Not a chance Chiarelli goes near him, the Bruins D for the most part is a pretty physical group and all can skate better then him, it would be a poor match much like Kaberle and Corvo were in Boston. I also think Chiarelli was in Ottawa when Redden started his deep decline, that alone would scare him off being privy to what was going on.
Chiarelli has a fetish for ex-Sens. Chara, Schaefer, Eaves, McGrattan, Kelly, Hnidy, etc.
I'd still say I'd take him (Redden) as the 7th "pressbox" guy, and if he happens to play well enough to play his way into the top-6, good for him. The last thing I want is for a guy like Boro or Weir, guys who are at the point in their careers that they need to play games in order to further develop, to sit in the pressbox for 60+ games this year. 7th defencemen are always best when they're older vets: if they sit for long stretches, it's not like you're stunting their development.
Worst case scenario: you pay Redden to be the pressbox cheerleader, add a veteran voice, and have a guy who can play in emergency situations.
Bet case scenario: he plays bottom pairing minutes.
Either way, IF we're not going out to add another roster player (and that's the key: there are guys I'd like to add before Reds, but if that's not going to happen...), it's worth a bit of a gamble IMO. You're out, literally, NOTHING if he doesn't pan out. A 1-year deal for like a mil. If he truly has lost everything, like I said, you stick him in the pressbox and he can help the young guys during practice.
Honestly, I think a chance to play in the NHL again might be enough of a motivator for him to be able to play effective 3rd pair minutes.. light a fire under his arse and really get him out of whatever shell he's developed playing in the A. That is a TOTAL gut call, though. I'm not basing that on any real evidence.
All that being said, I won't be heartbroken or anything if we don't sign him. I just don't think it'll be the end of the world if we do.