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Losing Masai Ujiri would be a painful blow, but he’s set the Raptors up to survive it

Masai Ujiri is one of the best executives in the NBA. Could the Raptors continue their run of success without him?

NBA: NBA Draft Lottery Brad Penner-USA TODAY Sports

Stability has ruled the Raptors under the measured leadership of Masai Ujiri. The Raptors are a collaborative entity, each level of the chain of command providing support for the one above it. Four years ago the Toronto was a laughing stock. Today, it is one of the league’s model franchises, at least as far as continuity is concerned.

A favourable light shines upon all successful organizations. Under that spotlight, it becomes nearly impossible to hoard smart people in secrecy. The have-nots are inevitably going to want to replicate the haves; the more enviable a team’s position, the more prone it is to having its talent poached.

It shouldn’t have surprised anyone to learn, then, that the Knicks — a dumpster fire without the luxury of burning in a hidden back alley — are interested in nabbing Ujiri from the Raptors, as Adrian Wojnarowski reported Wednesday morning. New York had been rumoured interested in Toronto’s boss last summer as well. With the Phil Jackson clown show coming to an end this week, the rumour’s re-ignition was to be expected. Despite the team’s desecration under Dolan, the Knicks have enough caché to perpetually be in the hunt for top front office candidates. We’ve seen a similar effect with the Raptors’ very own roommates. Even with a decade-plus of stench on the Maple Leafs’ name, the allure the Leafs (along with a record amount of money) was enough to convince Mike Babcock to leave a comfy situation in Detroit to take on the most impossible challenge in hockey: fixing the league’s unfixable marquee franchise. No one at the top of their field has a suppressed enough ego to think “I can’t do that job.” None of this is to say Ujiri will definitely follow a similar path to Babcock and bolt for the Knicks, but the the rationale for why he might be drawn to the floundering Knicks is enough to have people on edge.

Raptors fans have never been here before. Usually when the end of an executive's time with the team appears nigh, fans are already in the process of shooing him away. No one wept when Bryan Colangelo's run of half measures and desperate win-now ploys came to an end. Same goes for Rob Babcock, and Glen Grunwald, and Isiah Thomas before them all.

Ujiri is different. While he didn't put the Raptors core in place, he has been the catalyst behind the most drastic organizational overhaul we’ve seen in the last 23 years. Toronto is no longer a jokey outpost. When Ujiri came to town, they were trying to shoehorn Rudy into an offense with pre-ascension DeMar DeRozan and Kyle Lowry. Now, the Raptors are among the most stable and profitable entities in the NBA.

Just as, if not more endearing than his savvy deal for Norman Powell or bolstering of the franchise's image, is Ujiri's work outside of Raptors duties. Ujiri spends his summers — and winters — pouring his life into Basketball Without Borders and Giants of Africa, programs making a tangible difference for people abroad. Even if he were to achieve the impossible and bring a title back to Madison Square Garden, Ujiri's lasting legacy as an executive will likely be dictated by the good he has done for his homeland, not the number of rings on his fingers. Losing a figurehead with such gravitas and worldly importance would be a painful blow for the Raptors to absorb. Ujiri is charismatic, with a knack for well-timed profanity. He's an example and source of hope for immigrants and people of colour hoping to break into the most white-dominated sphere of pro sports. Nitpick with the Bruno Caboclo pick or DeMarre Carroll contract all you want, but Ujiri is damn near unimpeachable in Toronto, for far grander reasons than four-straight playoff appearances.

Losing him, to James Dolan and the Knicks of all people and teams, would be a fucking gut punch. There's a chance that punch could knock the wind clean out of the organization. Apart from a few fleeting moments under Grunwald and Colangelo, the Raptors have never known normal. Without Ujiri's leadership, it's entirely possible the team could revert back to its directionless 2012 form. Ujiri may be so singularly brilliant that a departure could resemble a supervolcano wiping out a society, erasing all of its knowledge in the process. Fans of this franchise have only seen sustainability under Ujiri. It’s human nature for people to be fearful of what life might be like without him guiding everything the Raptors do.

To assume the Raptors immediate disintegration in the event Masai leaves, however, is to take a bit of a shot at the body of work he has put in.

These aren't the franchise's dark ages anymore. Four years of winning, playoff series wins, the evolution of the team's star players and coaches — all of these things can be sustained and built upon without Ujiri in the fold. The front office trio of Bobby Webster, Dan Tolzman and Keith Boyarsky aren't the proven entity Ujiri is, nor are they as magnanimous beyond the walls of the Air Canada Centre. But they are products of Toronto's new, Ujiri-crafted culture; home grown talents, groomed by their boss as part of his always-pumping pipeline of organizational talent. Barring an unlikely house cleaning upon Ujiri’s hypothetical move, his apprentices will at the very least have Ujiri’s blueprint in hand. Whether or not they’re capable of executing his vision would be learned in the coming years. It is by no means a sure bet that they’d be up to the task. Ujiri clearly believes in them enough to have them in the positions they hold today, though. If Masai is the visionary most people view him to be, his seal of approval has to count for something.

Moving down the Raptors’ ranks are more known commodities. Dwane Casey could have been let go during Ujiri's first summer in office and no one would have caused a fuss. Instead, he's used the last four years to evolve and improve. He has his foibles, and definitely his detractors, but he and the promising young staff behind him are every bit the support beam that Ujiri is, albeit perhaps less of a weight-bearing one.

From top to bottom, the organization is in a demonstrably better place today than it was when Ujiri took office. Ujiri’s genius is the primary reason for that growth, of course. But even if he were to leave, taking a healthy chunk of the Raptors’ organizational equity with him, Toronto would still be left in a better-than-average position to regroup and move forward from.

There is a very real chance this speculation and fear results in nothing more than a bunch of wasted breath and ink. While things in the NBA can change in an instant, some roadblocks stand in the way of Ujiri taking over Jackson’s vacated seat.

Most notably, is the compensation the Knicks would have to send Toronto’s way. If Jeff Weltman is worth a second rounder likely to land in the mid-30s, Ujiri’s base value should be at least one first round pick, if not more. The Knicks, with their talent-bereft roster, are in more dire need of draft picks than almost any other team in the league. A move to the Knicks by Ujiri would almost mirror a situation he once engineered with Carmelo Anthony — he’d be headed to his desired location, but gutting the team’s asset stores in the process.

ESPN’s Ramona Shelburne had this to say yesterday about the Knicks’ interest in surrendering picks to land Ujiri in her piece on Jackson’s ouster.

As for reports that the Knicks were interested in Toronto Raptors president Masai Ujiri, sources told ESPN that the Knicks have a deep respect for him, but he's under contract and thus would require permission to speak to and compensation -- likely draft picks -- which the Knicks would be very reluctant to consider.

The Raptors also received a second round pick when Jeff Weltman was hired by the Orlando Magic, so the price to get Masai would be very high. -

In the event the Knicks do pay the price to land Dolan’s prized target, that would leave Webster and company more resources to help make life after Ujiri more livable. The Knicks aren’t a piece or two away from contention; a first-round pick for Ujiri would carry some serious value.

Of course a draft pick would only be a small consolation for those who view Ujiri almost like a family member — which is probably a large subset of the fan base. There is no denying that the Raptors would be hurt if he were to take up residence in MSG. Factoring all of Ujiri’s virtues, there might not be a more irreplaceable executive in the league.

It’s because of the abilities that make him so attractive to New York, though, that the Raptors are set up to maintain some semblance of the identity Ujiri fostered should he leave.