I'm not sad to see the Bears fumbling away their legacy as an organization- they are quickly turning into the NFL's version of the cubs. Sometimes competitive enough to tease, always missing something important to make them legitimate hopefuls to win it all (see: amazing defense AND Rex Grossman vs. Peyton).
I am disappointed for Trestman. He is a consensus excellent person, and his real strength in his time in the CFL was that he was able to create a consistent and self-perpetuating culture of excellence and community within his locker room. You won't find a player who played for him during that time that doesn't speak highly of the dynamic he was directly responsible for that was the key factor in the incredible run of success the Montreal Alouettes enjoyed under him.
I think two things played against him. If you haven't figured out that the first was Jay Cutler/Jeff George, let me put in on record. The guy is an absolutely frustrating beast. Except for the fact that post-Holmgren Favre actually helped us win enough to make it to two more NFC title games before destroying our hopes with mindbendingly stupid decisions, Cutler plays exactly like mindbendingly stupid decision making Favre game in and out, except that he's utterly unlikeable while he does it. AND, he doesn't want to learn how to play less stupidly. Coach killer...
The other thing is that Trestman isn't Mike Ditka. He's a softspoken guy who looks more like an accountant than a football coach in a city where people want their HC to be a Godzilla clone. People don't realize that Trestman not only had the full and complete backing of ownership during his tenure in Montreal, but he also had a tremendous working relationship with his GM, who was an excellent talent evaluator, scout and opportunist in terms of getting good return on long shots and cutting loose when they didn't turn out. Trestman didn't have either an ownership group willing to stick to a long term plan that would yield results (I think this has everything to do with recognizing the millstone that Cutler's deal is to the entire organization for the foreseeable future), or a GM with personnel acumen to speak of.
In any case, he's not likely to get any HC looks in the NFL again for a very long time, but I'll be interested to see if he gets a call to work as an OC. With a building block piece in place at QB who needs development and consistency, he'd be an unreal fit. People can snicker about the Canadian Football League, but Trestman had a huge role in helping Anthony Calvillo become one of the greatest passers in a pure passing league's history. Here's hoping he gets an earnest shot at a job where his talents and approach have an opportunity to show how valuable he is.
And I can't wait to see the retreads the Bears shuffle out as the architects of three more years of Cutler-lead misery.... Who knows- they might be on the hook for fired coach and GM salaries equal to Cutler's annual cap hit before they realize it might just be wise to eat his hit and rid themselves of the cancer killing their whole team. Here's hoping.