It has been 54 years since the Toronto Maple Leafs last won a Stanley Cup, but they certainly do have the personnel on hand to win multiple Stanley Cups if they make some adjustments to the team.
At the Trade Deadline, one major trade is made:
Toronto Maple Leafs acquire Derick Brassard, Drake Cagguila from the Arizona Coyotes for Jimmy Vesey, 3rd round pick '21.
The Maple Leafs get Brassard and Cagguila to bolster their depth for a deep playoff run.
The Toronto Maple Leafs end up losing in the Conference Finals to the Tampa Bay Lightning in 6 games.
Joe Thornton Retires after the 2020-21 season.
Toronto Maple Leafs lose Zach Hyman to the Seattle Kraken in the Expansion draft
Before the 2021 draft, two major trades are made:
Toronto Maple Leafs trade Travis Dermott, Alex Kerfoot, Ilya Mikheyev, 2nd round pick '21 to the Anaheim Ducks for Josh Manson, Max Jones.
The Anaheim Ducks acquire Josh Manson and Max Jones, the two players will provide some physicality and toughness to the team.
The Maple Leafs also trade Fredrik Andersen to the Detroit Red Wings for 2nd round pick '21 (from EDM), 2021 2nd round pick (from NYR).
The Maple Leafs get three picks in exchange for Fredrik Andersen, who the Maple Leafs were not likely to extend.
2021 Draft
29-Sasha Pastujov
41-Zachary Dean
54-Sean Behrens
The Toronto Maple Leafs draft two solid forward prospects in Sasha Pastujov, Zachary Dean, and a good defensive prospect in Sean Behrens.
Toronto Maple Leafs re-sign a few players:
Derick Brasard-1yr/1M per
Veini Vehvilainen-2 yrs/1.3M per
Toronto Maple Leafs sign a few players:
Petr Mrazek-4yrs/4.5M per
Brock McGinn-2yrs/2.2M per
The Toronto Maple Leafs win their division in the 2021-22 season and cruise to their first Stanley Cup in 66 years.
Before the 2022 draft, two trades are made:
Toronto Maple Leafs trade William Nylander to the Florida Panthers for Owen Tippett, Alexander Wennberg, 1st round pick '22.
The Maple Leafs get Owen Tippett and Alexander Wennberg, and a 1st for William Nylander.
Maple Leafs also trade Josh Manson to the New York Rangers for 3rd round pick '22.
The Maple Leafs get a pick back for Josh Manson, who wasn't going to get re-signed due to Toronto's cap situation.
At the 2022 draft, Toronto Maple Leafs trade picks 64, 3rd rd pick '23 to the Minnesota Wild for pick 43.
2022 Draft
20-Charlie Leddy
32-Jonathan Lekkerimaki
43-Topias Leinonen
Toronto Maple Leafs draft Charlie Leddy and Jonathan Lekkerimaki, two prospects who could be impact players a few years down the line.
Toronto Maple Leafs re-sign a few players:
Morgan Reilly-8 yrs/6.5M per
Owen Tippett-3yrs/2.8 million per
Alexander Wennberg-2yrs/2.5M per
Pierre Engvall-2 yrs/1.5M per
Toronto Maple Leafs sign Rodion Amirov to an entry-level contract
Toronto Maple Leafs re-sign All other RFAs
Toronto Maple Leafs sign Noel Acciari to a 3yrs deal worth 1.75M per season.
The Toronto Maple Leafs win back-to-back Stanley Cups for the first time since the 60s.
After the 2022-23 season, the Toronto Maple Leafs make one trade:
Toronto Maple Leafs trade Justin Holl, Sasha Pastujov, 2nd round pick '23 to Columbus Blue Jackets for Alexandre Texier, Andrew Peeke.
The Maple Leafs get Alexandre Texier and Andrew Peeke to bolster their depth on the team.
Toronto Maple Leafs re-sign a few players:
Alexandre Texier-3yrs/3.5M per
Rasmus Sandin-3yrs/3M per
Andrew Peeke-3yrs/2.75M per
Veini Vehvilainen-3yrs/2M per
Toronto Maple Leafs re-sign All other RFAs
By the 2023-24 season, the Maple Leafs have won two Stanley cups and are on the cusp of winning another.
2023-24 Toronto Maple Leafs
N.Robertson-A.Matthews-M.Marner
R.Amirov-J.Tavares-O.Tippett
A.Texier-Z.Dean-B.McGinn
P.Engvall-A.Wennberg-N.Acciari
M.Rielly-TJ.Brodie
J.Muzzin-T.Liljegren
R.Sandin-A.Peeke
P.Mrazek
V.Vehvilainen
Top Prospects: S.Behrens, C.Leddy, J.Lekkerimaki, T.Leinonen
The Toronto Maple Leafs have won back-to-back Stanley Cups and have a chance to three-peat if everything goes right in the 2023-24 season.
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