NHL doesn't have a leg to stand on, because they have two?

CAA is the biggest and most powerful agency in the world, and it's arguably the most successful agency ever. They've done more contracts than anyone. And they have lots of lawyers. So I take it seriously when they speak. Even if I don't agree with them.

NHL can’t win Ilya Kovalchuk contract showdown, says prominent agent
The National Hockey League [...] may not have a legal leg to stand on in its rejection of Ilya Kovalchuk's [...] contract [...], one prominent agent said Wednesday. J.P. Barry of CAA Sports, whose large roster of clients includes Vancouver Canucks forwards Daniel and Henrik Sedin and Mason Raymond, said he doesn't see how the league can win [...]

"I have already done quite a few contracts that were front-end loaded and there is no language in the CBA addressing the term of contracts," Barry said. "So I am not sure what grounds they intend to rely upon." Barry has negotiated front-loaded contracts in recent years for the likes of Dany Heatley, Daniel Alfredsson and Mattias Ohlund, but none of those deals flatline in the final years quite the way Kovalchuk's does. [...]

"Obviously, there is no contract that has ever had the maximum and the minimum in the same deal and there is no contract that has had five minimum salaries going out the back end and there is no contract that takes a player past age 42," Barry said.[...]

Barry doesn't think the NHL could win its case. "To me the only grounds they can possibly use is that he is not going to play those years and this is somehow a cap circumvention," he said. "That would be their only argument because there is no limit on term in the CBA."

What I like about this article is that Barry is exactly right. There is no language in the CBA that specifically limits the length of a contract. He is also right in his characterization of the contract, that it contains several elements not before seen in one package. Last but not least, he is right about what the league's grounds are. Oh, another thing, he's right that it's their only argument.

I personally think it's the only argument they need.

Presumably, his clients' contracts are not circumventions of the CBA because his clients can plausibly be expected to play to the end of their contracts. Kovalchuk cannot plausibly be expected to play to the end of his contract.

Nine players, I keep reading, in the history of the league have played to 44. Nine out of thousands. That's much less than 0.9%.

If I negotiate a contract to pay you to get in a rocket ship and fly to the moon, despite the fact that the likelihood of you being able to do this is 0.9% (for the sake of argument), is this a valid contract? No. And it's not an enforceable one, either. I can't make you do something you have essentially zero chance of doing, nor can you sign a contract that commits you to doing something you have no reason to believe you will be able to do.