I don't think that Callahan will be worth more than 5M within three years of today. I could see Callahan not ever hitting 25g again, already. Realistically, a player like Callahan is not someone I would want to pay more than 4.5M even with the cap rising right now. For his intangibles and since he's our captain and a homegrown player, I can stomach paying a premium, but I wouldn't go beyond 5.2M, and I think that at that number, he is clearly overpaid.
Callahan is the definition of a glorified third liner. I don't say it as an insult and I'm a big fan of Callahan. I just mean that, factually, he's an ideal third liner who gets glorified into something more because of his "leadership, grit and great two-way play". Do you guys think this team would be SIGNIFICANTLY worse if you replaced Callahan with Sobotka in our lineup? I don't. Callahan is not, even remotely, irreplaceable. He was irreplaceable when he was a relatively cheap, cost controlled, younger player playing in a system that fit him like a glove. At this stage of his career, especially when you start discussing players in the 4.5-6M range, Callahan can easily be replaced with better results than paying him 5-6M for 6-7 years.
That simply has disaster (or perhaps, more aptly, "Drury") written all over it. I loved Chris Drury too. Loved him in Buffalo name loved him his first couple of years here. There just came a time when he was getting paid for much more than he was capable of. That's what's going to happen to Callahan in 3-4 years. A player like Callahan, at anything above 4.6M or so, is a luxury, not a necessity. I just don't think we need to spend the money it's going to cost to keep him on this roster.