Toronto Bay Maple Lightning

Stralman over Zaitsev.

Can you get Maple Lightning from a tree? The Lightning Leafs would have been a better name.

No

Okay... name wasn't the point of the post...

Fuji over Golden delicious.

Stralman over Zaitsev makes it an even 10/10 split.

Winesap over both.

Ya def Stralman over Zaitsev

Why would Nylander play center and Tavares play wing? And why is Raddysh there instead of Erne? Why is Vasilevskiy the backup when he's almost certainly the better goalie? And why Zaitsev instead of Stralman?

Matthews should be kept away from Kucherov, since both of them are offensive players who need someone defensively responsible.

I think:

Gourde-Tavares-Kucherov
Palat-Matthews-Marner
Hyman-Point-Nylander
Erne-Stamkos-Kapanen
Cirelli-Johnsson

Hedman-Reily
McDonagh-Stralman
Sergachev-Dermott
Carrick-

Vasilevskiy
Anderson

That way you have a 23-man roster. I replaced Kadri with Hyman mainly for cap reasons, but also because Kadri's not a winger and Hyman better serves that role. That creates an additional $2.25m in cap space, which is used to get Carrick ($1.3m), Cirelli ($728k), and Johnsson ($787k). I also switched Zaitsev for Stralman, moved Vasilevskiy to starter, and replaced Raddysh (who isn't NHL-ready yet) with Erne.

Gourde is mainly a space-maker, Tavares is elite offensively and somewhat defensively responsible, and Kucherov is one of the best wingers in the League if someone can play defense for him. Palat provides the defensive responsibility for Marner and Matthews. Hyman is a space-maker, Point provides two-way Selke-worthy play, and Nylander's a great offensive winger to compliment the line. Erne's a space-maker who provides a physical presence and occasionally scores, Stamkos is one of the best playmakers in the League, and hopefully Kapanen would grow into his role (otherwise, Stamkos can shoot the puck too, even though his 60 goal scoring days are long gone). Hedman is one of the best defensemen in the League both offensively and defensively, and provides responsibility for Reily's offensive skills. McDonagh and Stralman is a great shutdown pair that worked quite well during the playoffs. Sergachev is a great offensive defenseman, and Dermott is a decent two-way defenseman. That third pair would score occasionally and be able to play without being a liability.

If you organize it like that, I'd be shocked to see the Cup go anywhere else (obviously this team doesn't exist, though).