Wonder if the holdup is because of the league getting involved? All that bs media inquiry stuff. Only in Toronto.
Here's my thoughts on how this all went down:
* Leafs are interested in Tanev as a free agent. They talk to Dallas about his rights (as they may have done with teams of other UFAs they have interest in) and found out they can make the deal for almost nothing, so they do it.
* Tanev's agemt honestly tweets that he has had no talks with the Leafs.
* Some media, misinterpreting the rules for giving an eight-year deal, jump to the conclusion that the Leafs must have made the deal to give Tanev an eight year cap circumventing deal. After learning they're wrong on the 8-year thing, they still continue with the idea that the same sort of cap circumvention deal could be done with a 6 or 7 year deal. And many in media and amongst fans have simply bought into that story.
* As for the Seravalli tweet about the NHL monitoring possible cap circumvention deals, I think that was simply Seravalli asking the NHL about such cap circumventing deals and getting the same answer about monitoring such deals that he would have gotten six months or even six years ago. I don't think it was Seravalli reporting a statement being put out at this time by the NHL.
* Tanev and the Leafs have discussed a possible extension and Weekes believes the AAV is in the $5M area,
I'm not sure we know anything else. I've seen no reason to believe that both the long term contract and the $5M AAV are both true.
It's quite possible that the Leafs and Tanev have reached a deal to be announced later. It's possible that they are still talking. It's possible that they simply know where each other stand and they'll revisit it early into free agency, each knowing that the other could find a deal they like better.
As for the NHL monitoring these possible cap circumvention deals, you have to remember that the contract itself is not where the violation is occurring but rather it is how the deal is reached which is the violation. Basically, teams and agents are not supposed to make deals that include side agreements like a bigger deal down the road, the player agreeing to retire early before the deal is done, promising the player a front office job after their career, giving the player's spouse a job, etc..
Personallly, in the case of cap circumventing contracts, the NHL probably requires real evidence (emails, text messages, sworn statements by someone involved, etc.) there wsa some kind of actual agreement for the player to retire early or to fake an injury requiring them to be LTIRetired.