TORONTO, ON - JULY 20 - Kawhi Leonard basketball jerseys and John Tavares hockey sweaters are modeled at the entrance to Real Sports Apparel inside Scotiabank Arena, Toronto. Earlier, Toronto Raptors President Masai Ujiri talked to the media during a press conference about the DeMar DeRozan-Kawhi Leonard trade. July 20, 2018. Bernard Weil/Toronto Star (Bernard Weil/Toronto Star via Getty Images)

Toronto Maple Leafs Will Not Win the Stanley Cup by Hunter Eitel

While assembling the recruitment plan to unite John Tavares and the Toronto Maple Leafs, Kyle Dubas sought advice from fellow MLSE executives.

Reportedly, that group included none other than Toronto Raptors President, Masai Ujiri. For good reason, too. To prepare for the unprecedented, seeking guidance from a world that views these exact moves as routinely mundane is a good place to start.

It worked.

Glowing in the aftermath of his plan’s fruition, Dubas sat alongside Tavares and gave a fleeting glimpse into how he brought his prized asset home.

“Bobby and Masai and Teresa with the Raptors were a great resource for us,” Dubas explained.

“We’d be foolish not to. They’ve been through this a lot more than us.”

Going off what transpired this past week, it appears they may be of more help than previously thought. There’s much for Masai to impart upon his bespectacled colleague. Lessons that, while painful in execution, are crucial in paving the path to success.

They aren’t easy. Then again, winning never is.

Setting the Scene

Amidst what many proclaim to be the “slowest week in sports”, the Raptors took great lengths in making it anything but.

Following months of trade rumours and organizational tension, the San Antonio Spurs mercifully relented, dealing their (when healthy) perennial MVP candidate, Kawhi Leonard, to Toronto. Going the other way was a Raptors package consisting of Jakob Poeltl and a top-20 protected 1st round pick.

Oh, and DeMar DeRozan. Can’t forget him.

Spurs have agree to trade Kawhi Leonard and Danny Green to Toronto for DeMar DeRozan, Jakob Poeltl and a protected 2019 first-round pick, league sources tell ESPN. Trade call with league office is starting shortly. — Adrian Wojnarowski (@wojespn) July 18, 2018

It’s safe to label the optics of this trade as controversial. Albeit, not for who the Raptors got.

Leonard is a bonafide superstar, a franchise-altering talent whose resume glistens with accolades including two Defensive Player of the Year Awards, multiple top-5 finishes in MVP voting and a Finals MVP. Largely regarded as the lone player capable of neutralizing LeBron James, Leonard joins the very organization James has pillaged for the past three years. How could this be anything but a win?

Well, it took DeMar to get him. And fans aren’t happy.

DeRozan is far from a typical franchise face. His unwavering loyalty to Toronto was not only endearing, it came at a time when the market’s allure was toxic. The Raptors were, until recently, perceived as radioactive. Deemed the NBA’s red-headed Canadian stepchild, networks south of the border paid them little attention, many going so far as to ignore them altogether.

DeRozan changed that.

In nine years with the team, he established franchise bests in nearly every meaningful statistical category, becoming the only Raptor to sign three consecutive contracts with the team in the process.

And just like that, he’s gone. With no chance to say goodbye.

No Pain No Gain

Running a professional sports team is not an easy job. At some point, GM’s find themselves stuck at a crossroads, staring down two distinct paths forcing them to make a choice. The first path leads to success, the other to comfortable mediocrity.

I’ll let you guess which one is more painful.

Is this GM willing to make a tough, at times heartwrenching decision for the betterment and sustained success of his team? Or, is coasting into the either of meaninglessness and inevitable unemployment more his speed?

It’s this choice that defines legacies, births dynasties and reveals true character. On Wednesday, Masai stood at that exact crossroad. One day, Dubas will too.

In dealing his team’s beating heart, Masai clearly chose the former. The decision to jettison DeRozan is exactly that, heartwrenching, but one of undoubted necessity. Across DeRozan’s near-decade at the helm, the Raptors had yet to win. Their future looked primed for even less.

Propping their contention window open had only one outcome. DeRozan had to go.

The Leafs

For the Leafs, 2018-19 nudges their core past their window’s beginning and into their prime. It’s a window that, if managed correctly, should stay open for years to come.

To ensure this, grating decisions will inevitably arise, with Dubas being the one to make them.

Such difficulty is even more prevalent in the NHL, whose hard cap lacks the flexibility of the NBA’s luxury tax structure. Hockey leaves no room to wiggle with, no outright benefits for the rich. You’re either over the cap or under it. There is no in-between.

It’s this rigidity that curses teams with personnel decisions of extreme complexity. Whereas the NBA offers stretch provisions to clear cap space for budding contenders, the NHL’s best offer is LTIR.

Now, with the significant raises of Auston Matthews, William Nylander and Mitch Marner adding to Tavares’ figure of $11 million in the next 12 months, how Dubas manages their surroundings will be of extreme importance. The locker room dynamic must adapt on the fly.

Loyalty, regardless of the player in question, only takes you so far. A hard capped league leaves no room for it. Time and time again, it’s a pitfall crippling all who ignore it.

The evidence is ever present.

Detroit and Vancouver willfully shower depth players with salary and term, effectively stunting any hope of future success. Loyalty motivates The Kings’ refusal to part ways with their previously effective contributors, like Dustin Brown, whose age and albatross cap hit shackle them to mediocrity.

These are teams who, when barreling towards their crossroad, chose the path of least pain. They chose to eschew difficulty for comfortability. Look where it’s left them.

It won’t be long before Dubas reaches the same crossroad. Not today, not tomorrow, but that day will come. And when it does, guidance for handling will sit just down the 40 Bay Street halls.

Dubas leaned on Masai once, successfully. It’s only a matter of time before he should do it again.

Thanks for reading!