Damian Lillard would just be the marquee player on another middle-of-the-pack team if traded to Toronto

A decade of experience indicates that Toronto Raptors president Masai Ujiri despises rebuilding. This became immediately apparent after he refused to tank for Andrew Wiggins back when he was still being referred to unironically as Canada’s “Maple Jordan” before the 2013-14 season. After watching the Raptors get eliminated in the play-in, canning Nick Nurse, and allowing Fred Van Vleet to walk in free agency, the mise-en-scène was in place for Toronto’s first real demolition project of the Ujiri era. However, at his end-of-season State of the Raptors address, he nixed that idea.

“I never look at the last 10 years,” Ujiri bemoaned about rebuilding. “All I think about is how you win. I always think that sometimes we have to validate the championship we won. That’s how much we have to win here. And I believe that we’re going to win again in Toronto. I feel strongly about that… we are about winning. We’ve not only said it, we’ve at least tried to do it. That’s where we’re going to continue to go.”

After a quiet offseason, Ujiri is boldly attempting to follow through on his promise. The Raptors are invested in negotiating with Portland for a Damian Lillard trade. Yet, Dame Lillard wants to be in Miami by hell or high water. These contradictory forces are about to converge. At the bare minimum, it’s plainly clear Lillard is not interested in being the marquee player on another middle-of-the-pack team. Being Steph Curry’s vassal for a decade has clearly done a number on him.

Any deal that takes place would involve Toronto’s All-Defense forward OG Anunoby and Gradey Dick. The irony is that a swap with Toronto for Anunoby’s expiring contract and Dick (it’s going to take a while to get that phrasing down without it being awkward) is that it would give the Trailblazers the type of young, versatile, switch-heavy lineup Lillard needed five years ago.

However, Ujiri is more Pat Riley than Sam Presti, the author of Oklahoma City’s rebuild. In many ways, Toronto resembles the pre-Jimmy Butler Miami Heat four years ago. Riley’s Heat were a gritty, stellar defensive team, who’d just labored through Dwyane Wade’s farewell season and were in search of a spark without possessing a paradigm-shifting lottery pick. While Butler lifted the Heat’s trajectory, nobody expected the 30-year-old forward to carry them to a pair of Finals in his debut season.

Toronto showers its star players with hero worship, but will Lillard love them back? If Lillard were younger than 30, this would be a more intriguing fit, but the Raptors have three years max to squeeze a title out of this group before the sand runs out of Dame Time’s hourglass. But acquiring Lillard is the ultimate example of Ujiri’s faith in himself. The Raptors’ modus operandi is to accumulate assets, draft well, and execute shrewd trades. The Raptors averted a rebuild around DeMar DeRozan by pairing him with Kyle Lowry, who was obtained early in his career for a protected first-rounder and forward Gary Forbes.

Kawhi Leonard’s trade to Toronto worked for both parties because he was in his pre-agency year and this was a chance to reboot his career with a contender and then take the circuitous route to his preferred destination in Los Angeles.

Toronto has never shaken up the league through free agency. The metaphysical distance for most American-born pros with options between franchises in major markets and Toronto might as well be interstellar travel. Few volunteer for the journey. Van Vleet is still the only free agent signing in Raptors franchise history to make an All-Star game while signed with them and he was an undrafted rookie at the time. Nigeria-born Hakeem Olajuwon made the leap for his 18th season as the consolation prize for the departed Trace McGrady, but The Dream was a shell of himself by then. Maybe Ujiri is counting on Olajuwon feeding Antetokounmpo Toronto propaganda as well as footwork lessons between the post move sessions they’ve been conducting all summer.

It would be one thing if Scottie Barnes hadn’t just regressed miserably. Barnes’ third season will be the barometer for whether he hit his peak earlier than his fellow rooks or if his upside has some bounce on the other side of his Rookie of the Year award. As for Lillard, he slots in nicely at the point guard spot vacated by Van Vleet. However, a significant upgrade from the beloved Van Vleet does not make Toronto the Next Miami Heat. The dream of flipping a few young pieces like Anunoby, Gradey Dick, and salary cap flotsam to match Lillard’s $45.6 million salary and replicating the 2019 Raptors championship magic is farfetched.

There is a slim path to making this work. Even with Lillard’s exorbitant contract, the Raptors would have the salary cap flexibility to make a move on the next disgruntled superstar to ask out whether it’s Giannis Antetokounmpo or Joel Embiid. Pascal Siakam is a fringe All-Star and an ideal No. 2, who has likely peaked, but Barnes is the missing piece. Unfortunately, unless another cornerstone top-10 player is seeking a Canadian work visa by the trade deadline, this could blow up in everyone’s faces if the Raptors are hovering around the play-in.

Follow DJ Dunson on X: @cerebralsportex