With the expansion draft approaching, every team will try to outsmart the system by figuring out a loophole to safeguard additional assets above and beyond the allotted limits for protecting players. Many fans also have their own theories on how to game the system.

In the Montreal Canadiens’ case, the question is what to do with unrestricted free agent forward Alexander Radulov. Does the team use one of the protection slots on him or leave him exposed? Can the Canadiens afford to lose on of last season’s most productive players, not to mention an unstoppable ball of unhinged enthusiasm?

Some speculation is floating out there that the Canadiens already have a secret deal with Radulov, to be announced once the expansion draft is over, and that he can be left unprotected as a result.

A clandestine background deal doesn’t count in the eyes of the National Hockey League. Either a player is under an approved NHL contract or he isn’t. There are no shades of grey. With only two options regarding contractual status, let’s discuss the available scenarios leading up to the expansion draft:

Protected and Signed

This scenario is the most straightforward. The Canadiens sign Radulov to a contract extension prior to the expansion draft, which is approved by the League, and then place him on their protected list.

Assuming the 7/3/1 protection model that the Canadiens will most likely go with, the seven forwards on the protection list will most likely be Max Pacioretty, Alex Galchenyuk, Brendan Gallagher, Phillip Danault, Andrew Shaw, and Radulov. The final protection spot would likely come down to Paul Byron, Tomas Plekanec, or Charles Hudon.

Unprotected and Unsigned

In this scenario, at the time of the expansion draft Radulov does not have an NHL approved contract and will be considered an unrestricted free agent. Vegas will be able to negotiate directly with him and his agent. Should the two sides come to an agreement and Vegas drafts Radulov, the Canadiens would fulfill their requirement for losing one player, and won’t risk any other player being drafted from their roster.

Some believe the Canadiens already have a verbal agreement in place with Radulov meaning that they can expose him and not be worried about losing him. The hole in this logic is that until the League approves the contract, it is not an officially accepted nor binding contract and Radulov is still technically an unrestricted free agent.

If anything, having a secret agreement in place with the Canadiens will actually benefit Radulov, as Vegas will know what the starting point for negotiations would be. The nascent market in Nevada might be very attractive to Radulov, as would playing with former teammate Vadim Shipachyov.

This entire secret arrangement scenario ultimately hinges on trust. How much do the Canadiens trust Radulov to not take more money to play elsewhere if such an offer from Vegas materialized? The Canadiens would need to hope that Radulov was serious when he said that he wanted to stay in Montreal, and in turn Radulov would need to be satisfied with the result of the negotiations that had taken place with the Canadiens. If there is even a shred of doubt about one party’s loyalty towards the other, then Radulov could be wearing a different jersey next season, regardless whatever was arranged behind the scenes.

Protected and Unsigned

Even if teams were allowed to protect UFAs, which they aren’t, this is very much the riskiest move the Canadiens could make. It would buy them more time to negotiate with the forward, and it would show commitment to come to an agreement as well. However this scenario would give Radulov all the negotiating power, and could cost the Canadiens a lot of money if Radulov decides to squeeze them.

Of course the biggest risk in this scenario is not coming to an agreement at all before July 1 and Radulov walking as a UFA. This would mean that the Canadiens used up a protection spot for nothing, and in addition the Habs would lose a player to the expansion draft, meaning they would lose two players from their roster in total.

Unprotected and Signed

This option makes the least sense. Signed and unprotected? Vegas will just pluck Radulov from the Canadiens and go on their merry way. Unless of course the contract Radulov signs with the Canadiens is well outside their price range, one that no team will want the burden of carrying, probably including the Canadiens.

File this scenario away under not going to happen.

So as you can see there is only one sure-thing scenario for the Canadiens when it comes to Radulov. If they want him for next season, the only way to secure his services it to sign him to an approved NHL contract and protect him. Every other scenario is fraught with varying degree of risk and uncertainty.

Listen to Andrew weekly on TSN 690 Radio Sundays at 8:05am on Habs Breakfast, part of Weekend Game Plan.