The question is what players will teams be willing to part with. Draft picks are fine, but the Jackets can't have a roster of 18 year olds next season or expect to make major free agent signings.
Bubble teams are going to want to add, not subtract. They may be willing to give up draft picks, but what about prospects? Rather than just getting a bunch of random pieces, what about getting key players.
Like what player or prospect would Brassard + Letestu get in return?
You're expecting rational behavior at the most irrational time of the year. Good GMs can make great trades, great GMs can go further because they can fuel the paranoia. There's a part in "Moneyball" where Billy Beane is trying to convince the GM of the Expos to pry a prospect loose from Boston (Kevin Youkilis) by doing exactly this. The Expos had Cliff Floyd, the Red Sox needed to add someone of Floyd's caliber and position, and everyone knew it. Beane, an uninvolved third party, loved Youkilis and saw this as his chance. During the conversations, he kept telling the GM of the Expos that the fans of Boston would hang their GM if the only thing that prevented the Red Sox from winning a World Series was a first baseman playing double-A ball who wouldn't be in the majors for another three years.
San Jose is looking at a closing window. Minnesota has underachieved despite making a huge splash in free agency. Detroit may be looking to hang on for another year or two. Toronto and Montreal are doing unexpectedly well. Anaheim has four major UFAs and might want to make a last shot. And so on.
In cases like this, grafting the pieces in (regardless of fit or contract situation) will become a priority. Would Montreal let themselves be shoved around and out of the playoffs in one round rather than spend a 2nd on a guy like Jared Boll? If there's a key player on a playoff team who's fighting off an injury, do they try to pick up a replacement and deal with the roster logjam later?
I can see at least four or five teams going all-in at the deadline. And when they do that, they may well be blowing off their own foot when the contract situations clear. This could be an incredible year to stockpile assets, and then clean up in free agency when those same teams have to pay the piper.
I need to find a list of all the trades made by MLB GMs at the winter meetings back in their heyday. The days when cigar smoke was thick and the drinks were stiff. Major deals that would shape the face of a franchise or of the league for years to come were talked about and agreed upon in minutes or hours, not over the span of days. The NHL deadline is the closest thing that we see to this, where a lot of guys shoot from the hip and then get remorse weeks later.