Why the Raptors Should Go All In for Damian Lillard

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Damian Lillard’s trade demand has created a tense standoff between himself, the Portland Trail Blazers, and the Miami Heat, which is reportedly the only organization he wants to play for. There are other teams with reported interest out there—the Clippers, Jazz, Nets, Sixers, Spurs, and Celtics, to name a few—but there’s one relatively under-the-radar suitor that makes as much sense as any other: the Raptors.

There are several trade package iterations that could work, including some more complicated ones that would rope in a third team, but here’s my favorite right now:

Raptors get: Damian Lillard, Nassir Little
Blazers get: Scottie Barnes, Gary Trent Jr., Chris Boucher, Thaddeus Young, Otto Porter Jr., Toronto’s unprotected first-round pick in 2028, and a pick swap in 2029

Let’s first look at it from Portland’s viewpoint. This is the best realistic trade offer the rebuilding Blazers can get for a 6-foot-2 33-year-old who’s guaranteed $58.5 million in 2026 and $63.2 million in 2027. It beats anything Miami or Philadelphia can currently put on the table, and beats the most sensible bundle of assets that Utah, Boston, or Brooklyn could bear to surrender.

Barnes is a season removed from winning Rookie of the Year and an ideal combination of talent, upside, and muscle next to Scoot Henderson and Shaedon Sharpe. He’s a 6-foot-8 shape-shifter who can guard all five positions, facilitate, obliterate smaller foes in the post, rebound in traffic, and, most importantly, positively impact areas of the game without the ball in his hands. Barnes is not Tyrese Maxey (a turbo-charged albeit undersized combo guard) or Tyler Herro (an expensive, one-dimensional gunner). Neither makes sense on the Blazers, which is partially why this stalemate exists.

Barnes’s statistics plateaued during a disappointing sophomore season during which his 3-point percentage dipped to a grim 28.1 percent, but this is still a culture-setting prospect who has All-NBA feasibility—an unselfish athlete with touch, footwork, and preternatural instincts. If you’re Blazers GM Joe Cronin, the immediate response if/when Scottie’s name ever comes up in a conversation with Raptors brass is “Yes, please.”

It’s not that Toronto is an inconvenient city for Barnes to fully develop his game, but Portland can provide a fresher canvas and longer runway. Additionally, getting a bunch of expiring deals, Boucher’s flippable contract, an unprotected first-round pick, and what could be a very valuable pick swap makes obvious sense.

Now, all that was just written is why this trade is so controversial. You might be asking yourself: Why would the Raptors exchange an inexpensive blue-chipper with limitless potential for someone a full decade older who’s going to make a lot of money over the next four years?

For some reasonable people, this isn’t even a question. Toronto hangs up the phone without hesitation. But for those who see a front office that clearly doesn’t want to tank, this trade is an opportunity for Masai Ujiri to clarify Toronto’s trajectory in a neat, convenient, irresistible way. After losing Fred VanVleet for nothing, there aren’t many solutions better than “add Damian Lillard without losing my best player or all my tradable draft picks.”

Moving Pascal Siakam is no longer necessary. Toronto’s star forward is about to enter the final season of his contract. Suddenly, with Lillard in tow, re-signing him to a long-term deal is a no-brainer. Worrying about an overpay for O.G. Anunoby becomes irrelevant when you’re all in, too.

The timeline would peel down. The path would be set. Lillard fills the superduperstar vacuum that Kawhi Leonard’s departure created in 2019. Conveniently enough, on the Raptors, Lillard would also slide onto a roster that ameliorates some of his most visible shortcomings. Anunoby and Siakam are perfect as long, versatile wing defenders who can ease his burden on the defensive end and diversify how Toronto wants to attack. Jakob Poeltl makes perfect sense, too, as a trustworthy pick-and-roll partner and sturdy rim protector.

Dennis Schröder can fall back into a more logical role as one of the league’s peskier and most potent backup point guards. Jalen McDaniels, Precious Achiuwa, Christian Koloko, and Little are not to be dismissed, and should Gradey Dick’s shooting enter the equation, all the better.

The price tag for all of this would be hard to swallow, especially with the increased leverage Anunoby and Siakam would have negotiating their next deals. But if Lillard looks anything like he did last season (which was the best of his career) over the next few years, the Raptors could vault into contention, able to compete with and even beat Milwaukee, Philadelphia, Boston, and Cleveland. (Miami would be in significant trouble if this trade actually happened.) More win-now trades can always happen, too.

The Raptors might think they can stay the course and hope that Barnes makes a traditional third-year leap and eventually anchors a roster that’s built around his all-around brilliance. There’d be no real sacrifice adopting that plan, and it’d align with a belief held by some around the NBA that last year’s league-wide plunge into parity is a new normal. The gap between the haves and have-nots may no longer be uncrossable in a seven-game series, as the Heat just showed on their play-in-to-Finals run. It’s an idea exacerbated by the new CBA. Look at the Celtics’ unwillingness to keep Grant Williams because doing so would’ve pushed them across the second apron. Same goes for Miami with Gabe Vincent and Max Strus. The Warriors with Jordan Poole. Even the Hawks and John Collins. Juggernauts cannot weather this economic environment.

But even if that is Ujiri’s train of thought, isn’t it all the more reason to get Lillard? As a team that just lost its star point guard but also went a respectable 15-11 after landing Poeltl at the trade deadline, this blockbuster can position Toronto near the top of the pack in the East, elevated above the conference’s striving class. Why not take a chance on someone who was last seen averaging 32.2 points on a boiling 64.5 true shooting percentage, and finished first overall in offensive estimated plus-minus?

Lillard only wants to play for the Heat, and his representatives are trying to steer every other interested team away by claiming he’d be unhappy enough not to report. That’s obviously not going to happen. Lillard is under contract for four more years, and if winning the title is his goal, this hypothetical Raptors team could be just as good as Miami—depending on how much exactly the Heat would have to give up to get him. They just made the Finals but would be down Strus, Vincent, Victor Oladipo, Tyler Herro, (probably) Duncan Robinson, draft capital, and a young prospect or two. Jimmy Butler will turn 34 in September. Kyle Lowry will be 38 next season.

Nothing is certain in the NBA. Barnes might forever be limited by his iffy outside shot. Lillard’s body could start to crumble sooner rather than later. But if Ujiri wants to make another Finals appearance anytime soon, it’ll take bold rationale. Swapping DeMar DeRozan for a season of Kawhi was always less risky than some made it seem, but it was risky nonetheless. The Raptors have won only one playoff series since that championship. Why shouldn’t we expect another shocking move to set them back on track?

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