Let go of the past, learn about cap life

This is a really good troll, honestly.
But if this is serious, I'll just say these few points.
Olesiak - Not worth Bozak, Gardiner and Marinicin NOR is he worth 5 million (Bad deal that would kill the Leafs long term)
Letang - Waste of a good Center in Kadri and a 1st, since Letang can't stay healthy no matter what and his career is more than likely coming to an end because of it
Defense is much weaker than it was before, given that Letang will get hurt and Gorges isn't an amazing defender who didn't want to come to Toronto in the first place.
Kaskisuo is not going to make the Leafs, they're going to work on Woll and Scott and have Sparks a possible backup in a year or so, if ever.
The offense is much weaker given we have NO center depth and Komarov feels more confident at wing.
All in all, good troll, bad team.

Honestly, it's not a troll. Any fan of the Leafs that wasn't emotionally attached to the Kadri/Bozak/JVR era would want this if it wasn't 50-50 whether the other teams would accept.
I knew this would seem radical, but that's just because it's unfamiliar. One way or another the Leafs won't be keeping Kadri/Bozak/JVR, so get ready to face cap life.

Oleksiak -- you will know his name, once you've actually stayed up past your bed time to watch the 6'7" hometown Toronto boy who can do it all.

You only get Letang for Kadri + Rychel + 1st because he's a little expensive for being a little old and often injured. It also depends on him waiving his NMC. You're also hoping the Penguins want Rychel's grit after they already signed Reaves.

Gardiner scores, but requires a babysitter at all times either because he's cheating to inflate his numbers, or because he's stupid defensively. If he's in your top 4, your team will never be a contender.

The D is much better, and the Leafs' star players will spend more time with the puck instead of coming down below the circles to retrieve it themselves.

You got lucky with McElhinney last year, Sparks is ready for NHL time. If you delay, you'll end up losing Sparks and Kaskisuo for nothing at age 27.

The bad contracts for Gorges and Moulson wrap up before the cap space is really needed.
Center depth is spent and redistributed, giving prospects opportunities to steal a job and get the most assets out of the available pool. Under the cap, you need to trade redundant depth and keep just what you can actually use. Then you race against time to find a prospect who will be ready to fill a spot before a hole opens up.
You don't even recognize Alex Nylander, and I know you would argue William Nylander is worth 4 1st round picks as a starting point.

edit:
I moved Marleau to C, and Letang to RD where they belong.

Check out the 2019-2020 season after this big set of longshot trades

$37 million of cap space, with cap at $75 million.
8 players under contract, 15 to go

must sign 7 RFAs Matthews, Marner, W Nylander, A Nylander, Kapanen, Carrick, Marchenko -- could be $40 million easy
need 8 bodies to reach the standard 23 man roster
league average is $3 million/player, minimum is about $1 million. Assuming with the top 6 and top 4 secured, you fill out the roster with $1 million prospects or UFAs
That's a $86 million payroll just 2 years from now. That's why you have to trade all your favourite players, it's not because other teams are thirsty for them.

You have to wait until 2020-2021 until Marleau and Martin are gone, freeing up $8.75 million

This is the first time Leafs fans are being introduced to the realities of the salary cap era, they need to adjust their expectations

You know what you're talking about, and I respect that, but I fail to see how we need to be introduced so quickly.

You traded away JVR to get two UFAs with bad contracts to equal us getting A Nylander (which would never happen) and then turned Bozak over as part of a package deal for a young Dman so that we won't be hit with cap problems in the future, right? But why do we need to trade them before THEIR contracts expire at the end of the year? I'm under the impression that, barring a trade using JVR or Bozak to shore up the D on the right side, Leaf Management is going to run with them for the season and make the hard decisions next year, and as a Leaf fan who's talked to many Leaf fans, we know they'll more than likely be gone at the end of the year and it's hard to accept but it's for the future. I just don't see why we would jump the gun and trade them for things we don't need and weaken the team now when we're in the unique window we're in.

For the Buffalo trade, you're suggesting that the Leafs make a divisional trade, and it's not a very good or understandable trade. The Sabres are more than likely going to hang onto Gorges for the rest of the year and let him walk later, and possibly buyout Moulson if they need to at the end of the year. The idea that they'd need to trade both of them so badly they'd include possibly their best prospect and weaken *their* future pipeline is not a feasible one. The only way I see them moving a prospect to get rid of a bad contract is only if they move a less valuable prospect and a pick, and keep Nylander.
Yes, in your trade scenario, JVR is headed their way and they get a pretty solid LW who can put up good points, but that's when it doesn't make sense for the Leafs to make the trade, because aside from getting Nylander, who might do better under Babcock and playing with his brother, isn't tracking to be an absolute all-star in my opinion, and if he does become that with the Leafs, he'll cost more than JVR would have with the team and put the other contracts in jeopardy. In the end, that's not where the Leafs need help, and given Buffalo probably passes on the trade so that they can keep Nylander and have an even stronger future, and the only way I see them trading him is for defensive help.

The Oleksiak trade is something I can't even believe I have to clear up. I watched Oleksiak play junior and thought he was awesome cause he was so big. Now I look at a 6'7 defenseman, who even on a depleted defensive team like the Dallas Stars still has yet to play a full season. I look at his stats and I really see why. Yes, he's a big guy, but that's really about it. He's really not that great, and I refer you to go to look at hockey-reference.com to look at all the stats, and at the bottom you'll see players who share the same statistic trends as him, and I'll give you a preview, players like Trotman, Reese, Olsen, Janik and Cote share comparables with him and do you know what they all have in common? They're all fringe NHLers/failed NHLers. So no, I'm not trading my offensive defenseman who may struggle in his own zone some nights, plus my best faceoff guy AND one of our depth defensemen for a guy who probably won't make that big of an impact, and NO I'm not going to pay him 5 million dollars. I wouldn't mind Oleksiak on the team, he might do well under Babcock, but at the end of the day he's not worth what you say he's worth, and I don't think he ever will be.

Now, when it comes to the Kadri for Letang trade, you didn't address the injury and health issues plaguing Letang, and the jeopardy of his career. You also say that the Leafs can't keep Kadri, yet they signed him to this deal last year, giving him the money and term they did because he's practically a steal at that price and more than that he's locked up for a long time. Yes, it's possible in a few years that they could trade him, but with the unique position we're in right now and with the knowledge he just came off his first 30 goal season, I don't find it smart to trade him for an injury riddled player.
And also, if you're preparing the team for the hurt of a salary cap, why acquire a player who's worth 3 million more than Kadri is, and can't stay healthy?

After looking at the cap situation and running over different scenarios, granted the Leafs don't overspend on key players, then the team will have more than enough room to keep Kadri AND the core they've built. I see your little cap situation you created, but it's for nothing ultimately. If you look at the Leafs CURRENT roster and take it to 2019/2020, you'll see the team has players under contract that can be called up to fill holes (Bracco, Brooks, Grundstrom, Nielsen, Dermott and Liljegren, not to mention possibles like Korshkov and Woll) and cap space to sign Matthews, Marner, Nylander and Kapanen, plus some depth players, while also keeping players like Kadri, Brown, Hyman, Martin and Marleau, although you're tight to the cap. Given the way Marleau's contract was made, with him only being paid 1.25 million after the signing bonus in the final season, don't be surprised if he's turned over in the summer that year to a team that needs cheap help, which gives you 6.25 million more in cap space to sign some of these contracts to higher salaries or ensure you can bring the team back in the offseason. The team is fine right now.

You made all these trades to make the fans prepared, but we don't need to be. The management has already prepared the team to shed cap weight when it needs to.
JVR and Bozak expire after this season. Barring a trade, they'll stay with the team and leave in the offseason.
Gardiner expires before the 2019/2020 season, freeing up cap for them to sign some core contracts, and they have defensive depth in the prospects to replace him easily.
The team is fine as it is, except for the need of defensive help, which we'll more than likely tackle via a trade using JVR or Bozak or maybe even both, and granted it's a solid RHD coming back, then I'll be fine with that and the cap will be to.