Rebuild | Measuring Ours Against the Precedents

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conFABulator

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Apr 11, 2021
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I have been thinking about this for a few years in a row now, right around this time of year for some reason. The thought has been – what does it take to rebuild a franchise to be a Stanley Cup champion, more to the point is are the Leafs on their way there or have they missed a window? Has a ship sailed?

Obviously, we don’t know the answer because this team and franchise still have a chance. They are a good team, with young and improving players, and organizational depth and they seem to be able to manage the cap as well as anyone.

In an effort to see what our future might look like I am looking to the past, specifically the past of recent cup winners and current contenders. I am not at all sure that this is a good way to be looking at this and I am also not sure that my analysis and data points are accurate as there is some subjectivity required. So please, jump in with your points and counterpoints, I am hoping this post is the beginning of a good discussion and it is not intended to be conclusive in any way.

METHODOLOGY

I looked at the five most recent Stanley Cup winners (which is actually only four different teams because Tampa has won twice…so far) and three obvious contenders this year (again, not including Tampa because they are part of the first group). These seven teams are:
  • Tampa Bay
  • St. Louis
  • Washington
  • Pittsburgh
  • Colorado
  • Carolina
  • Florida
I then looked for commonalities among them that we could use as a baseline to gather and analyze data. The commonality I discovered was that each of these teams had “bottomed out” and drafted high for a few years and then eventually went on to win a cup with the drafted core.

  • Tampa Bay. They hit rock bottom around 2008 and then drafted Stamkos first overall. They then followed that up over the next few years with Hedman (#2 overall), Kucherov (2nd Round), and Vasilevsky (19th overall). I think it is reasonable to say that their rebuild started with the Stamkos draft.
  • St. Louis. This one is a bit of an outlier in that they never really “bottomed out and drafted a star” the way the others did, but I think it is reasonable to say that drafting Pietrangelo was the beginning of a long road to a cup for them. He was drafted 4th overall in 2008 and that was one of the highest picks the Blues had. You could argue that Erik Johnson at 1st overall two years earlier was the beginning of their rebuild, but Johnson was not really a big part of their climb. I went with Pietrangelo and this started the rebuild clock two years later for this analysis I suppose. They did follow up the 2008 draft by taking Tarasenko and Schwartz both in the first round in 2010.
  • Washington. This one is obvious. They drafted Ovechkin (1st) and Mike Green (29th) in the first round in 2004 and over the next few years, they added Backstrom, Varlyamov and Carlson as first-rounders. Clearly, their rebuild started when drafted Ovie.
  • Pittsburgh is another outlier of sorts. Yes, they won a cup five years ago but this core also won one in 2009. So, any analysis I did on what it takes to win a cup, to get over the hump pivots around the ’09 Penguins. I would have thought that their rebuild starts with Sid, but clearly, they had bottomed out and drafted well before they got the lockout luck of picking first through a lottery. They drafted Fleury 1st overall in 2003, Malkin 2nd overall in 2004 and Crosby 1st overall in 2005. They added Letang in the 3rd Round in ’05 also. This was their cup-winning core.
As for the current contenders…
  • Colorado drafted Landeskog 2nd overall in 2011 and added MacKinnon first overall two years later and Rantanen 10th overall two years after that. This rebuild started with their captain Landeskog and we will see where it ends.
  • Carolina. This feels like Aho’s team. He was stolen in the 2nd round in their bottom out year when Hanifin was selected 5th overall in 2015. Let’s see where this goes.
  • Florida. Huberdeau was 3rd pick overall in 2011, Barkov was 2nd overall in 2013 and Eklbad was 1st overall in 2014. They bottomed out and started climbing back with the Huberdeau pick in 2011.
  • This is the sample size for this study. I am interested in seeing what we can learn from their paths to the Stanley Cup and how that might inform how we feel about our current voyage. To be completely transparent, I guess I wonder if patience is still the plan.
  • For comparative purposes, I have the Leafs rebuild starting in earnest when we drafted Marner 4th overall in 2015. I thought about Nylander or Rielly, but neither of those was the pick after a bottoming out. We could go with Matthews because he was the obvious rebuild kick-off, but we had a shot at McDavid the year we took Matthews, so it was just lottery luck that didn’t have us first overall that year.
ANALYSIS

The quick and obvious analysis is that if we are just looking at when the rebuild started and when a team won their first cup, how many years did it take?
  • The four Stanley Cup winners averaged 10.75 years. This average was lowered considerably by Pittsburgh winning it in 6 years. Tampa took 12, St. Louis 11 and Washington was 14.
  • As for the “contenders”, well Colorado and Florida are on year 11 and Carolina is on year 7.
The obvious conclusion is that it takes a long time to build a winner. The Leafs just passed their seventh year of this rebuild without a cup. A clock is ticking, but if we (or Carolina) had won it this year, it would have been one of the quickest ascents of the recent past.
Of course, “not winning the cup” is not a great measurement on its own. Lots of teams don’t win a cup. We want to know if we are heading in the right direction, and are making progress. Are we getting closer to the goal?

An obvious way to measure this is by measuring success. I didn’t even look at regular season metrics because I think we all know that regular-season success is not a predictor of playoff success. So, let’s look at playoff success – as measured by playoff games won and playoff series won.

Prior to winning their first cups, here is how these teams fared in the playoffs:
  • Tampa: 63 Playoff Games Won, 13 Playoff Series Won
  • St. Louis: 42 Games Won, 8 Series Won
  • Washington: 63 Games Won, 10 Series Won
  • Pittsburgh: 31 Games Won, 7 Series Won
They all won a lot of games and a lot of series. Indeed more than the “zero” series the Leafs have won so far. As for the “contenders”, up to this point and since their rebuilds started:

  • Colorado: 29 Playoff Games Won, 4 Series Won (including this year so far)
  • Carolina: 21 Playoff Games Won, 5 Series Won (including this year so far)
  • Florida: 12 Playoff Games Won, 1 Series Won (including this year so far)
What does this show us? These teams all won some playoff games and some series. The Leafs have 21 PO game wins and obviously zero series. However, the Leafs have only been at this for seven years and many of the teams above have been going at it longer (everyone except the Pittsburgh team that won in ’09 and the Hurricanes). So, how did these teams all do when it comes to playoff success in the first seven years of their rebuild?
  • Tampa: 25 Playoff Games Won, 5 Playoff Series Won, Missed the Playoffs 4 times
  • St. Louis: 10 Games Won, 1 Series Won, Missed the Playoffs 3 times
  • Washington: 17 Games Won, 1 Series Won, Missed the Playoffs 1 time
  • Pittsburgh: 31 Games Won, 7 Series Won, Missed the Playoffs 3 times (including LOCKOUT)
  • Colorado: 5 Playoff Games Won, 0 Series Won, Missed the Playoffs 5 times
  • Carolina: 21 Playoff Games Won, 5 Series Won, Missed the Playoffs 3 times
  • Florida: 5 Playoff Games Won, 0 Series Won, Missed the Playoffs 6 times
CONCLUSIONS

What did we learn from this? We see that most teams struggled mightily to achieve playoff success in the first seven years of a rebuild. Pittsburgh is the success outlier, but they did win a lottery to add Crosby to Malkin and Fleury. It’s interesting to see Colorado and Florida only won 5 playoff games and zero series each in their first seven years, while missing the playoffs 5 and 6 times respectively.

OK, so maybe our brand of suffering is not completely unique to the Leafs (55-year drought notwithstanding). This is what rebuilds look like, though all of the cup winners above had won at least one series in their first seven tries and that is what hurts. Having said this, only Tampa and Pittsburgh won more playoff games than the Leafs did in the first seven years after a rebuild and the Leafs are the only team to have never missed the playoffs in their window.

Where does this leave us? Maybe it makes a case for continued patience, but that is not the same as “standing Pat”. These teams all made moves, significant moves to support, augment and push their cores:
  • Tampa went through three coaches and two GMS before landing on Cooper and Brisebois (both unproven and no cups before TB). They also drafted well in later rounds and brought in McDonough to stabilize the D corps. They have mortgaged the future by adding vets for every playoff run.
  • St. Louis went through four coaches, and one GM change and made some big moves, including getting O’Rielly for their run. They also caught lighting in a bottle with Binnington on their run (they are an outlier)
  • Washington also had five coaches and two GMs but didn’t tinker as much with the core. They added vets and drafted some key pieces.
  • Pittsburgh. An outlier that won the Crosby lottery
The Leafs cannot be accused of standing Pat. They keep adding and tinkering. They changed coaches, and GMs replaced their starting goalie, signed a star centre and captain, traded for Muzzin, added Brodie, drafted and developed well (Sandin, Lijlegren, Engvall) and bought in vets around the edges (Foligno, Giordano, Blackwell).

What was the point of all of this? These are our last five cup winners and some current contenders. The winners show us it does take time and patience. The contenders appear to be telling us the same.

What else can we take from this?

If advocating for not being patient and blowing it up. Why?

If not blowing it up what tinkering can be done if we are learning from past champions?
 
This is a great write up, but it feels bias to start everyone elses rebuild back when they drafted their first highly picked player, but to have different methodology for choosing ours.

Also, I think you somewhat contradict yourself here:

OK, so maybe our brand of suffering is not completely unique to the Leafs (55-year drought notwithstanding). This is what rebuilds look like, though all of the cup winners above had won at least one series in their first seven tries
 
If you're going to start the clock for contenders like COL/TB/etc. with picks like Landeskog/Stamkos/etc. then you have to begin TOR's timeline at Rielly, which would be a decade.

Not to mention the Leafs have had more major asset management blunders than the other models over that timeline:

- Marleau's 3rd year cost 12th overall (Jarvis)
- Kadri trade botched (couple months of Barrie + 3rd liner)
- 1st + for a dozen games of an injured 33 year old Foligno
- Zero to show for the Kapanen trade (unfortunate cancer scenario)
- Marchment given away for free
- Verhaeghe given away for 1 year of Grabner in a tank season
- Trading down from Konecny pick to select Dermott
- Protecting Holl over McCann
- Hyman/JVR/Bozak/Gardiner/Komarov/Andersen/Barrie/etc. own rentals
- Absurd Zaitsev rush contract that cost Brown to dump
- Mrazek/Ritchie contracts will cost assets to dump

Some of these outcomes are the cost of being a contender (own rentals, TDL all-in moves), but it is a long laundry list of missed opportunity and wasted futures that will inevitably lead to a retool and longer process.
 
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This is a great write up, but it feels bias to start everyone elses rebuild back when they drafted their first highly picked player, but to have different methodology for choosing ours.

Also, I think you somewhat contradict yourself here:

OK, so maybe our brand of suffering is not completely unique to the Leafs (55-year drought notwithstanding). This is what rebuilds look like, though all of the cup winners above had won at least one series in their first seven tries
Thanks.

I am open to other ways to measure when each of these teams started their rebuilds. I tried not to be biased as I was not setting out to support or confirm a theory. I felt like St. Louis was the least clear, the others seemed to line up with what I think is the Leafs' rebuild chronology.

Yeah, that does read as a contradiction. Fair point. Maybe I should have said "even though we have been suffering for 55 years, we can really only hold this current rebuild accountable to itself and not the 48 years that preceded it."
 
If you're going to start the clock for contenders like COL/TB/etc. with picks like Landeskog/Stamkos/etc. then you have to begin TOR's timeline at Rielly, which would be a decade.

Not to mention the Leafs have had more major asset management blunders than the other models over that timeline:

- Marleau's 3rd year cost 12th overall (Jarvis)
- Kadri trade botched (couple months of Barrie + 3rd liner)
- 1st + for a dozen games of an injured 33 year old Foligno
- Zero to show for the Kapanen trade (unfortunate cancer scenario)
- Marchment given away for free
- Verhaeghe given away for 1 year of Grabner in a tank season
- Trading down from Konecny pick to select Dermott
- Protecting Holl over McCann
- Hyman/JVR/Bozak/Gardiner/Komarov/Andersen/Barrie/etc. own rentals
- Absurd Zaitsev rush contract that cost Brown to dump
- Mrazek/Ritchie contracts will cost assets to dump

Some of these outcomes are the cost of being a contender (own rentals, TDL all-in moves), but it is a long laundry list of missed opportunity and wasted futures that will inevitably lead to a retool and longer process.
I would break this feedback into two parts.

(1) When did the rebuild start?
(2) How are we doing?

For (1), can we really possibly consider this rebuild happening before Shanahan got here? He inherited a tea, that had Kessel, JVR, Bozak, Lupul, Phaneuf, Gardiner, Clarkson, Bernier and Reimer + they had traded two 1sts and a 2nd for Kessel. They were not in anyone's definition of a rebuild then. Shanny came in at the end of 2014, observed and assessed for a year and we didn't bottom out (were bad, but didn't bottom out) and drafted Nylander. He then stashed Nylander away, hired Lou, ran a fire sale and we bottomed out and drafted Marner the following year. IMO, this is why the rebuild starts with Mitch.

As for (2), I guess that's the question there. A few of those moves pre-dated the start of the rebuild (according to my start date), some of them were the previous GM and he is not here anymore, and some are on the current GM. If they don't win a cup then these will be mistakes, if they do win a cup then many of them will be viewed as "part of a process". Those other teams are not flawless either, Washington traded Forsberg for Erat, Tampa traded a bunch of high picks for Lindback, and I am sure St. Louis had some missteps too.

But this is a good conversation. If we can agree on when to start the metre we can start discussing how we are stacking up.
 
we should have never been buyers the first 2 seasons after drafting mathews we should have gained assets as we trimmed the fat away ie upcoming ufa's, own rentals ect

that along with the marleau signing and zatziev extention hindered us a lot more then people recognize, they blame the jt contract sure it was unnecessary but but the combination of marleau and zatziev making 10+ a season was worse considering who we had to sacrafice

the only 2 season i could justify us buying was t he last 2 as we were well positioned at the top the rest we should have just offloaded any ufas and packed those cudboards till they burst
 
Where does this leave us? Maybe it makes a case for continued patience, but that is not the same as “standing Pat”. These teams all made moves, significant moves to support, augment and push their cores:
  • Tampa went through three coaches and two GMS before landing on Cooper and Brisebois (both unproven and no cups before TB). They also drafted well in later rounds and brought in McDonough to stabilize the D corps. They have mortgaged the future by adding vets for every playoff run.
  • St. Louis went through four coaches, and one GM change and made some big moves, including getting O’Rielly for their run. They also caught lighting in a bottle with Binnington on their run (they are an outlier)
  • Washington also had five coaches and two GMs but didn’t tinker as much with the core. They added vets and drafted some key pieces.
  • Pittsburgh. An outlier that won the Crosby lottery
I highlighted this part because I believe it demonstrates one of the Leafs' largest failing - the inability to be successful drafting outside of high picks.
The part above hints at but doesn't quite directly identify a key component of these championship teams that the Maple Leafs have been lacking. Look at the players that each team drafted and developed outside of the lottery (or at least the top 10):

Tampa: Point, Kucherov. Killorn, Palat, etc. all outside of the 1st round.
St Louis: Binnington, Parayko, Edmundson outside of the 1st; Tarasenko and Schwartz in the teens. (Also Oshie late 1st).
Washington: Holtby, Orlov; Kuznetsov, Carlson late 1st. Wilson mid-1st.
Pittsburgh: Letang, Guentzel, Rust, Murray; Maatta late 1st. (Also Sheary but he was just getting started).

All of the winning teams had some high picks that were critical to their success and generally among their best players. But they had top 6 forwards, top 4 D, and starting goalies which they drafted and developed with selections outside of the top 10.

Who are the Leafs' comparable examples to these players? They have a few guys who might get there, but as of now there is basically nobody.

Right now this failure probably reflects more on the Hunter era since it's the draft picks from that regime who should be in prime time helping the Leafs compete right now. However, so far (emphasis on 'so far'), none of the Dubas' picks have had any significant impact. For many of those picks it's not fair to expect that yet, but some of them are at the point where it's reasonable to expect them to take a leap forward if they are going to be long-term contributors.

If analysis of the OP is correct that the Leafs should jump to serious contention over the next few years, then I believe we will need to see a few of the Leafs draft picks become key contributors. It won't be enough for Liljegren, Sandin, Robertson, Knies, etc. to be NHL'ers - at least 2 or 3 need to become top 6F / top 4D / starting goalie.

The above doesn't HAVE to happen - but it makes serious contention much more likely.
 
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The part above hints at but doesn't quite directly identify a key component of these championship teams that the Maple Leafs have been lacking. Look at the players that each team drafted and developed outside of the lottery (or at least the top 10):

Tampa: Point, Kucherov. Killorn, Palat, etc. all outside of the 1st round.
St Louis: Binnington, Parayko, Edmundson outside of the 1st; Tarasenko and Schwartz in the teens. (Also Oshie late 1st).
Washington: Holtby, Orlov; Kuznetsov, Carlson late 1st. Wilson mid-1st.
Pittsburgh: Letang, Guentzel, Rust, Murray; Maatta late 1st. (Also Sheary but he was just getting started).

All of the winning teams had some high picks that were critical to their success and generally among their best players. But they had top 6 forwards, top 4 D, and starting goalies which they drafted and developed with selections outside of the top 10.

Who are the Leafs' comparable examples to these players? They have a few guys who might get there, but as of now there is basically nobody.

Right now this failure probably reflects more on the Hunter era since it's the draft picks from that regime who should be in prime time helping the Leafs compete right now. However, so far (emphasis on 'so far'), none of the Dubas' picks have had any significant impact. For many of those picks it's not fair to expect that yet, but some of them are at the point where it's reasonable to expect them to take a leap forward if they are going to be long-term contributors.

If analysis of the OP is correct that the Leafs should jump to serious contention over the next few years, then I believe we will need to see a few of the Leafs draft picks become key contributors. It won't be enough for Liljegren, Sandin, Robertson, Knies, etc. to be NHL'ers - at least 2 or 3 need to become top 6F / top 4D / starting goalie.

The above doesn't HAVE to happen - but it makes serious contention much more likely.
I think that's a great point and the type of input I was hoping for. I wasn't trying to draw conclusions but rather wanted to level set and see what differences or further similarities we might find.

Needing to hit on non-lottery picks is a great point.

You mentioned a few that we need to find a few diamonds from. Which of the following can be impact players and soon enough to add to our core while they are in their primes?

Sandin
Liljegren
Engvall
Robertson
Knies
Niemala
Amirov
Woll

I guess we could throw the free wallets in there too, but that's only Mikheyev and he could be moving on.

There's enough of them on the list, but how many can realistically be too tier players?
 
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Might be grasping at straws at this point, but outside of Makar and Aho, our Matthews and Marner duo would still be younger than most star players powering these 2nd round teams. They're still younger than Point, Rantanen, Mackinnon, Barkov, Hubderdeau, McDavid, Draisaitl, Shesterkin, Ekblad, etc.
 
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Might be grasping at straws at this point, but outside of Makar and Aho, our Matthews and Marner duo would still be younger than most star players powering these 2nd round teams. They're still younger than Point, Rantanen, Mackinnon, Barkov, Hubderdeau, McDavid, Draisaitl, Shesterkin, Ekblad, etc.
If they missed the first three playoffs like most rebuilds do, or went in again out again over the Lou/dubas era but had still failed to win a round would everyone be as mad?
 
If they missed the first three playoffs like most rebuilds do, or went in again out again over the Lou/dubas era but had still failed to win a round would everyone be as mad?

At the time in 2016-17 I said we could either keep tanking, take the knee and scoop up another couple of extra core pieces or start winning right away. The former lets you add more quality to the system but latter means the quality and health of the organization is better than you thought.

So the Leafs kind of raced ahead in development, led everyone to believe they had sky high potential, which they still do, but fell behind vs expectations.
 
At the time in 2016-17 I said we could either keep tanking, take the knee and scoop up another couple of extra core pieces or start winning right away. The former lets you add more quality to the system but latter means the quality and health of the organization is better than you thought.

So the Leafs kind of raced ahead in development, led everyone to believe they had sky high potential, which they still do, but fell behind vs expectations.
Most of the growth came from the kids though, I would have never entertained the marleau deal myself so that definitely didn’t need to happen, and I could’ve done without the Plekanec or Boyle deals as well, but I’m not sure the cutting the legs off from under the team that was headed for a franchise point record by trading gardiner bozak & jvr made sense in the moment.
 
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I think that's a great point and the type of input I was hoping for. I wasn't trying to draw conclusions but rather wanted to level set and see what differences or further similarities we might find.

Needing to hit on non-lottery picks is a great point.

You mentioned a few that we need to find a few diamonds from. Which of the following can be impact players and soon enough to add to our core while they are in their primes?

Sandin
Liljegren
Engvall
Robertson
Knies
Niemala
Amirov
Woll

I guess we could throw the free wallets in there too, but that's only Mikheyev and he could be moving on.

There's enough of them on the list, but how many can realistically be too tier players?

From that list it's hard for me to guess at the guys who I haven't really seen play (Knies, Niemela, Amirov). I'll let people who have seen more of them chime in. Obviously a lot of people are very high on Knies right now, but a lot of people were very high on Robertson not long ago and that has cooled significantly.

Right now I feel like Liljegren and Sandin both have a chance to become top 4. I like Liljegren more because I think he's more well rounded and brings more of what the Leafs need, but I'm not sure if the Leafs see him as a part of the future. I would have played him over Holl more against the Lightning.

Engvall is a depth guy. Robertson doesn't impress me so far but it's too early to make a final declaration on him. Woll I have hopes for but the odds are against him. I think most fans don't think he will amount to anything,


EDIT: Most of the free wallets over the years have developed into depth guys when they work out. Which is still good, given the 'free' part! I think it's even harder to find an impact guy that way than with a draft pick.
 
If they missed the first three playoffs like most rebuilds do, or went in again out again over the Lou/dubas era but had still failed to win a round would everyone be as mad?
That's a great point. Who knows? Losing 7 straight series has really hurt, but the standard approach to a rebuild seems to be missing the playoffs two or three times and then struggling to find playoff success for a couple (a few) years.

Would only being knocked out three of four times in the first round feel differently for us?
 
If you're going to start the clock for contenders like COL/TB/etc. with picks like Landeskog/Stamkos/etc. then you have to begin TOR's timeline at Rielly, which would be a decade.

Not to mention the Leafs have had more major asset management blunders than the other models over that timeline:

- Marleau's 3rd year cost 12th overall (Jarvis)
- Kadri trade botched (couple months of Barrie + 3rd liner)
- 1st + for a dozen games of an injured 33 year old Foligno
- Zero to show for the Kapanen trade (unfortunate cancer scenario)
- Marchment given away for free
- Verhaeghe given away for 1 year of Grabner in a tank season
- Trading down from Konecny pick to select Dermott
- Protecting Holl over McCann
- Hyman/JVR/Bozak/Gardiner/Komarov/Andersen/Barrie/etc. own rentals
- Absurd Zaitsev rush contract that cost Brown to dump
- Mrazek/Ritchie contracts will cost assets to dump

Some of these outcomes are the cost of being a contender (own rentals, TDL all-in moves), but it is a long laundry list of missed opportunity and wasted futures that will inevitably lead to a retool and longer process.

The Seth Jarvis trade will come back to haunt us. He's 20 years old and already he's playing top line minutes in OT next to Aho. This will go down as the biggest knock on the current management group one day.

I think, above all the blunders we made, bringing in Tavares too early was the biggest. This set the salary expectations for the young guys, completely locked up any cap wiggle room, and quite frankly, he was the wrong player to target.

When we acquired JT, we thought our PP would be a big part of us dominating offensively. And yet, in the playoffs, our PP has sat around 12-14%. Complete non-factor.

My opinion is that we just straight up built the team incorrectly. It is supposed to overwhelm with it's skill, but we've bled all the depth away.
 
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The Leafs rebuild is coming along, although you definitely would have expected some more success by now.

But let's also keep in mind that things could be a lot worse. Teams like Buffalo and Arizona are perpetually rebuilding and there doesn't seem to be much glimmer of hope for any type of contention, any time soon.
 
Why are many assuming that the people who don't want to run it back want to blow it up/rebuild? Call me crazy for wanting the Leafs to make significant changes that make the team better suited for the playoffs while maintaining a top 10 regular season record.
 
What did we learn from this?
We paid too much for our core and spent too much on forwards.

I doubt any other team did that.

We also aren't really improving, just swapping deck chairs on the poorly constructed ship.

Getting Tavares was the mistake that accelerated the rebuild.

And Dubas should have known the players were not happy and wanted to take the team to the cleaners. You cant afford to overpay players in the cap era. You bridge players if they wont sign reasonable deals.

When we acquired JT, we thought our PP would be a big part of us dominating offensively. And yet, in the playoffs, our PP has sat around 12-14%. Complete non-factor.

Tampa really has an amazing power play. So much action. You can just feel the puck is going to go in.
 
If you're going to start the clock for contenders like COL/TB/etc. with picks like Landeskog/Stamkos/etc. then you have to begin TOR's timeline at Rielly, which would be a decade.

Not to mention the Leafs have had more major asset management blunders than the other models over that timeline:

- Marleau's 3rd year cost 12th overall (Jarvis)
- Kadri trade botched (couple months of Barrie + 3rd liner)
- 1st + for a dozen games of an injured 33 year old Foligno
- Zero to show for the Kapanen trade (unfortunate cancer scenario)
- Marchment given away for free
- Verhaeghe given away for 1 year of Grabner in a tank season
- Trading down from Konecny pick to select Dermott
- Protecting Holl over McCann
- Hyman/JVR/Bozak/Gardiner/Komarov/Andersen/Barrie/etc. own rentals
- Absurd Zaitsev rush contract that cost Brown to dump
- Mrazek/Ritchie contracts will cost assets to dump

Some of these outcomes are the cost of being a contender (own rentals, TDL all-in moves), but it is a long laundry list of missed opportunity and wasted futures that will inevitably lead to a retool and longer process.
You can't start Toronto's timeline from Rielly, because we really didn't rebuild that time. It was just one more failed year, that Burke benefit from. In hindsight you should start Blackhawks rebuild from drafting Keith, but basicly, it started years after and that organizational capital is always there, when you start rebuild. Change of vision and culture is more or less the start point. Early 2010s we tried to compete and the vision was to retool that bunch of mediocrity to cup winner with trade magic.

It nice to have hindsight on those moves, but you should always have some understanding over context and maybe look it from other franchises stand point also. You wont win every transaction, all top teams bleed assets. Slowly but steadily. It's name of the game at the moment with hard cap.

Marchment and Verhaeghe given free is nice statement of AHL players back then, that took years to develop after that. You can't keep two teams of worth of AHL players in the AHL. Marleau could have been kept, but that would have mean one lost season from this core, in hindsight easy to say that keep him for year since we lost anyway. You can pile that up with Kadri's trade and say that we shouldn't have signed Tavares, but in the end we'd lost Kadri now and don't have replacement here. That Kapanen take is terrible, it was good trade for us that ended up being real bummer, because of the cancer. Why is it there?

If I make one reasonable take now and here, because it's hindsight. I look up that list and say, we could have made slower build. Trade away those assets we had and don't push into playoffs. Don't sign Tavares at all. Would it have been better, might have been, but you never know. In reality we we're bubble team when we really tried and ended up being playoff team straight away. If you look other failed rebuilds it isn't that easy to become perennial playoff team with +100p seasons.

There is one big clear mistake, we didn't draft Aho instead of Dermott. I would have also changed Holl for McCann now and it can be argued if we could have made that decision even back then? But though Holl have progressed every year until now his development went backwards. That Holl-Muzzin could have been really good second pair like it was earlier.
 
The Seth Jarvis trade will come back to haunt us. He's 20 years old and already he's playing top line minutes in OT next to Aho. This will go down as the biggest knock on the current management group one day.

I think, above all the blunders we made, bringing in Tavares too early was the biggest. This set the salary expectations for the young guys, completely locked up any cap wiggle room, and quite frankly, he was the wrong player to target.

When we acquired JT, we thought our PP would be a big part of us dominating offensively. And yet, in the playoffs, our PP has sat around 12-14%. Complete non-factor.

My opinion is that we just straight up built the team incorrectly. It is supposed to overwhelm with it's skill, but we've bled all the depth away.
I don't think signing JT was a mistake, to this day it only looks bad in hindsight. Way more often than not you need 2 elite Cs to win the cup (among many other things) and at that time JT was the easiest pathway to having 2 elite Cs. I guess you could argue Dubas should have gotten creative and traded for someone like Ryan O'Reilly, but at that time their was an elite C available at the cost of no futures, only cap space.

The biggest mistake that sticks out to me is ironically Aho, who you brought up when mentioning the Marleau mistake. To me the 2016 and 2017 draft blunders were out of Shanny's hands as he let Lou do his thing who let Mark Hunter do his thing, which was draft a lot of busts.

But during the 2015 draft, the Leafs had not hired Lou yet, and Shanny basically divided up the interim GM role between Dubas and Hunter. He let Hunter run the draft and Dubas run everything else. It's pretty clear now and some were pretty adamant then that Dubas was a skilled drafter (maybe his only elite trait as an exec). At the very least he's a better drafter than Hunter.

Based on the skill that Dubas tends to lean towards, you could make the argument that Dubas would have selected Aho over Dermott. Aho's elite traits were pretty evident already heading into that draft. I was honestly surprised he wasn't taken in the 20s range of the 1st round. Imagine never needing to sign Tavares because you already have a homegrown drafted big 4 (2 of which are elite Cs) of Matthews/Aho/Marner/Nylander.
 
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I don't think signing JT was a mistake, to this day it only looks bad in hindsight. Way more often than not you need 2 elite Cs to win the cup (among many other things) and at that time JT was the easiest pathway to having 2 elite Cs. I guess you could argue Dubas should have gotten creative and traded for someone like Ryan O'Reilly, but at that time their was an elite C available at the cost of no futures, only cap space.

The biggest mistake that sticks out to me is ironically Aho, who you brought up when mentioning the Marleau mistake. To me the 2016 and 2017 draft blunders were out of Shanny's hands as he let Lou do his thing who let Mark Hunter do his thing, which was draft a lot of busts.

But during the 2015 draft, the Leafs had not hired Lou yet, and Shanny basically divided up the interim GM role between Dubas and Hunter. He let Hunter run the draft and Dubas run everything else. It's pretty clear now and some were pretty adamant then that Dubas was a skilled drafter (maybe his only elite trait as an exec). At the very least he's a better drafter than Hunter.

Based on the skill that Dubas tends to lean towards, you could make the argument that Dubas would have selected Aho over Dermott. Aho's elite traits were pretty evident already heading into that draft. I was honestly surprised he wasn't taken in at least the 20s range of the 1st round. Imagine never needing to sign Tavares because you already have a homegrown drafted big 4 (2 of which are elite Cs) of Matthews/Aho/Marner/Nylander.

The JT signing is a mistake because half our cap was allocated to 4 players, all forwards. Everyone knew this was not going to work, and it hasn't. Yes, can say COVI messed things up, but it messed Tampa up too.

One thing which really separates us from Tampa and Colorado is that neither of them have a really inefficient contract on their rosters. We have Tavares, Muzzin and Mrazek. The lost cap dollars on those inefficient deals add up to players like Paul, Hagel, Palat, etc.

Tampa had one in Johnson but the league bailed them out.
 
The JT signing is a mistake because half our cap was allocated to 4 players, all forwards. Everyone knew this was not going to work, and it hasn't. Yes, can say COVI messed things up, but it messed Tampa up too.

One thing which really separates us from Tampa and Colorado is that neither of them have a really inefficient contract on their rosters. We have Tavares, Muzzin and Mrazek. The lost cap dollars on those inefficient deals add up to players like Paul, Hagel, Palat, etc.

Tampa had one in Johnson but the league bailed them out.
Dubas' blind loyalty to Marner and Nylander doesn't change the fact that true contenders way more often than not need 2 elite centres to win the cup among other things. But among all the pieces a contender needs elite centres are one of the hardest pieces to acquire, and JT was available at the cost of trading no futures.

When the signing first happened I didn't see it as a big 4 type situation. I saw it as the Leafs now have Matthews and JT down the middle long term. Dubas made it into a big 4 situation with his blind loyalty to Marner and Nylander, and disgusting overpayment to Marner specifically.
 
And why is Chicago and Los Angeles not mentioned at all? Chicago starting out with Toews, Kane, Keith and many other young players plus several star veterans is only the closest to the situation here. Maybe Chicago is ignored so you could label Pittsburgh as an outlier. Like many unscientific treatments that take on the air of impartial science, it feels like the conclusions preceded the words.

Literally NONE of the last 10 Cup winners lost more than 2 consecutive 1st round playoff series before going deep into the playoffs. St. Louis is the closest the Leafs' consecutive failures with some close playoff misses in place of 1st round losses but also St. Louis wasn't privileged with any individual forward of the abilities of Marner, Matthews and Nylander until Tarasanko emerged.

The fact remains that this serial failure to win a single 1st round series in 6 consecutive seasons is an unprecedented event. No franchise has done this and emerged later as championship caliber. To say there could be a first, okay I'll accept that. But let's not pretend that this isn't a trend. And for the most part trends predict future events.
 
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And why is Chicago and Los Angeles not mentioned at all? Chicago starting out with Toews, Kane, Keith and many other young players plus several star veterans is only the closest to the situation here. Maybe Chicago is ignored so you could label Pittsburgh as an outlier. Like many unscientific treatments that take on the air of impartial science, it feels like the conclusions preceded the words.
I did run it back to Chicago in my original analysis, but at some point, the game and league changes enough that comparisons are no longer as relevant. We were just entering the cap era, and it was low too. Chicago won in '09 for the first time, two years after drafting Kane (after drafting Toews the year before). Using the logic in this thread, wouldn't the rebuild actually have started (poorly) in '04 with Cam Barker 3rd overall and Jack Skille 7th overall in '05? This team had missed the playoffs for 9 out of 10 years (winning one PO game the year they did make it) before going to the Conference Final with Kane and Toews on board joining Keith and Seabrook.

It just seemed too much of a different era and dynamic to try to call it an apple to compare to our apple.

As I said, I am open to differing opinions on this, but 5 years seemed like a reasonable amount of time to go back. With the Penguins being champs 5 and 6 years ago but this core also having won previously it did allow me to go back a bit on that one.
 

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