For me, a big win today looks like: Lindholm or Stamkos, Zadorov or Montour, see what's possible with Marchessault/Toffoli/Teravainen (obviously a 3rd notable addition depends on what combo of players we're talking about). All signs say that Stamkos will hit the market but I'm still not 100% assuming that - maybe 98% at this point. I will say that I would opt to not sign a big name on D if it means they can grab 2 big names at forward.
A fairly big miss today would look like: Monahan + Dillon. They need to make a much bigger impact to the roster than this. No offense to that caliber of player but those are the types you add at the trade deadline to get ready for your playoff push.
I'm not really big on bringing back Bertuzzi. He's okay but runs hot-cold and isn't quite as gritty as he looks. Maybe if he's like the 3rd wheel added today. I'd possibly rather add the annoying but still capable David Perron if there's no hope of getting one of the better wingers.
Like previous posters have said, whatever $ you are hoping a player can be signed for, probably add 10-25%. They have all turned down pretty good offers already and will have multiple suitors. The Bruins need to add some top shelf talent (prioritizing up front) and will have to really compete to make that happen.
Edit: And Bertuzzi is already off the board while I was typing that. The free agent pool has shrunk a fair amount already with several big names off the board yesterday and today.
So let me ask everybody: Are you nervous about whether Boston will be able to add the type of players today (or the next few) you think they need to add?
I have to say, I'm nervous about whether they get it done.
