Alright ladies and gents, the other day I wrote about Portland taking an important hit to their roster. Specifically, it was reported that Shaedon Sharpe suffered a torn meniscus and is expected to miss six months. The first angle I immediately considered in the aftermath was how this likely complicates the Raptors’ path to an intriguing Jrue Holiday acquisition. Like the other trending guard target dominating recent Raptors chatter (that being Kyrie Irving), Holiday would give Toronto a championship-proven vet to help run the floor in their hopeful push for another title.
While the route to adding Holiday still looks pretty bleak and mellow at the moment, Sharpe’s injury sparked another idea for me to explore. It’s a logical footpath for Toronto — one that not only addresses a key issue staring them in the face but also benefits the Blazers in their time of need. And finally, it could help them land Jrue Holiday in the process.
The trail to get there (pun intended) starts with RJ Barrett. Despite his feel-good coming-out party in the 2026 playoffs, where he silenced many critics and proved to be a crucial contributor for a gritty Raptors squad — there’s still a lingering sense of uncertainty about the 26-year-old’s future with his hometown team.
Barrett will head into the upcoming 2026-27 season on his expiring $29.6 million contract, facing a slightly revamped Raptors roster that’s expected to see Kawhi Leonard rejoin the Six once that trade finally goes through. He’s been extension-eligible for a while now, but it seems both sides haven’t yet come to an agreement on a new deal. It’s also not entirely clear if the Raptors’ front office truly envisions the Maple Mamba as a core pillar moving forward. Plus, once Leonard’s trade is finalized, it’ll likely lead to another extension for the superstar forward — further limiting the Raptors’ already tight financial resources.
The Raptors have made some questionable financial decisions in the past, with extensions for Immanuel Quickley and Jakob Poeltl standing out as relatively weak moves on Toronto’s financial front, so their patience could just be a sign of Toronto learning from their prior mistakes. Although I wouldn’t completely rule out that scenario, I still think it mostly comes down to the organization being on the fence about Barrett’s long-term fit and whether it makes sense to lock him in financially with this core. He’d probably take a backseat going forward, compared to the key role he’s been holding since arriving in Toronto, and questions of how effective he can be off the bench or in a lesser role have been subjects of debate.
Here’s where the Blazers come in.
Raptors and Blazers could be suitable trade partners after the Shaedon Sharpe injury
I’m not saying that you can perfectly replace Shaedon Sharpe by slotting RJ Barrett in his place, but I can definitely see a world where the Maple Mamba fits with what Portland is building. While all signs point to the Blazers aiming to be a dark horse in the West (given their Ja Morant splash, Damian Lillard’s return, and their young core’s development) — there’s still a likely outcome where Portland remains a mid-to-late playoff team, hovering around the play-in.
Their bold idea to run a Dame-Ja backcourt has raised eyebrows across basketball circles, and I could easily see a scenario where the Blazers are left scrambling to fix the kinks and pivot to a different strategy. That’s where someone like Shaedon Sharpe could’ve been a solid plan B, but they’ll need to wait a bit before he’s back to game speed. Enter RJ Barrett, who could help fill some of those gaps. Barrett can step in as a high-volume scoring wing for the Blazers, and at just 26, he still has youth on his side — giving Portland the freedom to decide if he’s someone worth keeping long-term, especially if their immediate plans with the Ja-Dame experiment fall short.
One could argue that Jrue Holiday’s veteran status is the Blazers’ missing link to use here instead, but I’d much rather see his remaining NBA years defined as a valuable floor general for Toronto, rather than taking a backseat in Portland behind Lillard and Morant. Dame is one of my all-time favorites, but coming off a torn Achilles and at age 36, I think he’d be better suited coming off the bench as that instant scoring spark and proven floor spacer. And as a result, if the Blazers opt for a usual starting lineup of, say, Ja-Barrett-Avdija-Camara-Clingan — that isn’t too shabby at all.
Sure, the big questions about spacing and offensive flow for Portland would still linger after the RJ trade. But think of this as a sort of rental and audition process for Barrett with the Blazers. When Sharpe returns, it gives the Blazers more flexibility in their depth, allowing them to experiment with lineups as needed.
Also, RJ’s expiring salary gives Portland a bit of relief compared to Holiday’s remaining $72 million salary for two more years. From the Raptors’ side, that doesn’t look especially great given their tight financial situation, but they were always going to have to make a decision with Barrett — either let him walk for nothing, extend him, or trade him to recoup some value. This situation would likely open the door for Immanuel Quickley to step into the shooting guard spot alongside Jrue Holiday in the backcourt. That pairing, combined with the rest of the starters (Leonard, Barnes, and Jakob Poeltl/or CMB) offers a more natural fit than trying to slot Barrett into the starting shooting guard role, given how things stand right now.
You could just do a straight-up swap, toss in some draft capital to spice things up, or, as I played around with in the trade machine: send Barrett and Trayce Jackson-Davis to Portland for Jrue Holiday and Vit Krejci (a sneaky pickup who could give Toronto solid bench minutes and shooting upside).
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