First, they have to draft a receiver and get Devin Hester back to returns. The Bears will still be playing a field position game, and Hester is one of the most dynamic special teams threats in NFL history. It's fine to have him still running a few go routes to keep defenses honest, but the "#1 receiver" myth needs to stop. Cutler will need receivers who are reasonably quick, with good hands, who run precise routes. As a receiver, Hester's still very much a work in progress. They can still get a quality receiver, like Hakeem Nicks or Brian Robiskie, in the second round.
There is also the interesting personal and professional dynamic between Cutler and Earl Bennett, who played together at Vanderbilt. Selected in the third round by the Bears in 2008, Bennett took time to understand the offensive system and didn't catch a pass in his rookie year. But Cutler thought enough of Bennett to take time to throw at Bennett's Pro Day, and that's not something established NFL stars generally do. In 2005, Bennett caught 79 passes for 876 yards and nine touchdowns from Cutler. And in his first two collegiate years, one with Cutler and one without, he caught more passes than any other SEC receiver. Bennett could be a surprise for fantasy players and Bears fans in 2009.
Second, the Bears must upgrade their offensive line, and they've taken steps to do that, acquiring Kevin Shaffer and Orlando Pace. Part of the reason Cutler played so well last year was that he had great pass protection all year, especially from dominant rookie left tackle Ryan Clady -- he was sacked 11 times in 616 pass attempts. Cutler has a good outlet underneath in Forte, who led the team in receptions in 2008, and that will help the pass protection.
Third, the defense must hold fast. In 2008, they ranked second in the NFL in Defensive Adjusted Line Yards, and 27th in Adjusted Sack Rate. They need to bring more pass pressure, and provide more solid coverage. Quarterback Wins is the single dumbest stat in football, but it's a lot more indicative when you throw qualifiers in there. When Cutler's team allows 22 points or less, his "record" is 12-1. Denver's defense was atrocious last year, which throws his overall W-L into the realms of the useless.
If Chicago's defense stays solid, they'll complete for at least the division with Jay Cutler. If not, Cutler will find himself in a "new team, same situation" scenario.And the Bears will have spent a lot for a little.
Doug Farrar is the Publisher of Falcon Insider. He also writes for Football Outsiders, the Washington Post, ESPN.com, and the Seattle Times. Feel free to e-mail Doug here.