Toronto won't want to sign a four -year deal on Matthews. That's where the offer sheet comes in if he wants out. They match, and he goes to free agency in his prime.
Long deals are much better for the player. They get their contracts index-regulated as the cap goes up, right?. An old contract on a cap hit of, say 8 mill, goes up with the cap, so when the cap has climbed 30% thats actually 8*1.3 in salary. It does still count as "only" 8 mill in cap-hit. So a bigger star will always ask for as long a contract as possible, and the teams will really want to give them long contracts. A big star signing a shorter contract is odd.
When you calculate how much picks you give, there is a trick against shorter terms if I've understood this right. So short term don't lower the price. Not at all.
So you end up offering a whole lot of picks, while signing a player to a contract he will end up getting less money on.
Bad plan.
Future picks is so easy to undervalue. Just go read about how the Flames fans felt about not holding their first rounder this year if you don't believe me... They were scared to death Islanders should win the lottery with their pick. It was still suddenly a lot even if they didn't win.
So, Rinaldo to Nashville, Duclair to CBJ. Anything else fun?