next ur gonna sign seguin right? why not sign every player from toronto on one year deals?

Oh you forgot Mcdavid to right? He also was from toronto

Let's say the Kings trade Doughty for Nylander and Liljegren (not enough for Doughty in my opinion). Why on earth would they throw in Toffoli for JVR who's a UFA?? That trade is hilarious

If I was a MTL fan, I'd be holding my breath too.

Only the Doughty piece is a low probability event. Hence the "subject to" disclaimer. I'm pretty certain LA would take that deal or something close to it for Doughty if he told them he wanted more $$$ than Karlsson and they don't come to terms this summer.

good luck signing matthews and marner

so lets say doughty does get traded to toronto for nylander and plus plus. how u gonna sign him? ur gonna have matthews asking 10mill plus. doughty will ask for 10 as well. u still gotta sign marner. and u have so many guys coming of elc's. if u keep jvr, ur gonna have to pay bank for him too. he's coming off a career high in goals. he's not gonna take less then 6-7 years and 6-7 mill.

I tried to explain the contract steps above, but it's a multi-step project. Given the degree of difficulty, I referred to it as "Threading the Needle".

I guess most commenters didn't read the entire post (it is long, I know). It's more confusing because I can't input multiple contracts for players. The premise is that Tavares would set the upper limit for the team, in the interest of building the right team. Stamkos and Hedman have done this down in TB, taking pretty major pay reductions to free up more cap space. They are in great shape long-term for it. The Hawks are a good example of setting the upper limit too high. They have been in cap hell for years since. Here's the breakdown of contracts:

Tavares signs for $10M/yr in 2018-19 on a one-year, then extends for $11M/yr starting 2019-20 on an 8-year deal. He could get $14M/yr to go play in VAN and put winning on the back burner during more of his prime years, sure. I see him picking a contending team today.

Doughty is similar to Karlsson. One more year on current contract, can start negotiating the new deal this summer. He has one more year at $7.0M in 2018-19. Matthews also has one more year and can negotiate his next contract this summer.

So, Matthews and Doughty sign identical one-year deals for $9M in 2019-20, subject to signing matching $11M/yr on 8-year deals starting in 2020-21.

Marner is not the same calibre as Matthews, Tavares, Doughty, so he gets different treatment. Marner signs something like $7M/yr on a 3-year deal that starts in 2019-20, which allows him to maximize his next contract by playing with Matthews and/or Tavares during those years and earning his way into a large contract in 2022 summer. By that summer, the NHL will be working with a $90M+ cap level, maybe even $95M.

JVR is out -- sign and trade (or just include his UFA rights) to LA in that deal. Nylander also moves and doesn't need a pay raise in TOR.

Kapanen, Dermott, etc. can all be managed. Younger, lesser players are OK with taking some slightly lesser salaries when their leaders do the same.

So firstly you gave the example of Hedman and Stamkos. Both did take a slight pay reduction. But look in the state and market they are playing in. The team they were playing on had proven something in the playoffs. they play in florida, which is sunshine state. the cost of living is much cheaper then anyplace in Canada. Taxes, media and an engaged, yet sensible fan base give them a good reason to take a slight discount. no market in canada can compete against that. its cold here, cost of living is expensive, taxes are high, and the media is crazy. that is a huge reason why they took a pay discount. any player in canada wont take that. and again tampa has proven something in the playoffs. they went on deep runs. toronto hasn't. despite the wealth of high draft picks, they haven't been on any deep run whatsoever.
secondly you mention 1 year deals. they dont exist anymore for ufa's in their prime. say toronto offers a 1 year deal to tavares, and he takes it, and get a career ending injury god forbid. he's done. he has no money coming in now. for security purposes and stability players in their prime dont take 1 year deals. if tavares was 38, sure he'd take a 1 year deal, but he's 28 entering his prime. he'll take top dollar and max term. if toronto comes in with 10mill for 1 year, st louis would say 11 mill for 7 years, or san jose, dallas, even new jersey could step in and offer more money and more term. so the idea of taking discounts in superstars doesn't exist anymore. ur offering a 1 year deal, while playing in canada, and not having proven anything in the playoffs, and you expect a top ufa to sign? u must be crazy. doughty was very clear in saying that he will take subban type money. the guys a super star and one of the best defensemen in the world. why would he take less then 10mill for 7 years? explain that logic to me? for a chance to win a cup with a team that still hasn't gotten past the first rd? he's a norris caliber defenseman. he'll make top dollar and max term. matthews u said will take an identical 9mill contract. according to his production, age, worth to the franchise, projected cap hit, what he has to deal with in toronto, taxes, weather, media, and what his counter parts make, he wont take anything less then 11mill. eichel is 10, mcdavid is 12.5, so matthews will be in between those 2 at max term.
marner is not the same caliber as matthews, but 7 to 7.5 seems reasonable for him. and as for the younger players u mentioned, yeah u can give them 2 year bridge deals if they still havent proven themselves, but after u gotta pay up.