The more I think about it, the more comfortable I am with the Bears signing Cutler. Last year was the most high powered offense in the Bears history. The only team that scored more points than they did were the Broncos. Yeah, he isn't the greatest quarterback and he wont air it out for 300+ yards each game, but the offense isn't the problem in Chicago. Cutler offers them stability and reliability.
Their offseason focus in terms of free agency and draft should be 100% focused on shoring up that god awful defense. Almost every pick in the draft should be a defensive player. Can't be any worse than what we got already.
Its thinking like this that landed you that seatbelt avatar last season. Even if we accept that Cutler's numbers are stable (and, frankly, they have been all over the place but I can put that down to the revolving door at OC), reliable is a big stretch. Notorious late game picks aside, his play is pretty pedestrian when you consider the shitty defenses he faced this year. He has nearly the same TD to TO ratio and passer rating as Flynn did this season. Not what I would be tying up cap money on, especially as a new coach. Yeah McCown is old, but this team needs a serious rebuild right now and the next set of viable QB prospects are likely to be seen in the 2015 draft. To me, it would make much more sense to retain McCown, tag and trade Cutler, and draft a solid rookie in two years and let him hold the clipboard behind McCown for a year before taking over and putting McCown out to pasture. As you pointed out, you need at least two years to retool the defense (and likely parts of the O-Line), anyhow, and shelling out big bucks to Jay is only going to make that harder down the road. Also, Packers are pretty much going to be going for exactly the same positions in the draft (as will the Steelers, Ravens, and Vikes), so Linemen on both sides of the ball are going to be a thin commodity and one that takes a year or two to develop to NFL level, anyhow.
The biggest thing here is the ability to sign descent FA. Packers simply won't because Ted does not hire guys on FA unless you hold a soldering iron to his balls, but that may happen this year in the defensive backfield, given the massive dropoff we saw this season after Ted cut Woodson lose. We need a leadership guy with better field awareness than Hawk calling the plays back there and Williams is going to want to take us to the cleaners with his next contract. Bears are kind of in the same situation, but much more likely to dip into free agency (and a little better at it). But if I am a veteran DB and have to options with tight cap situations, with those options being Rodgers or Cutler, who do you think I am going be more likely to sign with? That, to me, is the main problem with the Cutler contract and (no matter how minor) it fucks them down the road like Flacco's did for the Ravens, though at least the Ravens have a ring to show for their folly.
And yeah Brando, all the Bears had to do was win one game against a sub 500 team in their own house to get into the playoffs. A team without half of its starting defense and a third of its starting offense, yet that still managed to convert four 4th downs in the last drive to secure the win. I have a hard time imagining a more favorable scenario than that for the Bears, but we have been in this dance before where all they had to do was get by the Packers to advance (with Cutler, no less) and its always played out the same way. I personally did not want the Packers in the playoffs this year and think Rodgers was stupid for risking his entire career coming back this soon, but on the other hand at least we made the SF game look close and stopped the dumpster fire that is the Bears current team from making our division look bad with another 40-10 playoff "classic", like the Lions had been doing recently.