No

explain why

You are trading virtually every prospect we have in the pipeline. Kerfoot is worth way more than a 5th round pick (why is he so undervalued by leaf fans?)
Laine is not something we need at all. While Forsberg would be great to have, he is a nice to have, not needed. And certainly not for the cost. Ekholm isn't needed nearly as much as people thing he is. The Leafs need a big body to play around 13-15 mins a night on that LD 6th d spot.

I like Jenner. He is literally the only asset you have acquired that the leafs could use.

Because the Leafs aren't the Penguins.

There's no need to gut the future to take 1 shot at the cup.

It would be two shots tbh, possibly more with the core locked up for 4 more years.

Kerfoot is under valued because he is over paid. Its a cap-dump. Leafs need a top 6 winger. Although what I acquired is a bit over the top, the Leafs could use 3 out of 4 of the skaters, plus Saros.

One of Forsberg or Laine would have to go next season (likely Laine).

Ekholm would be taken by Seattle.

There the team gets way worse the very next season.

Without a single decent prospect or high pick to fill in any gaps with cheap young talent any time soon.

That team would be in full rebuild within a few years.

Money would be off the books. You could flip Laine's RFA rights to re-tool the pipeline, or have him be offer sheeted (which would be rare). Ekholm would fall to Seattle, but the Leafs would have a ton of cap space, and they will likely sign a 1B goalie to platoon with Campbell. Leafs would be competitive for another 4 years through this plan, significantly worse is a stretch because they would still be better next year with this, then they are at this very moment. Sometimes you have to go all in to accomplish the goal.

Yeah, this plan probably works in NHL21.

"Sometimes you have to go all in to accomplish the goal" this applies when teams best players are approx. 30 yo (my Pens example). Not when the best players are 24 yo or under.

$$ off the books also means talent off the books. It also means overpaying aging UFAs to fill holes.

Just curious what your definition of "a ton of cap space" is? Under your scenario, with Ekholm picked up in the expansion draft, you have just over 11 million to fill 8-9 roster spots. No Laine, no Hyman, no starting goalie, almost half your roster bargain basement pick ups to be cap compliant, and no top end prospects or high round draft picks to fill your roster with cheap, high end talent. Teams will not over pay for Laine knowing the team is backed into a corner. These moves are the very definition of a 1 shot deal, after this year it will be ugly.

Leafs haven't won in 54 years. This is the season to go all in. Sellers market, trade bait won't be valued as much as recent years. Not saying both Laine and Forsberg will be leafs, but Dubas is rumoured to be playing all of his cards this deadline. We will see. Leafs won't win with this current team, they need to be Tampa-level to be true cup contenders/favourites.

With Phil Kessel's retention off the books, Leafs will have $13949384 in cap space (with Ekholm being drafted by Seattle). That will be used for Hyman, a 1B goalie, a bottom pair, and a fourth line. These deals don't set the team up for success in three years, but make them true contenders for 2021 and 2022.

All-in has literally never meant trading your top 6 prospects, and top 5 draft picks over the next 2 years on top of a few half decent roster players.

But your right, Dubas said he wants to make a deal, so this is probably what he meant.

Trades with 9 or 10 pieces involved are so common, one should be happening any minute now, it's pretty well a daily occurrence.

Kessel is not off the books next year. He still has a year left after this current one.