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Raptors’ interest in Lillard is real but ‘overstated’

Damian Lillard Portland Trail Blazers Damian Lillard - The Canadian Press

TORONTO – The Raptors have long been preparing for the chance to bid on a transcendent, franchise-altering star, the type of player capable of lifting them out of mediocrity and completely shifting the balance of power in the Eastern Conference and perhaps across the NBA landscape.

They did it once before and have a championship to show for it, so you can understand why they might be inclined to take the plunge again.

They’ve repeatedly resisted external pressure to pivot in a different direction and take themselves out of the running for such an opportunity. When rival executives expected them to dismantle their veteran core amid a disappointing season, they added to it. After losing a key member of that core in free agency, they opted for status quo. They’ve prioritized flexibility and remained patient, arguably too patient, but to what end? That’s a pretty open secret.

“At the end of the season there’s always a player that wants to move or wants [a] change and that’s the new free agency, basically,” Raptors president Masai Ujiri said ahead of what’s turned out to be a busy but underwhelming – to this point, at least – offseason. “Free agency doesn’t happen anyway, really. The new free agency is players [changing] teams.”

When Kevin Durant decided he had enough of the sideshow in Brooklyn last summer, Ujiri and the Raptors were in the mix. They kicked the tires on Rudy Gobert and Donovan Mitchell before Utah sent them to Minnesota and Cleveland, respectively, though those discussions never got past the preliminary stage. They checked in on Bradley Beal, though his no-trade clause complicated things, and like Durant, he ultimately forced his way to Phoenix.

This is a front office that isn’t afraid to go big-game hunting but one that’s still waiting for the right catch. Might that be Damian Lillard, the NBA’s latest disgruntled star?

As multiple sources confirmed to TSN, the Raptors’ interest in Portland’s all-star guard is real, albeit “a bit overstated at this point.”

The Trail Blazers have been operating with minimal leverage since Lillard and his representatives went public with their trade demand and list of preferred destinations, which is limited to one team: Miami. With the start of training camp fast approaching, this sudden uptick of teams reportedly registering interest could simply be the result of Portland feeling the heat – no pun intended – and trying to take some of that leverage back, as one source suggested.

If the Heat, or any other team, had hoped to slow play a negotiation and swoop in with anything less than their best offer, they might have to think twice – or at least that’s what the Blazers are hoping for. Whether the Raptors are “frontrunners”, “dark horses” or “contenders” in the Lillard sweepstakes is a moot point for now. Take all these distinctions and the myriad of teams that will be mentioned between now and whenever he ends up getting traded with a grain of salt.

But yes, the Raptors like Lillard. They have for some time. The previous regime had the Weber State product ranked just below Anthony Davis atop their draft board in 2012 – a season in which then general manager Bryan Colangelo admittedly tried to tank. If not for a Game 82 win over the Nets, a team they were competing with for lottery balls, they may have been in a position to select him sixth overall (instead, they took Terrence Ross with the eighth pick). Toronto’s current front office has long admired the seven-time all-star as well; it’s kept a close eye on his deteriorating relationship with the Blazers, the only NBA franchise he’s ever known.

A proven closer, lethal outside shooter and one of the league’s best offensive creators in the half court, Lillard would address some glaring long-time needs in Toronto, while playing a position of need in the aftermath of Fred VanVleet’s departure. But the veteran point guard also comes with at least a few red flags worth considering.

Lillard is not exactly known for his work on the defensive end, he has an extensive injury history, just turned 33 and is owed north of $215 million over the next four seasons. Then there’s the not-so-small matter of whether he can be sold on a long-term future in Toronto, or if he would even show up. That’s not likely to be a deal breaker for a Raptors team that took a similar gamble in 2018 when they traded for Kawhi Leonard, who was famously pining for a Los Angeles homecoming. Unlike Leonard, whose tenure came to a predictable end after one historic campaign in Toronto, Lillard is under guaranteed contract for at least three more seasons. Still, acquiring him is not without its risks. For Ujiri and GM Bobby Webster to pull the trigger, those risks would almost certainly need to be baked into the cost, like they were in the Leonard deal.

The Raptors balked at the idea of including Scottie Barnes in a trade for Durant last summer, and even after a so-so sophomore season, the belief is that he remains off limits. At 29, Pascal Siakam doesn’t seem like a fit for the Blazers, who are said to be targeting draft picks and rising stars to pair with their promising young guards, rookie third-overall selection Scoot Henderson and electric Canadian Shaedon Sharpe.

The most plausible trade package would likely centre on O.G. Anunoby and could include former Trail Blazer Gary Trent Jr., rookie Gradey Dick, salary filler, as well as multiple first-round picks (first, Toronto would need to lift the protections on the 2024 pick it sent to San Antonio in the deadline-day deal for Jakob Poeltl last February).

Would that be enough to hold off Miami and satisfy Portland’s asking price? Is that too steep for Toronto? Remember, the Raptors would need to feel confident that they’d still have enough talent around Lillard to contend over the next few years, and given their current lack of organizational depth and Anunoby’s utility as a reliable shooter and all-world defender, that’s no certainty. There’s also the opportunity cost associated with any all-in scenario. Once you’ve consolidated your assets and pushed your chips in, you can’t do it again. When the NBA’s next disgruntled star inevitably becomes available, they would be spectators.

The Raptors have been waiting for an opportunity like this, but that doesn’t necessarily mean that this is the right opportunity, the right time, or the right player. Is Lillard the guy that takes them to the next level? As players reconvene at OVO Centre in Toronto this week ahead of training camp, which is set to open in Vancouver next Tuesday, Ujiri and Webster are busy asking themselves that question. And if Portland’s urgency to get a deal done and the recent influx of league-wide interest are to be believed, they don’t have much time to figure it out.