All NHL contracts are guaranteed. They insure them so if an injury happens then the insurance company pays out the money rather than the team.
True, all contracts are guaranteed, but I wouldn't be so certain that the Pens will be able to get Crosby's new deal insured. Or, more accurately, I wouldn't be certain that the Pens will find it cost effective to get the deal insured.
If the likelihood of him not playing out the contract due to injury is 50% (for kicks), then any insurance policy would cost 50%+, probably more likely ~70% of the contract value) as the insurance company is not planning on losing money by issuing insurance policies.
I think it's a pretty smooth move by the Pens. You sign him up for 8.7 million. Surely he's worth that for his on ice, off ice, ticket selling, advertising ability. If the new CBA has a rollback his contract gets included in it (I would think) and you get him for whatever % less. If you wait until after a possible rollback you still would need to sign him for the 8.7 million aye?
If the maximum player salary drops below $8.7MM after the new CBA becomes effective, you wouldn't be able to sign him for that now would you and would no longer 'need' to sign him for $8.7MM/.
But, yeah, it probably will work out for the Pens IF they are able to get the contract insured, as him getting his brains splattered this November and making him unable to play again would probably make him less valuable than $104MM or so. If they didn't / don't get the contract insured, then it is a VERY ballsy move, and one I'd expect a hockey player rather than a businessman to make.