Cutler can make the same jump that we've seen from Joe Flacco and Eli Manning the past two seasons.
The past two Super Bowl winners have a lot of things in common: a solid (but not at-all-times dominating) defense, talented skill position players on offense, an offensive line that played better in the playoffs than they did in the regular season, and a late-season hot streak. The Bears seemingly have all those same components, except for a late season hot streak. With Marc Trestman in charge, hopefully the offensive line and the team in general can play hot when the weather turns cold, and give the Bears a chance to follow in the footsteps of the Giants and Ravens.
The Giants and Ravens both have one other thing in common: quarterbacks that announced themselves as "elite" before they actually played that way. Before the 2011 season, Eli Manning said that he was in the same class as Tom Brady, Drew Brees, and his big bro, Peyton Manning. Everyone scoffed, despite Manning's 2007 Super Bowl victory against the Patriots. Seven years into his professional career, Manning had one season (2009) with a quarterback rating above 86, and was coming off a 2010 season where he had 25 interceptions. In 2011, Manning had one of his best seasons with a 92.9 rating, 29 touchdowns and 16 interceptions, and a 8.4 yards per attempt average. His postseason was even better, throwing nine touchdowns and only one interception over four games and had a rating of over a hundred in three of those games.
Flacco, on the other hand, didn't just declare himself elite. Before this season, he said he was the best quarterback in football, despite having only one clearly above-average year. That year was 2010, when Flacco had a quarterback rating of 93.6 and threw a career-high 25 TDs (versus 10 INTs). 2011 was his worst since his rookie year, with career-lows of 6.7 yards per attempt and 57% completion percentage. Flacco set aside numbers proving his averageness, and placed himself at the top of the quarterback mountain without any true evidence that it was even a possibility.
The regular season for Flacco was a step above his average season, with 22 TDs, 10 INTs, a career-high 3817 passing yards, and a 87.7 rating. Not top-5 numbers; in fact, Flacco ranks between 12-15 in most quarterback statistics. But again, just like Eli, the postseason was the difference maker: four games, eleven touchdowns, zero interceptions, every game with a rating above one hundred. Before this postseason, Flacco had nine playoff starts, and only one was comparable with anything he did this postseason, and that was against the Chiefs in 2010.
Jay Cutler has a chance to make a similar jump as those two, and obviously the first step is to declare himself an elite quarterback. Seriously. The confidence that Eli and Joe had to declare themselves elite means something, even though just saying it doesn't make it so. Confidence isn't something Jay has a problem with, but he needs to embrace it like those two did.
Manning and Flacco made their statements and were derided for it; no one thought they would lead their respective teams to a Super Bowl win. Their regular seasons were above-average, but not indicative in any way of the kind of playoff performance they would put on en route to holding up the Lombardi trophy. They announced their confidence in their respective abilities, and were given a chance to prove it on the road through the playoffs, and they backed it up.
Obviously quarterback play isn't the sole reason for the Giants and Ravens winning the past two Super Bowls, but we can look back at the past two Bears' seasons and clearly say that if Cutler played better down the stretch in 2012, or at all in 2011, things may have gone a lot differently in Chicago. Cutler has a chance to make a leap forward like Eli and Joe; he has the team around him to get it done, a front office determined to improve the offensive line, and a coaching staff itching to work with Chicago's star quarterback. And like the last two Super Bowl winning quarterbacks, Cutler doesn't have to prove his elite status in the regular season, he needs to step up in the postseason.