As ridiculous as this will all sounds:

2018:
Cup winners - Tampa Bay Lightning
Lottery winners - Buffalo Sabres
First Pick - Rasmus Dahlin
Tavares Saga- Resigns 10.5Mx8yrs

2019:
Bettman announces Seattle officially gets a team
Cup Winners - Winnipeg Jets
Lottery winners - Montreal Canadiens
First Overall - Quinton Hughes
Seattle names Team Seattle Steelheads

2020:
Cup Winners - Toronto Maple Leafs
Lottery Winners - New York Rangers
First Overall - Alexis Lafrireinerie
Carolina announces move to Hamilton
Hamilton is called Hamilton Bulldogs and takes over AHL team

2021:
Cup Winner - Edmonton Oilers
Florida announces move to Quebec
Arizona Moves to Houston
Quebec Nordiques are reborn
Houston Aeros are born

2022 4 divisons with VERY optimistic division standings

Gretzky:
Boston
Philadelphia
New York Islanders
Washington *
Buffalo
Pittsburgh
New Jersey
New York Rangers

Orr:
Toronto Maple Leafs
Tampa Bay Lightning
Hamilton Bulldogs
Columbus Blue Jackets **
Ottawa Senators
Montreal Canadiens
Quebec Nordiques
Detroit Red Wings

Lemieux:
Winnipeg
St Louis
Colorado
Nashville *
Dallas
Houston
Minnesota
Chicago

Howe:
Edmonton
Vegas
Anaheim
Vancouver**
Los Angelas
Calgary
Seattle
San Jose

Don't have much time at the moment, will make one soon ... but 3 teams move in 2 seasons?

Thank you for this exercise. It's a lot to think about, so I don't mean to nit-pick, but I'm assuming this was done in the hopes of inducing discussion:

1) I think I've assumed all year that the Sabres would turn this around (not completely, of course) and finish where they usually do (with the exception of the tank years): smack dab in the middle of teams that missed the playoffs. Not good enough to be in the chase, but not bad enough to have a real shot at the lottery. The idea of getting Dahlin honestly hadn't really sunk in until now and I think I just pee'd a little. Though, to be honest, we all know the Sabres can't win a lottery. So it'll be Edmonton.

2) Hamilton won't get a franchise. While it's true that the Toronto area can almost certainly handle a second franchise in that close a proximity, the Sabres probably cannot. The Sabres are a small market team, and a lot of that market bleeds into Canada and fan run-off from folks for whom Toronto is just a little too far out of the way, too expensive, or tickets are just too hard to get your hands on. At the same time, the NHL can't let the Sabres franchise sink. Buffalo has one of the strongest pro hockey fan bases in the states, and ownership is making a lot of investments around the city and related to the sport of hockey in general. While Hamilton would be a viable market, I think it would be at the expense of the Sabres, and I don't think the league will have any interest in letting that happen.

3) I would flip Buffalo and Columbus in the divisions. The Sabres/Leafs rivalry shouldn't be interrupted, especially with the careers of Matthews and Eichel just beginning. Trust me, that's going to be an interesting development (heated rivals for clubs, teammates for country). Plus Buffalo fits in more with the Canadian cities: we love Labatt and view the Hip as gods too!

2018:
Cup: Washington
#1 pick: FLA selects - Rasmus Dahlin
JT re-signs
2019:
Cup: Edmonton
Doughty, Karlsson, Seguin, and OEL all re-sign
#1 pick - MTL selects - Jack Hughes (are he and Quinton Hughes the same guy?)
2020:
Cup: Edmonton
Seattle Pirates enter the NHL
#1 pick - MTL selects - Alexis Lafreniere
2021:
Cup: Edmonton
#1 pick - VGK selects - No idea
2022:
Cup: Toronto
#1 pick - FLA selects - No idea

confused on why you put Tampa in the orr division with all the canadian teams and take Boston out of it. You know where Tampa is located right?

Well the NHL in all their wisdom did it with their last alignment. Why weren't the two Florida teams aligned with the more southerly US teams,,,,,Carolina, Washington and Philly, and the cosy NY hub of three teams.
Columbus and Pittsburg are much closer to Detroit, Buffalo, Boston and at the three Canadian teams.

2018
Stanley Cup Winner: St. Louis Blues
Lottery Winner/Selection: Arizona Coyotes/Rasmus Dahlin

2019
Stanley Cup Winner: Winnipeg Jets
Lottery Winner/Selection: Detroit Red Wings/Tobias Bjornfot

2020
Stanley Cup Winner: Toronto Maple Leafs
Lottery Winner/Selection: Seattle/Alexis Lafreniere

2021
Stanley Cup Winner: Philadelphia Flyers

Other notes: KHL and NHL reach transfer agreement, resulting in drafted player rights no longer in perpetuity.

I mean based off of recent decisions it doesnt seem like the NHL is ran by the most intelligent people

Montreal is not a lottery team next year. Unless Bergevin becomes an idiot.

I find it a little ridiculous you guys are trying to predict who will go 1st overall next year and you don't even know the difference between Quinton and Jack.

Quinton Hughes is a defenseman projected to go in the top ten of the 2018 NHL draft. He played for USA at the WJC.

Jack Hughes is Quinton's younger brother, he is a forward who may possibly go 1st overall in the 2019 NHL draft.

Flyers fans an Habs fans ...

Care to elaborate? Not like the team has an young core and stacked prospects in the pipeline and cash to spend in those years. Here is my projected lineup in 2020 with no UFA signings:

Giroux - Couturier - Konecny
Lindblom - Patrick - Voracek
Rubstov - Frost - Allison
Laughton - Vorobyov - DRAFT Pick

Provorov - Gostisbehere
Sanheim - Myers
Hagg/Morin/UFA - Hagg/Morin/UFA

Hart
Sandstrom
Ustimenko

Ok, you're right ... maybe in 2021 the Flyers could be a contender.

2018:
Stanley Cup Winner: Tampa Bay Lightning
Stanley Cup Finalist: Nashville Predators
Eastern Conference Finalist: Columbus Blue Jackets
Western Conference Finalist: Winnipeg Jets

2019:
Stanley Cup Winner: Winnipeg Jets
Stanley Cup Finalist: Boston Bruins
Eastern Conference Finalist: Tampa Bay Lightning
Western Conference Finalist: Anaheim Ducks

2020:
Stanley Cup Winner: Tampa Bay Lightning
Stanley Cup Finalist: Winnipeg Jets
Eastern Conference Finalist: Toronto Maple Leafs
Western Conference Finalist: Colorado Avalanche

2021:
Stanley Cup Winner: Tampa Bay Lightning
Stanley Cup Finalist: Nashville Predators
Eastern Conference Finalist: Toronto Maple Leafs
Western Conference Finalist: Calgary Flames

2022:
Stanley Cup Winner: Winnipeg Jets
Stanley Cup Finalist: Columbus Blue Jackets
Eastern Conference Finalist: Boston Bruins
Western Conference Finalist: Colorado Avalanche

Wtf is this

2 winners in 5 years is a bit ridiculous

it could happen, though not Tampa and Winnipeg IMO.

the league is becoming too competitive

The NHL has a long history of having dominant dynasty franchises; even in very recent memory (or even currently).

The league is becoming very competitive now a days. I can see a team like Tampa taking it home 2 out of the 5 years, but forsake very difficult for 3 as well as have the other years having the same winner as well. With Winnipeg, Edmonton, Nashville, Toronto and Columbus all on the rise, I can't see 2 winners in 5 years.

Realize the NHL just had back-to-back champions and only 3 winners in the past 6 years.
There's always teams "on the rise", but all to various levels and no way of knowing if any will rise "to the top".

that team also had 2 generational talents lol

I'm not saying i think it will happen, i'm just saying that there's always a chance. Though maybe Tampa Bay and Edmonton, or Toronto and Edmonton. Or even something like Nashville and Tampa Bay. You have to remember that we saw two cup winners in four years not too long ago (2012 - 2015). There's nothing crazy about two winners in five years.

yeah, we know. Tampa and Winnipeg? I doubt it. But other teams maybe ... Tampa and Edmonton?

This isn't the NBA. 2 teams in five years is a little extreme.

The league is growing in parity ever year.