On tonight’s Insider Trading on TSN, Bob McKenzie offered up an interesting idea to mull over. He said he personally believes both the Leafs and William Nylander want to end this impasse with a deal, not a trade or a missed season.

McKenzie is quoting an unnamed agent, who is not involved in this situation (which isn’t very many of them, considering Pierre LeBrun says one third of the league has checked in with Toronto about trades.)

This unnamed agent’s idea is this:

A three-year bridge deal with an AAV of $5.33 million that is structured as: $3 million, $4 million and $7 million in salary. McKenzie describes this plan as more than the Leafs want to pay, and less than Nylander wants, which sounds perfect to me.

This structure gives Nylander the status amount of salary in year three he wants, as he is still an RFA at that time with arbitration rights. It is a discount off of his likely market rate however. When I looked at all the possible contract lengths they could agree on, this was the three year options:

Three Years

Expires in 2021

[Matt] Cane’s projected AAV: $6,302,581


If they have to settle on a bridge deal, three years might work for the Leafs. But just getting past 2020-2021 doesn’t guarantee labour certainty. The big negative for a three-year deal for the team is that Nylander is an RFA at expiry and yet the AAV is going to creep up to something close to what they’d be paying to buy UFA years. It’s not a beneficial compromise for the team unless they really force Nylander to a lower number on the AAV than the model forecasts.


If Nylander has good luck, or even just no bad luck, a three-year deal now followed by a seven-year deal could make him the maximum amount of money over his career, more even than if he starts with four years now. He would be 25 when the deal ends in 2021, and would have multiple seasons of results to draw on as an RFA with arbitration rights. Players and their agents don’t like to play poker against the gods of luck, however. One ill-timed injury and this scenario all goes up in smoke and the Leafs could have the arbitration advantage. He would also have to be very concerned at all the trade deadlines that would be sliding by, with the temptation for the Leafs to trade him.

The best you can say about this deal is that it’s better than all the other short-term options, but given the risks he’s taking on a bridge deal, he’s not going to want to give out discounts on the AAV.

This structure, which sets Nylander up to negotiate an extension of more than $7 million, sounds ideal.

One other note on contracts, Cap Friendly has dug into the cap situation for deals that have heavy signing bonuses in the current year:

You will note that in the second table, the one with the signing bonuses on the deal, the cap hit reduction in later years is much lower. I have (loudly) maintained that for the Leafs, this cap hit savings in subsequent years, less than $450,000 in the table one example closest to the above idea, is not significant for solving any cap problems the Leafs might have. It’s the difference between a league minimum backup and giving Garret Sparks a raise as an RFA with arbitration rights. It’s not important. For acquiring teams in a trade, with different situations and less ability to have cheap depth players, this might be meaningful.

One other reason Nylander might like this idea outlined above is exactly the difficulty  teams not the Leafs have in taking on a player whose cash salary is much greater than his cap hit. If Nylander took a deal like this with no signing bonus in year three, but that big cash salary, the Leafs would have much more trouble moving him if they suddenly go the idea to trade him away.

The stated reason for Kyle Dubas’ trip to Switzerland last month (wow, was it only last month?) was to reassure Nylander that they aren’t going to trade him in a year or so if he takes a short-term deal.

So, what do you think of this scheme?

Do you like this contract idea?

Can I mail him a pen?849