Exploring Maple Leafs 'What Ifs' with 6 key decisions from the Brendan Shanahan era

Its over.

The Brendan Shanahan era is done, Mitch Marner is all but gone and big changes seem imminent in Toronto.

The Maple Leafs, or at least this version of them, have failed.

Did it have to be this way? Thats the big question these days.

To hear some tell it, yes, this was the inevitable outcome all along because playing in a big market like Toronto is just too much to ask from the toughest athletes in the world .

Others would tell you that the Shanaplan was doomed from the very start because it was built around the wrong core.

And some would just shake their heads and mutter something about being cursed.

Advertisement Then theres the side that says no, it didnt have to be this way that there were multiple branching paths along the road that made a different destination possible.

Thats the premise of todays piece, as we look at a half-dozen key checkpoints in recent Maple Leafs history, and wonder what would have happened if a different decision had been made.

Our starting point here is 2018 or so.

The Leafs have already drafted Auston Matthews, Mitch Marner and William Nylander.

Theyve made a surprise playoff run in their first year together , then nearly knocked off the established Bruins in year two.

Shanahan has a plan, and its working.

While theres a long way to go, the future is as bright as its ever been.

And then ...

well, we know what comes next.

But what if? We wont go too deep down the alternate history hole on any of these if youre looking for fan fiction that ends with the Leafs winning all the Cups, youll have to write it yourself but each is worth exploring.

And at the end, Ill even let you tell me the right answer.

What if: Theyd stuck with Lamoriello? This feels like an interesting place to start, because while it comes first in our chronology, it almost feels like a forgotten moment in the Leafs evolution, or at least one you dont hear about as often as some of the others well get to.

But at the time, it felt like a monumental shift.

The Leafs had hired Lou Lamoriello as GM in 2015, a truly shocking moment that broke the bizarro-meter .

Lamoriello had been with the Devils since 1987, and had recently been shuffled upstairs at the age of 72, where we all assumed hed spend his remaining NHL years.

Instead, Shanahan swooped in and hired his old boss, giving the rebuilding Leafs some instant credibility, not to mention a mentor for Kyle Dubas and Mark Hunter.

Advertisement But by 2018, it was clear a decision had to be made.

Lamoriello had done a reasonably good job in Toronto, making some solid moves while working toward Shanahans goal of changing the culture.

But other teams were starting to circle around Dubas and Hunter, and Shanahan had to make a choice on who would lead the team into the future.

He chose Dubas.

At the time, it was widely viewed as a hard decision, but the right one .

What if the Leafs had stuck with the known quantity, trusting the veteran Lamoriello to keep the plan on track, even if it meant losing Dubas? Lamoriello ended up joining the Islanders, where his track record was decidedly mixed.

He took over a team everyone assumed would be awful and guided them to back-to-back conference finals appearances.

He also got too bogged down in his old-school ways, handing out big contracts to role players and leaving the cupboard largely bare.

Its hard to say whether the Leafs would have been better if Shanahan had kept his old pal in charge.

Certainly, the Dubas era had its own share of hits and misses, moves that will be litigated for years to come in Toronto.

At the very least, Lamoriello wasnt exactly known for his patient approach, and its hard to imagine him sticking with underperforming coaches and players during what became the Leafs run-it-back era.

Would they have won anything? Maybe not, but they wouldnt have seemed satisfied with that outcome.

What if: Theyd passed on Tavares? This feels like the big one, right? Back in the summer of 2018, Leafs fans were thrilled to land Tavares , arguably the biggest UFA prize of the last decade.

Two years after being spurned by Steven Stamkos, here was a genuine superstar who was choosing to come home and embrace the pressure of chasing a Stanley Cup in Toronto.

He could be a difference-maker on the ice and a role model for the teams younger players off of it.

Even a cynic (raises hand) had to love the whole childhood dream schtick .

And, we were told, he even left money on the table to do it.

Advertisement But ...

did he? How much? While Tavares reportedly had bigger offers elsewhere, he didnt exactly give the Leafs a steep hometown discount, signing for an $11 million cap hit that made him the leagues second-highest-paid player, trailing only Connor McDavid.

At the time, the mostly positive response assumed that the message from the Tavares signing to fans was This young team is ready to go out and win it all.

And maybe it was.

But in hindsight, there was a secondary message to those young Leafs that the new captain would be leading: Torontos great, but make sure you still get that paycheck.

Hometown discounts are for chumps.

OK, thats probably harsh.

But with Matthews and Marner both needing extensions over the next year, it suddenly became difficult for the Leafs to play the everyone is taking less to win card.

And if they even tried, the players sure didnt buy it .

On the ice, Tavares was very good, with gusts up to great.

He basically spent seven years threading a frustrating needle not quite dominant enough to justify his massive cap hit, but nowhere near bad enough that you could call him a bust.

He was a good player who was overpaid.

And that ended up becoming the Maple Leafs way.

What if theyd passed on Tavares, letting him go to Dallas or San Jose or wherever else while focusing that $11 million on building a supporting roster for the young core? Maybe even a defenseman or two? Maybe it would have worked out.

Or maybe Matthews never becomes an MVP and Marner never becomes a 100-point threat if they dont have an established star forward to learn from.

Of course, were missing one piece of that core here, so lets try another contract-related what if.

What if: Theyd let Nylander sit the season? In the aftermath of the Tavares signing, Dubas uttered his infamous We can and we will vow about keeping his Core Four together.

The first test came a few months later, with Nylander needing a new deal.

With negotiations dragging through the summer and into camp and then into the season, it began to look like it was possible that Nylander could become the rare young player to sit out an entire season for lack of a contract .

Advertisement Those concerns vanished on December 1, as a deal came together with minutes to spare before a CBA-imposed deadline.

Nylander signed for six years at an AAV of just under $7 million less than Leon Draisaitl had just gotten, but more than David Pastrnak.

At the time, it felt high, but reasonable.

In hindsight, it was largely a bargain.

But what if the Leafs had held firm, sacrificing Nylanders season to send a message to their young players that the monster second contracts werent on the table? Its possible that this could have lightened the load on the eventual Matthews and (especially) Marner extensions, two deals that crowded the cap and made the players lightning rods for criticism.

This was the Leafs first and really only chance to make it clear that holding the line on cap hits was a priority.

Instead, they opened the floodgates.

Of course, Nylander eventually lived up to his deal, which led to another far larger one .

While Nylander didnt play well in that 2018-19 season, its possible he never develops into the player he is today if he loses that entire year.

And maybe the Leafs taking the hard line even fractures the relationship, or divides the dressing room.

Im guessing most fans would point to Marner or maybe Matthews second contracts as the ones where the Leafs should have held the line.

Im just not sure thats realistic after the deals they gave Tavares and Nylander were already in place.

But since were focused on the cap right now, lets do one more in the same area ...

What if: The cap hadnt gone flat? Heres my least-sexy Maple Leafs take: The Shanaplan would have worked if they hadnt been messed up by the flat cap.

Thats an unsatisfying opinion because it doesnt assign any blame for the cap problems that became a long-running storyline.

It wasnt greedy players or a spineless GM or manipulative agents.

It was just an unprecedented worldwide pandemic, one that led to the cap going unexpectedly flat for years to come.

And sure, that flat cap hurt every team.

But it hurt the Leafs the most, because of the timing they were the team that had just locked up its entire core on contracts that were supposed to reset the market.

Maybe they would have, until COVID came along and reset it right back.

Advertisement Keep all those pre-2020 contracts in place, and just have the cap keep creeping up the same way it always had.

Now the Leafs have plenty of room for everyone.

They can re-sign Zach Hyman, rather than letting him walk right before he becomes a 50-goal scorer.

They can even add a few reinforcements along the way.

And they do it all while other stars around the league are signing deals that make Matthews and Tavares and Marners look reasonable, which takes some of the pressure off in a market stuffed with it.

Instead, they were mired in cap hell not because they messed up, but because the rules changed midway through the game.

Nobodys fault, just bad luck.

Like I said, not very satisfying.

So lets take this back to the areas the team could control.

What if: Theyd fired Sheldon Keefe in 2021? The 2021 playoffs were the first time that it felt like something about this team was broken.

Back-to-back losses to a good Bruins team had been disappointing, but they were close.

Losing to the Blue Jackets in 2020 was a step back, but it was the bubble and maybe you just couldnt draw any conclusions.

But losing to the Habs, while blowing a 3-1 series lead , in a year where their path through the playoffs would never be easier? Inexcusable.

Or at least, it should have been.

At the time, it felt like big changes were obviously needed .

Of course, they didnt happen, because they never happen in Toronto.

But even if we assume that the Leafs werent going to trade Marner for Jack Eichel or fire the whole front office, what about a coaching change? Surely that would be the bare minimum, given Keefe had just been outcoached by Dominique Ducharme.

Instead, Keefe lasted three more seasons, all of which ended with further playoff disappointment.

He left as the Leafs most successful coach of all time, in terms of regular-season points percentage, while only winning a single round in five tries.

Could the Leafs have found somebody better? Maybe other coaches hired in the aftermath of that season included Gerard Gallant and Bruce Boudreau, and names like Rick Tocchet and John Tortorella were also available.

Maybe the Leafs would have even hired Spencer Carbery out of the AHL as head coach instead of an assistant.

Then again, maybe theyd have gone with Brad Larsen or Dave Hakstol or Ralph Krueger.

We cant say how that would have turned out.

But we can say this: Making a big change after the disaster of 2021 would have sent a clear message to the roster that losing like that was unacceptable, and that failure had consequences.

Advertisement That was a message the team never seemed all that comfortable sending.

The teams unofficial motto, dating back to the Conn Smythe days, has been Defeat does not rest lightly on their shoulders, except that for the last few years, it kind of has.

Maybe holding Keefe accountable would have changed that.

Or maybe it would have just been a largely symbolic gesture that would have made the team worse.

OK, one more ...

What if: Theyd traded Marner when they could? This one could cover almost all of Marners career, but Im specifically referring to the 2023 offseason.

That was the one that saw Shanahan make the controversial and confusing decision to move on from Dubas , not simply due to a lack of results but because of a disconnect between the two over ...

something.

We could certainly include that decision as another what if moment, although Dubas hasnt exactly made the Leafs look bad in his two years in Pittsburgh since.

Instead, lets focus on the timing.

When Dubas was shown the door, we were almost six weeks away from July 1.

When Brad Treliving officially arrived as the replacement , it was May 31.

And the immediate question was clear: Would he make any big moves? That July 1 date mattered, because it was when both Marner and Matthews would have full no-move clauses kick in.

Treliving could have moved either, or both at least in theory.

Whether he ever seriously considered it is another question.

Whether Shanahan would have allowed it is yet another.

One thing we do know for sure: There was time to get it done.

Not a ton, obviously, and certainly not as much time as NHL GMs typically tell us is required for major trades.

But nobody really buys that, and rightly so.

Treliving himself was less than a year removed from pulling off a blockbuster in Calgary, one that had come after Matthew Tkachuk indicated he wouldnt sign an extension with the Flames.

Total time elapsed between Tkachuk making that decision and Treliving finalizing the biggest trade the NHL had seen in years, one which included an unprecedented sign-and-trade: one whole week .

So yes, one month was more than enough time to move Marner before his trade protection kicked in.

But the team never really seemed to consider it, and in fact reports suggested that Shanahan had already assured the core they werent going anywhere.

It didnt have to be that way, and this isnt just hindsight talking at the time, the Leafs refusal to even consider big changes was seen as unusual .

But Treliving stayed the course.

Advertisement We know how that worked out.

Marner put together a strong season, followed by a disappointing playoff, then went into the final year of his deal with little indication that an extension would happen.

He had yet another strong season followed by yet another disappointing playoff, refusing a potential trade to Carolina in between.

And how hes almost certain to walk, with the Leafs getting nothing in return beyond cap space for a 100-point player in his prime.

That doesnt feel like the sort of asset management that helps build a championship roster, but its the path the Leafs chose.

And despite some attempts to retcon the timing, it was a choice.

That was sad.

And I dont really have a witty ending here, in part because were still waiting to see the extent of what other changes will come.

So as we wait, all of us poking at the Maple Leafs carcass with a stick and begging it to do something, Ill turn it over to you.

If you could go back and change the result of one of the decisions above, which one would it be? Loading...

(Top photo of John Tavares and William Nylander: Sam Navarro / Imagn Images).

This article has been shared from the original article on theathleticuk, here is the link to the original article.