I'm so freaking torn on this whole issue, it drives me crazy!
On the one hand we have the rapidly increasing cap - Ola is entirely correct in that very few of the long-term contracts signed the 4 years before the lockout look bad now, in fact most of them look like complete steals.
Everyone was up in arms over Skinners extension at the time - that deal is amazing right now. Erik Karlsson makes $6.5M, he'd fetch $10M+ on the open market. Let's not even mention Tavares.
Now I know that they were RFA's at the time but the point still stands - most of those cap hits looked at least "reasonable" at the time but are now steals.
Therefore I'm completely at peace with extending Girardi even though I think he is overrated, as long as it doesn't interfere with extending Strålman, since his cap hit won't be a problem going forward and he has an important role on the team.
The problem with Callahan is threefold.
1. Unlike Girardi who seems to ask for slightly more than he is worth, Callahan is asking for significantly more than he is worth.
2. We all know he is going to break down sooner rather than later, Drury-like red flags here.
3. And this is probably the most important one: He has lost his role on the team. If he was solidly cemented in the role as 2RW and a staple on the top PP I wouldn't have a big problem with extending him even at a steep price. Sure he may break down, but he'd be a significant part of the team and who knows - with the cap going up it may not be that big a burden anyway even if he turns into Brenden Morrow. But considering he doesn't have a permanent spot on the PP and that there are two players at his position that are significantly better 5v5 a big contract makes no sense at all. I'm sorry, but he needs to go.
My plan would therefore be to trade Callahan for a stop-gap for this playoff run and futures. Bank on a kid like Fast taking that role next year. And use the cap space to extend our current players to long-term contracts.
Take the short-term hit for the long-term gain. Lock up Zucc to an 8-year deal at ~$5M, Brassard at $4.5M, Hagelin at $4M, Strålman at $4.5M, give Kreider a back-loaded deal at a ~$4M average, Stepan $5.5M, Girardi $5.5M, Staal $6M. Early extensions are great because they are negotiated versus a lower cap and market than the one the contract takes effect in.
I'd even consider keeping Richards, but that would make the cap tight in 2014-15.
Many of those contracts may look ridiculous now, but they will be gold in 3-4 years.
Hell, even Kevin Klein's contract might look good in a few years.