scores.
Keep in mind that Cutler has thrown almost 1,000 yards without his favorite targets Bennett and Olsen.
Jay Cutler has had a target on his back since he left Denver.
Players seemed to be jealous that he got traded to a team he wanted as a young player while signing a long-term, lucrative contract.
They tore into him after he tore his MCL and had to leave the NFC Championship Game against the Packers.
The media is also taking jabs at him, as Fox Sports made up Illinois newspaper headlines questioning Cutler's "toughness" by not returning to the field after his serious playoff injury, which would have kept him out four to six weeks.
While not criticizing Cutler's talent, the Chicago media wants winning results. In the playoffs, the Chicago Sun-Times questioned Cutler's ability to lead the Bears to victory in the playoffs. Also, Mark Portash wrote how an elite quarterback needs to do more than throw.
Cutler can't get a break with his personal life either, as the media is attacking his romantic relationship with Kristen Cavallari from all angles.
With all these distractions, Cutler will have a harder time focusing on his gridiron play.
Unfortunately, Cutler will not lead the Chicago Bears to Super Bowl glory before his time is up.
The Bears are not surrounding No. 6 with enough offensive firepower to make the most of his talents.
The offensive line could also let Cutler suffer a devastating injury with its porous "protection."
Not even internal pressures are the whole story. With the Packers and Lions at the top with better, younger quarterbacks and the media's constant unfair jabs at Cutler, he is not in a good position to succeed.
What are your thoughts? Feel free to post your comments.