Why the Raptors should go all-in for Damian Lillard

Damian Lillard’s trade demand has created a tense battle between himself, the Portland Trail Blazers and the Miami Heat, who are 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: the Raptors .

There are several iterations of the trade package that could work, including some more complicated ones that would secure 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 2028 unprotected first-round pick and a 2029 pick trade

First, let’s look at it from Portland’s point of view. This is the best realistic trade offer the rebuilding Blazers can get for a 33-year-old 6-foot-2 guaranteed $58.5 million in 2026 and $63.2 million in 2027. That beats anything Miami or Philadelphia currently have can put on the table, and beats the most reasonable 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 is a 6-foot-8 shape-shifter who can guard all five positions, facilitate, wipe out smaller enemies on the post, rebound in traffic and, most importantly, positively influence areas of the game without the ball in the hands. Barnes is not Tyrese Maxey (a turbocharged if undersized combo guard) or Tyler Herro (an expensive, one-dimensional shooter). Neither makes sense on the Blazers, which is partly why this impasse exists.

Barnes’ stats dipped during a disappointing sophomore season in which his 3-point percentage dipped to a dismal 28.1 percent, but this is still a culture-making prospect who has All-NBA feasibility — an unselfish athlete with touch, footwork and supernatural instincts. If you’re Blazers GM Joe Cronin, the immediate response if/when Scottie’s name ever comes up in 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 could provide a fresher canvas and longer runway. Plus, you get a bunch of expiring deals, Boucher’s flippable contract, an unprotected first-round pick, and what could be a much 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 trade a cheap blue-chipper with unlimited potential for someone a full decade older who is going to make a lot money over the next four years?

For some sane people, this isn’t even a question. Toronto hangs up without hesitation. But for those who see a front office that clearly doesn’t want to go out on a limb, this trade is an opportunity for Masai Ujiri to clear Toronto’s pitch in a nice, convenient and 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 of my tradeable draft picks.”

It is no longer necessary to move Pascal Siakam. Toronto’s star forward is entering 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 overpayment to OG Anunoby becomes irrelevant when you are also all in.

The timeline would peel down. The path would be set. Lillard fills the super-duperstar vacuum that Kawhi Leonard’s departure created in 2019. Conveniently, Lillard on the Raptors would also slide onto a roster that addresses some of his most visible flaws. Anunoby and Siakam are perfect as long, versatile wing defenders who can lighten the load on the defensive end and diversify how Toronto wants to attack. Jakob Poeltl also makes perfect sense as a reliable pick-and-roll partner and rugged rim protector.

Dennis Schröder can fall back into a more logical role as one of the league’s more annoying 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 to negotiate 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 launch themselves 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 may think they can stay the course and hope Barnes makes a traditional third-year leap and eventually anchors a roster built around his all-around brilliance. There would be no real sacrifice in adopting that plan, and it would align with a belief held by some in the NBA that last year’s league-wide dip in parity is a new normal. The gap between the haves and the have-nots may no longer be insurmountable in a seven-game streak, as the Heat have just shown on their play-in-to-the-Finals run. It’s an idea exacerbated by the new CBA. Look at the Celtics’ unwillingness to keep Grant Williams because that would have pushed them over the second apron. The same goes for Miami with Gabe Vincent and Max Strus. The Warriors with Jordan Poole. Even the Hawks and John Collins. Juggernauts cannot handle this economic environment.

But even if that’s Ujiri’s thinking, isn’t that 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 could put Toronto near the top of the pack in the East, above the conference’s struggling class. Why not take a chance on someone who was last seen averaging 32.2 points on a blistering 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 away any other interested teams by claiming he would 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 as good as Miami — depending on how much 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 turns 34 in September. Kyle Lowry will be 38 next season.

Nothing is certain in the NBA. Barnes may forever be limited by his iffy outside shot. Lillard’s body could start to crumble sooner rather than later. But if Ujiri wants to appear again in the finals soon, it will require a bold justification. Trading DeMar DeRozan for a season of Kawhi was always less risky than some made it out to be, but it was risky nonetheless. The Raptors have won just one playoff series since that championship. Why shouldn’t we expect another shocking move to put them back on track?

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