What has been the Leafs biggest mistake?

[meefer]

With the Cup now decided, I've been trying to brush off some of the anger over the Leafs abysmal performance against Montreal. It was so defeating. But trying to make sense of it has not been an easy task. I see elite talent, I like much in the supporting cast, I'm not anti-Keefe but realize he can be better, Dubas got schooled in contract negotiations, thought we got ahead of ourselves based on the 16/17 season - more because of the regular season than the playoffs against Washington - and the resulting moves to hold onto JVR and Bozak and moving draft picks for uneventful rentals, the Babcock era, and for me, the number 1 disappointment I've identified is: terrible drafting.

Since the 2010 draft, the Leafs have had a combined 87 draft picks. Including: Brooks, Liljegren and Sandin, the Leafs currently have 9 players on the team. 6 of 87 players. Those drafted by the Leafs but are now playing elsewhere...not really an all-star cast. 6/87, two of them being Dermott and Engvall. Rielly, Nylander, Marner and Matthews, that's it. And, I can live with Dermott and Engvall. But, nothing else, nada. Not another 2nd or 3rd liner, and 2nd pairing Dman, a backup G, nothing. I have no idea if this is a league average type of success rate, but I can't imagine it makes building a competitive team easy (Vegas not withstanding).

Any thoughts, add if you've got something else. This isn't a restrictive list, I'm still trying to figure it all out.

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[Bomber0104]

Add poll option: Promoting Kyle Dubas to GM

 

[Canadian Finn]

getting rid of Babcock. (by caving into the children)

 

[forecheck]

Letting LOU go and hiring a Rook.

 

[meefer]

Add poll option: Promoting Kyle Dubas to GM

I'd do so, but I can't find a way? Any suggestions?

 

[A1LeafNation]

Drafting better could have solved a lot of problems.

 

[ACC1224]

Missing - hiring a rookie president who hires a rookie GM who hires a rookie coach.

 

[LeafsFan89]

Unpopular opinion - signing JT. Not because of the player (I love JT), but because of all the implications that followed.

 

[Koolboss]

Signing of JT well lets just say Dubas

 

[Aus34Matt]

Missing - hiring a rookie president who hires a rookie GM who hires a rookie coach.

This is so true. The best option is missing in this poll

 

[OVO16]

Unpopular opinion - signing JT. Not because of the player (I love JT), but because of all the implications that followed.

Was just gonna say this.

I have nothing against Tavares. He's a fine player and person....but him signing just handicapped us out so much financially that's its been extremely tough to put the other pieces around a cup-winning team.

 

[AvroArrow]

Hiring Dubas as the GM. Or the timing of it. If Lou stayed 1 more year just to handle the extensions and THEN Dubas came in, we'd be fine.

 

[Throw More Waffles]

I picked Dubas/Contracts.

But more specifically, I knew the precise moment where Dubas caved to Nylander that our fate was sealed and our promising young core was ruined.

Pastrnak paced for 38 goals/77 points his final elc year. Nylander 20 goals/60 points. To cave to Nylander and give him the Pastrnak contract (plus cap inflation, WAY more in signing bonuses, WAY more front-loaded, and 1 more ufa year). A contract that player-friendly was a sign of things to come. He was dramatically overpaid when compared to direct comparables. I KNEW that the same would happen fo the others.

We only say this contract looks good now when comparing it to Dubas's other unprecedented dramatic overpayments.

 

[Racer88]

You better add promoting Dubas to GM because that covers most of the other options
Just slightly behind promoting Dubas is signing Tavares

 

[Racer88]

Missing - hiring a rookie president who hires a rookie GM who hires a rookie coach.

On this we agree 100%

 

[francis246]

I’m going to go with the Hiring of Keefe. I’m not a Dubas fan but he did a decent job this year. I just think a veteran coach is what this team needs

 

[Jimmy Firecracker]

All of the above, but I voted for the constant moving of picks for rentals and never trading upcoming UFAs for assets. This team is unfortunately going to go into the “what not to do” category for rebuilds.

 

[Eternal Leaf]

The biggest mistake has been their salary cap management and how stubborn Dubas is about it.

One of the worst things a GM can do is assume things.

Dubas assumed the core four would get better AND the cap would continue to rise as projected. I can't blame him for the flat cap but he absolutely shouldn't have blindly signed the core four based on assumed production.

So many things can go wrong when you assume things as a GM and that's exactly what has happened.

Matthews was an 80-90 point player when he signed. Why is he getting a deal close to Mcdavid's and only signing for five years?

Marner had a single season of 94 points and signed to a ridiculous overpayment. In what world is a player like that worth 11 million for six years? It's not even for eight years meaning Marner wanted even more?!

Not a single player in the core three (Nylander, Matthews, and Marner) was signed to a team-friendly deal. They essentially got what they wanted. The Tavares deal was always going to be overpaid as a UFA, but that signing looks bad because of the other three getting overpaid at the time of their signings.

This is not even hindsight. A lot of people complained about the signings at the time they were signed. These were overpayments pre-covid and massive overpayments post-covid.

Just terrible and I think it's going to bury Dubas + Shanahan because they refuse to fix it by removing Marner. Ideally, you remove Tavares but that's not happening.

 

[Buds17]

Not yet winning a playoff round. Failure to do so has led to questions and doubts about cap management (mismanagement?) and trading futures for present help/retaining own rentals.

 

[rumman]

I'd do so, but I can't find a way? Any suggestions?

Add hiring Shanahan while your at it, he’s the architect of this fiasco.

 

[ShaneFalco]

Salary negotiations, especially MM's

 

[Budz]

Unpopular opinion - signing JT. Not because of the player (I love JT), but because of all the implications that followed.

I came to post the exact same thing.
I love JT - but this was the error.

 

[rumman]

Missing - hiring a rookie president who hires a rookie GM who hires a rookie coach.

Winner winner chicken dinner.

 

[Throw More Waffles]

The biggest mistake has been their salary cap management and how stubborn Dubas is about it.

One of the worst things a GM can do is assume things.

Dubas assumed the core four would get better AND the cap would continue to rise as projected. I can't blame him for the flat cap but he absolutely shouldn't have blindly signed the core four based on assumed production.

So many things can go wrong when you assume things as a GM and that's exactly what has happened.

Matthews was an 80-90 point player when he signed. Why is he getting a deal close to Mcdavid's and only signing for five years?

Marner had a single season of 94 points and signed to a ridiculous overpayment. In what world is a player like that worth 11 million for six years? It's not even for eight years meaning Marner wanted even more?!

Not a single player in the core three (Nylander, Matthews, and Marner) was signed to a team-friendly deal. They essentially got what they wanted. The Tavares deal was always going to be overpaid as a UFA, but that signing looks bad because of the other three getting overpaid at the time of their signings.

This is not even hindsight. A lot of people complained about the signings at the time they were signed. These were overpayments pre-covid and massive overpayments post-covid.

Just terrible and I think it's going to bury Dubas + Shanahan because they refuse to fix it by removing Marner. Ideally, you remove Tavares but that's not happening.

I'm willing to bet that on July 1st, 2018, Dubas essentially promised that signing Tavares wouldn't result in losing any of the core 3. He's essentially put his career on it, and a flat cap isn't a get out of jail free card for him. He can't move any of the core 3. His job is on the line.

 

[gabeliscious]

The biggest mistake in my opinion was not locking up Matthews, Marner, and Nylander when they had a year left on their RFA contracts and choosing to wait.

It was pretty obvious that all 3 were elite young stars. There was no reason to wait. Locking the 3 of them up would have been as safe a bet as you can make in pro sports. I think if they would have signed them a year earlier they probably at a minimum would have locked them all up for 8 years and would have been considerably cheaper. I think we would have saved a good $5 million in cap space if they would have done that.

The trickle down effect would have also set a salary structure in place meaning other players would just expect to make less. As an example, if Nylander was locked up at $5.5 x 8 years, Hyman would not be sniffing $5 million right now.