Speculation: What was this Teams biggest mistake?

[Dekes For Days]

How come the leafs were the only ones to really suffer then lol?

They weren't, but they were impacted the most, since they were in a competitive phase and had just recently committed a big amount of the cap by the existing standards through that entire period of time.

 

[CDN24]

I think Tavares was, if not the biggest mistake, the mistake that set them on the path that led to many other mistakes and where we are now. It seems like decisions were made based on short term impact without any consideration of the long term consequences. While 2018 Tavares was a great catch, it was the wrong move. They had other needs, namely on the back end, way more important than a no 2 centre.

At centre they had Matthews who was clearly going to be no 1, and Kadri who was coming off 2 30G seasons as your no 2 on a great contract. The issue was there were no high end D-men available in 2018 and they rushed it by signing JT. This contributed to overpaying Matthews and Marner that then led to the annual sell off of depth guys to get under the Cap for the next year.

Could the JT signing have worked? Maybe if they had used either that great Kadri contract or Nylander to land that stud D via trade immediately. By holding on to the big 4 and Kadri as soon as summer 2019 they were in cap crunch mode which led to brutal trades like the Kadri for Barrie/Kerfoot, pay a 1st Jarvis to get out of Marleau, losing Hyman for nothing etc.

It's easy to say in hindsight that they should have avoided any big UFA moves until summer 2020. By then you young guys are extended long term for less than 11M each, Marleau has gone without having to give up a 1st and now you have the cap space to chase Pietroangelo. However, I suspect that had they some how avoided Tavares they may have made the mistake in 2019 UFA season on a D man like Tyler Myers who was UFA that year.

So way more than one wrong move to get where we are but it feels like the JT contract is what set all this in motion, every move since has been reactionary to address cap issues, or try to plug a glaring hole with a plug that is just a bit smaller than the hole.

 

[ACC1224]

How come the leafs were the only ones to really suffer then lol?

They were the only ones with the rookie GM learning on the fly.

 

[francis246]

Small nitpick, but Nylander played 22 games in 15/16, burning an ELC year.

Yes, you’re correct. I would have burned a year of Marner’s too. Even if they ended up sending him back to junior. I think it would have helped to prevent that Marner/Matthews comparison.

 

[notbias]

Yes, you’re correct. I would have burned a year of Marner’s too. Even if they ended up sending him back to junior. I think it would have helped to prevent that Marner/Matthews comparison.

It would have been nice if some of the ELCs sucked like MacKinnon on his... would have got some nice "discounts", instead, Nylander found his game just in time for a contract last year.

What you're saying though may have helped with this.

 

[ACC1224]

Yes, you’re correct. I would have burned a year of Marner’s too. Even if they ended up sending him back to junior. I think it would have helped to prevent that Marner/Matthews comparison.

Could have easily signed Marner before Matthews to take away that comparison.

 

[Nineteen67]

Yes, the reason Covid didn't help is because of having to face Columbus, not because they priced in cap increases to their salaries as every single contract negotiation does, and then the cap went stagnant.

Genius-level analysis.

Look at the return on Kadri, pre Covid. They were forced to take Barrie because they were up against it. With proper management Covid would have been a gift.

What no one could foresee is that the core are not good enough players to succeed in the playoffs.

 

[CDN24]

Because they signed all their big contracts right before covid lol

Other teams suffered too, but some suffered worse than others, not sure a team got it worse than the Leafs.

Tampa signed Kucherov and Point to extensions kicking in for 19-20 right before Covid. Avs extended Rantennan at the same time. I guess it cost them cups too

 

[Nineteen67]

Dubas admitted the mistake with the signings. I wonder if one day his fans will too?

 

[francis246]

Tampa signed Kucherov and Point to extensions kicking in for 19-20 right before Covid. Avs extended Rantennan at the same time. I guess it cost them cups too

I agree I don’t think Covid can be used as the overarching excuse. It was leafs managements decision to not pivot post covid that has caused them issues. Once the flat cap was initiated. I’m sorry but someone from the core 5 had to go. We didn’t take advantage of that. Personally I think in hindsight, Nylander maybe should have been traded for a stud dman because he probably had the value to get one back in 2021. I’m glad we’ve kept him now though cause he’s insanely good.

 

[notbias]

Look at the return on Kadri, pre Covid. They were forced to take Barrie because they were up against it. With proper management Covid would have been a gift.

What no one could foresee is that the core are not good enough players to succeed in the playoffs.

They were forced to take Barrie because Kadri stopped a trade for Brodie.

Kadri also is the reason he got traded...

 

[banks]

The Tavares signing hasn't worked out as planned. But I don't think that was the real problem. Any GM would have done the same. I think the bigger mistake was not dealing with the RFA contracts properly. They played hardball with Nylander, like they should have. But gave Marner and Matthews anything they wanted. Why? Those negotiations were botched in my opinion.

As for other errors, I can think of one big one. The goaltending. It's been mishandled since Freddy Andersen was here. The management never should have let the fans convince them that Freddy was the problem, he clearly wasn't. And if moving on was inevitable (and I agree it may have been) then they should have found a proper starter to take Andersen's place. I'm glad they didn't commit to Jack Campbell. But all they did instead was continue to misfire on the starter and backup roles. They're acting like the position doesn't matter, and the amount of pressure now on Woll is colossal.

 

[TMLBlueandWhite]

So many franchise crippling mistakes over the years.

By so many different people. From JFJ to Lou and back to the youth movement with Dubas again. Every end of the spectrum has been tried and failed.

Losers all of them.

It's mind boggling a team with the resources the Leafs have could be run so shoddily. Poor reflection on ownership for sure. If Tanenbaum's ok with all the losing then I guess he’s ok with being a loser.

A bad look for the fans who are paying for it all too if you ask me.

If you're still financially supporting this team you're part of the problem. Gratuitously compensating such gross incompetence a thread like this could be created. The saddest thing is that I expect it to reach several thousand responses given how many franchise crippling mistakes this team has made over the years.

There's more than one that could arguably lay claim to the honour of being the worst.

 

[notbias]

Tampa signed Kucherov and Point to extensions kicking in for 19-20 right before Covid. Avs extended Rantennan at the same time. I guess it cost them cups too

Every team signed high-end players during that time, but did any team sign as many as Toronto?

So far by your example, the answer is very clearly no, so thanks for helping with that.

 

[LeafGrief]

Somewhere along the line, the team became about the big guns, rather than the team as a whole. It's not really about one of them individually, but rather how as a group of four, the team revolves around them. Their ego's are of paramount importance, their wallets our biggest priority. It seems like the team's identity has become "our best players are better than your best players" and that's the be-all, end-all.

I think it stems back to the contract saga. Nylander holding out was a disaster, the JT contract set the bar high, and then Matthews and Marner both fought to cash in. Believing that these guys were talented enough to lead us to the promised land made paying them seem like a worthwhile gamble, but as a group they just can't get it done. From here, the organization let things spiral out of control, naming Tavares as Captain was a disaster that ensured a weak dressing room, and getting a butterball coach in Keefe meant even weaker leadership. A few years of this, kowtowing to the players despite their failures come playoffs, compounded into a team culture that's summarized as "we're still hot shit guys, we'll get 'em next year". Their egos match their paychecks, not their results.

If I had to pick one specific moment here, I'd say that the Tavares signing was the mistake. Partially because it put far too much of our cap structure into forwards, partially because it blew up our internal cap structure, and partially because it lead to him as our captain and his weak leadership has allowed the team culture to snowball. Marner is the biggest problem we have today, but I don't think he turns into this horrendous of a playoff dud with better leadership and a different salary cap narrative.

 

[GoonieFace]

Trading Lafferty, the beginning of the end

 

[Dugath]

I have to agree with what has been said, signing JT to 11m. This raised the internal pay scale and now for years the Leafs have been stuck trying to get bargain bin players to fill out the rest of the team, this simply does not work. They could probably got MM and AM to sign for a whole lot less considering what WN signed for at the time. Then this team would have been able to afford better players to fill out the rest of the lines. they are now stuck like this until JT's contract runs out and would be even better if they could trade MM leaving 20m+ to use on the rest of the team.

I am tired of this team trying to get cheap "talent" or old past their prime players, penny pinching all because 4 players have all the cap space.

 

[QJo]

The biggest mistake was trying to rush success instead of allowing the core of the team to develop.

If you're looking for 1 move which exemplifies this it would be signing JT. Since that caused a cascade of internal salary comps , which blew out the budget, cost us from keeping many good players we already had and didn't lead to winning.

But man there's lots of mistakes made all trying to force success instead of letting the good young core struggle. Trading too many pics, bad salary cap structure, letting the wrong players walk etc

I disagree about rushing success. I think as soon as you have your golden goose get them winning. Don't let them develop in the league on a basement team like Eichel. The time to leave a losing culture in the past is as soon as you can.

I'd say the biggest mistakes made were contract salary, term and flexibility, in the opposite order.

 

[freshwind]

I agree I don’t think Covid can be used as the overarching excuse. It was leafs managements decision to not pivot post covid that has caused them issues. Once the flat cap was initiated. I’m sorry but someone from the core 5 had to go. We didn’t take advantage of that. Personally I think in hindsight, Nylander maybe should have been traded for a stud dman because he probably had the value to get one back in 2021. I’m glad we’ve kept him now though cause he’s insanely good.

this bolded part to me is the real key to everything that has cascaded since ... if the cap was 100+mill today would there be as much arguing over contracts? maybe, maybe not .... i suspect there would be more 10+ players league wide as well

there was definitely an inherent risk in signing the "core" to those contracts but it was done with a certain cap projection in mind, when that went kaput they chose to continue to double down instead of adjusting, to me that decision has led us to we are today

we are where we are, and sadly with shanabang in charge i do not see any changes forthcoming ... maybe (fingers crossed) he ticks off pelley and is not renewed

maybe even worse than that is i will continue to follow the team, hope beyond hope, and at my age i guess i even look at a spring collapse as a good thing, means i am still on the right side of the grass lol

 

[ULF_55]

Random thoughts - in some cases seemed like a good idea at the time
Butterfly effect

Not allowing JFj to initiate the rebuild (results included moving a prospect keeper for a flash in the pan)
Hiring - Burke, drafted only North Americans on purpose (Cherry his advisor?) "I can do it quicker."
Hiring - Babcock, underlying issues known to players elsewhere (Let me creep you out.)
Hiring - Lamoriello, another past his BBD (Brodeur won their last Cup in 2003)
Signing - Marleau ... a good player but not the right fit and for too long
Going with a rookie GM
Getting Barrie in the Kadri trade
Going with a rookie coach
Matthews contract
...

 

[Shooter2x]

Due to how close most of our playoff series losses were, you can say Nylander on PP2 in the Habs series for the likes of Thornton and Simmonds has been one of our hugest mistakes.

Even just 1 power play point extra from Nylander on PP1 in that series could have changed that entire post-season.

At least the coach who organized that is gone.

 

[QJo]

Actually, I hate that our rookie president hired a rookie GM who hired a rookie coach to guide our most promising cup window that I can remember.

Shanahan (and everything else) looked really good until letting Lamoriello go. Every high profile option was coming to the Leafs, Shanahan, Babcock, Lamoriello, Tavares, Matthews. The sky was the limit.

Then Shanahan balked at losing promising young talent (Dubas) and changed the trajectory of our team. There's a straight line between the fear of losing Dubas before he was ready and signing RFAs to mega contracts and hiring the Marlies coach. All the same mentality, all 180° from the promise of 2016.

All of a sudden the optics changed from the 'place to be' to 'please don't go' and we've suffered that mentality since.

 

[tuckerintensity]

If I could change one thing post lockout, it's likely the trading of Nazem Kadri. That may sound weird, but that trade was so emotionally charged (and I was sick of Kadri too) and if we don't trade him. It's the biggest what if moment of the Shanahan era for me.

And maybe Kadri walks at the end of that, I wouldn't have signed him to the contract BT did, but until then he was on a pretty great contract and would've fit nicely into this roster in a lot of ways. He's the kind of player we've been kind of begging for since he left.

That or signing JT. As much as I think he's been good for most of his contract, he's the contract that is hurting us most.

 

[Peasy]

They were forced to take Barrie because Kadri stopped a trade for Brodie.

Kadri also is the reason he got traded...

They werent "forced" to take anyone...

 

[JEI]

Every team has missteps, some more than others.
What do you feel was the biggest mistake this team has made? (Limit your response to post lockout/salary cap introduction)

I can think of a bunch but not sure yet which I feel was the 'biggest'.

I feel like the slow to react has plagued the team since the JFJ days. Coming out of the lockout when they introduced the cap system the Leafs were slow to change with the movement towards more of a speed game. Had the chance to buy out of contracts (without penalty - a virtual clean slate), clear salary and if memory serves correct, JFJ took a wait and see approach. I think at the time they thought the game was going to revert back to the clutch and grab style, but they were wrong to invest/keep faith in the players they did.

Fast forward to more current times and I think even Dubas admitted to being slow to react to signing the contracts of Nylander/Marner/Matthews. Dubas even mentioned having to go through a various change of command to get things done which may have prevented other trades or moves from happening. Shanahan seems to be the one at the top of that snake head though - the reluctance to move off of any core players when he had the freedom to do so (now, locked into movement protection on these players). Tough to sit through when you see other teams making proactive changes vs. reactive ones.