The Raptors knew they were taking a big risk when they pulled the trigger on the trade for Kawhi Leonard a week short of a year ago. For one thing, he was set to become a one-season rental; free agency in 2019 beckoned, and his camp made no secret of his preference to play in native California. For another, they needed to give up their identity in the process; the Spurs wanted another superstar, and specifically DeMar DeRozan, who, as their ninth overall pick in the 2009 draft, relished being the face of a franchise otherwise lacking in pull. Giving him up meant redefining the unique culture they had built and fortified; yes, they ran their affairs professionally, but they were a family first and foremost, and they took care of their own.

For the Raptors, DeRozan’s utter absence of wanderlust was especially critical as they made a name for themselves in the National Basketball Association. No big name hitherto seemed to view Toronto as a worthy destination, with cross-border concerns — among them distance from loved ones, prohibitive income taxes, and temperate weather — hanging like an albatross around its neck. Meanwhile, draftees who became bona fide headliners appeared to want to move elsewhere as soon as possible. Yet, there he was proudly trumpeting his love of city and colors. In hockey nation, he held his head high for red-and-black hoops, and how.

In dealing for Leonard, the Raptors effectively sent the message that winning trumps everything — even relationships built over time, effort, and no small measure of affection. It’s why DeRozan was heartbroken and bitter when he learned of the news; likewise, it didn’t help that front-office head Masai Ujiri just gave him assurances that he would continue to be part of their future. Still, on the basis of improving the principal product on the court, they were right to go for the swap. The roster, while boasting of continuity, had reached its ceiling and needed a makeover. And what better way to reboot than truly compete for the title?

Well, the Raptors didn’t just go on to contend. They went all the way. And if only because the Larry O’Brien Trophy sits on their mantel, their bid for Leonard cannot but be deemed an unqualified success. If nothing else, it highlighted how well they went about their business; they had the vision to guide them, the strategy to see their objectives through, the gumption to gamble, the foresight to stick to their guns, and the competence to make sure all fell into place. As much as they wanted to win, they exercised extreme caution with their new star; through the regular season, they put in place a load management program that followed the league’s Player Resting Policy and ensured he would be fresh for what they figured to be a deep playoff run. And, ultimately, they were rewarded with the hardware.

To be sure, the Raptors benefited from sheer good fortune countless times during their journey to the top. They were close to being eliminated by the Sixers in the second round, for instance, with four bounces on the very last shot of the series literally deciding their fate. They ran against the decimated Warriors in the Finals. Then again, there can be no discounting the fact that they placed themselves in the best position to benefit from twists of fate. They went all in last season, and it paid off handsomely. They managed to render irrelevant their past as whipping boys of LeBron James by establishing their present as dynasty killers.

There was still the future to secure, though, so the Raptors buckled down to work pronto. The short turnaround time from celebration to free agency afforded them no rest. And, for all the strides they made with Leonard, they knew they were going to negotiate from a position of weakness. All the signs were there from the outset, and even while they were in the midst of meeting their date with destiny. He aimed to go home, and only an outstanding presentation could sway him into changing his mind. And in prepping for their pitch, they asked him for only one thing: that they be the last to lay their arguments.

In retrospect, there was nothing the Raptors could have done differently. It didn’t matter that they cultivated their relationship with him, that they took care of his body in a way not even the highly respected Spurs could, that they — and just about everyone else north of the border, really — treated him like royalty. Leonard was leaving, period. He was his famously quiet self, but others in his camp telegraphed his intentions clearly enough. Besides, the timing wasn’t right; he angled for the maximum contract possible, and the five-year, $190-million offer they had to put on the table eliminated any one-plus-one arrangements that could have coincided with the existing deals of other vital cogs.

The writing was on the wall. Why would Leonard eschew the opportunity to burn rubber close to sunny shorelines when re-upping with the Raptors for another half decade would mean just another year of contention? The likes of Kyle Lowry, Serge Ibaka, and Marc Gasol were all on expiring deals. Nonetheless, they gamely made their presentation. By all accounts, it was nothing short of outstanding. And, by all accounts, it didn’t produce the desired effect. They got the impression that he had already made up his mind.

Perhaps Leonard didn’t have the heart to tell the Raptors they were a poor third early on. Perhaps he didn’t want to; he needed them to keep having a skin in the game because of their role as motivators on a deal he was pushing for. Like the Clippers, they knew he wanted to play with Paul George, thusly requiring them to reach out to the Thunder for the latter’s availability. Unlike the Clippers, they didn’t receive any assurance that netting the six-time All-Star would net him as well. And as the bidding war grew to ridiculous proportions, Ujiri had no choice but to pull out.

Make no mistake. The Raptors would still have thumbed up the deal if they knew then what they know now. They’re defending champions of the NBA, and while they will most definitely not be this time next year, they will forever treasure their experience as the best of the best. How much it will actually cost them remains to be seen. After all, they did lose a piece of themselves in making winning their only priority. It’s why DeRozan continues to seethe. It’s why Leonard had no qualms leaving them and, worse, using them as pawns in order to get his way. And it’s why they’ll be hard-pressed to move on.

(Tomorrow: The Thunder, shell-shocked and yet fortunate.)

Anthony L. Cuaycong has been writing Courtside since BusinessWorld introduced a Sports section in 1994. He is a consultant on strategic planning, operations and Human Resources management, corporate communications, and business development.