The Toronto Raptors' on-court hierarchy came together at a Bay Area restaurant during the 2017 NBA Finals and reached a defining moment in their partnership.
Then-coach Dwane Casey made the pitch to DeMar DeRozan and Kyle Lowry in that meeting: No more iso-ball. No more mid-range. In order for the Raptors to double down on their head coach and core, they had to space the floor and share the ball.
A few months later, DeRozan was called into the principal's office—that of team president Masai Ujiri. DeRozan later told ESPN.com's Zach Lowe that when he was summoned to the meeting—which also included general manager Bobby Webster and the team's three highest-ranking coaches—he thought he was getting traded. Actually, the point of the meeting was to talk DeRozan into shooting more threes.
After a 59-win season went down in flames with another embarrassing playoff sweep at the hands of LeBron James, the outcome that DeRozan had feared back in December finally happened Wednesday. A four-time All-Star, DeRozan was shipped to the San Antonio Spurs along with Jakob Poeltl and a heavily protected 2019 first-round pick for Kawhi Leonard and Danny Green.
And thus, the Raptors are now front and center in the NBA's new high-stakes free-agent recruiting game: the one in which you trade for an impending free agent and then spend an entire season recruiting him to stay.
"They're doing the Paul George thing," a prominent agent told Bleacher Report on Wednesday. "They're taking a calculated risk."
But in the estimation of multiple agents and rival team executives who spoke with B/R on the condition of anonymity, it's a relatively low-risk move for the Raptors.
On one hand, it had become abundantly clear that Toronto wasn't going anywhere with the DeRozan-Lowry backcourt. Add in that it was widely known that Leonard wanted out of San Antonio, and the opportunity presented itself for Ujiri to shake up the roster and get a two-time Defensive Player of the Year to build around—while giving up only one expendable All-Star in the process.
Still, there's a risk involved—a very real one, said two league sources who believe Leonard is hellbent on signing with the Lakers as a free agent next summer. Ujiri, who was in Kenya on Wednesday and unavailable for comment, will spearhead the Raptors' year-long courtship of Leonard in hopes of persuading him to trust his vision, become the face of the only NBA franchise in Canada and re-sign for five years and $190 million next summer.
The Lakers would only be able to offer a four-year deal for $141 million, though they could also offer Leonard the opportunity to play in his hometown of Los Angeles and team up with James.
This trend of trading for a prospective free agent and recruiting him on your own turf and terms began in earnest in 2011, when the Clippers acquired Chris Paul from New Orleans. Paul twice re-signed with the Clippers before forcing his way to Houston in a blockbuster trade last summer.
But the biggest coup was pulled off by the Oklahoma City Thunder, who acquired George from Indiana last July with only one year left on his contract before he hit free agency. Thunder GM Sam Presti and coach Billy Donovan spent the past year selling George on their franchise and vision—not to mention stroking his ego. In a stunner, George decided to re-sign with the Thunder this summer on a four-year, $137 million deal.
"Who would've thought Paul George would stay in Oklahoma City?" the prominent agent said. "And Toronto is a way better city. Not even close."
While Leonard is figuring out whether he wants to be the King of Canada or play with the King in L.A., Ujiri holds a trump card. A couple of them, actually.
As Lowe notes, if the Raptors get a strong feeling that Leonard is L.A.-bound, they could always trade him somewhere else at the February deadline—recouping enough of what they gave up to justify the gamble.
Also, since Ujiri took over the Raptors' basketball operations in 2013, his desire has always been to remake the organization in his desired image. But his ill-fated deal to send Lowry to the Knicks in 2013—nixed by Madison Square Garden chairman James Dolan, according to Jeff Zillgitt of USA Today—derailed those rebuilding plans. The Raptors kept winning, and Ujiri kept doubling down on Casey and the core assembled by former executive Bryan Colangelo.
Until this summer. Starting with the firing of Casey—who later was named NBA Coach of the Year—and now with the blockbuster deal for Leonard, Ujiri has, at long last, begun the inevitable process of putting his stamp on the franchise.
"There's no risk for Masai," a Western Conference GM told B/R. "It's a splashy move for a temporary win with upside. If it doesn't work, they go into a rebuild, which is what he wanted to do when he took over."
After watching their relationship with Leonard deteriorate to the point of no return this past season, the Spurs had no choice but to move him. It's a crossroads for the NBA's model organization, which saw Tony Parker sign with Charlotte and now awaits clarity on how much longer Gregg Popovich will be roaming the sidelines. Considering their diminished leverage, the Spurs could've done worse than land a four-time All-Star in the deal.
The trade is a clear-cut win for the Raptors, too—at least in the short term, as long as Leonard is healthy enough to regain his status as a top-five player in the league. But even if Toronto loses in the long run—even if Leonard is true to all the buzz surrounding him and bolts for the Lakers next summer—it was a risk worth taking.
And while there will be a lot of teams with max dollars to throw at Leonard next summer—including the Lakers—there's only one team that will have an entire year to recruit him, every single day. And it just so happens to be the only team in Canada.
"It's a big market, but it's not super big," the prominent agent said. "So to me, that fits Kawhi's personality."
In a little less than 12 months, we'll know if that's true. In the meantime, for one team at a distinct tipping point in its existence, the recruitment of Kawhi Leonard has begun.
Ken Berger covers the NBA for Bleacher Report. Follow him on Twitter:@KBergNBA.