Shaedon Sharpe’s torn meniscus and expected six-month absence has already started to ripple beyond Portland, and one of the clearest dominoes could land in Toronto.
The immediate thought after the injury was simple enough: it makes the Raptors’ path to a Jrue Holiday deal tougher. Holiday has been one of the bigger guard names tied to Toronto lately, right alongside Kyrie Irving, and he’d bring the kind of championship-tested presence the Raptors would want if they’re serious about another title run.
But Sharpe’s setback also opens another lane for the Raptors, one that could help solve a real roster question while giving the Blazers a useful short-term answer. That route starts with RJ Barrett.
Barrett’s 2026 playoff run changed the conversation around him. He had a strong coming-out party, quieted plenty of critics, and became an important piece for a tough Raptors group. Even so, there’s still uncertainty about where he fits long term in Toronto.
He’s heading into the 2026-27 season on an expiring $29.6 million deal, and the Raptors are expected to bring Kawhi Leonard back once that trade finally gets completed. Barrett has been extension-eligible for some time, but no new deal is in place yet.
It also isn’t clear whether Toronto’s front office sees him as part of the core going forward. And once Leonard’s trade is finalized, another extension for the superstar forward would only tighten the team’s already limited financial room.
Toronto has already made some shaky money decisions, with the extensions for Immanuel Quickley and Jakob Poeltl standing out as weak spots on the ledger. So the hesitation with Barrett could be a sign the team is trying to be more careful this time.
Even so, the bigger issue seems to be whether Barrett truly fits the long-term plan, especially if his role shrinks in a lineup built around Leonard and the rest of the current core. Questions about how he’d handle a lesser role, or even a bench assignment, have been part of the discussion.
That’s where Portland enters the picture.
Sharpe’s injury doesn’t mean Barrett can simply replace him like-for-like, but there’s a real case that he could make sense for what the Blazers are trying to build. Portland has made a splash with the Ja Morant move and Damian Lillard’s return, while also leaning on its young talent. That said, there’s still a very real path where the Blazers settle in as more of a mid-to-late playoff team, somewhere in the play-in mix.
The idea of a Dame-Ja backcourt has already turned heads, and it wouldn’t be shocking if Portland eventually has to adjust once the reality of the roster sets in. Sharpe could have been a useful backup plan, but with him sidelined for a while, Barrett becomes a plausible fill-in. He’d give the Blazers a high-volume scoring wing, and at 26, he still has enough runway for Portland to decide whether he’s worth keeping beyond this stretch.
Holiday, by contrast, may be a better fit for Toronto’s side of the equation. There’s an argument that Portland needs his veteran stability, but the remaining years of his career feel more valuable in a Toronto role than in Portland, where he’d be behind Lillard and Morant.
Lillard is one of the league’s greats, but coming off a torn Achilles and at 36, he might be better used as an instant scoring burst off the bench rather than a primary option. A starting group of Ja, Barrett, Avdija, Camara, and Clingan would at least give Portland something workable.
There would still be real concerns about spacing and offensive flow if Barrett ended up in Portland. But the move would function as a kind of rental and audition, especially with Sharpe eventually returning and giving the Blazers more lineup flexibility.
Barrett’s expiring salary also matters. It gives Portland more breathing room than taking on Holiday’s remaining $72 million over two more years. Toronto wouldn’t love that part, given its own financial squeeze, but the Raptors were always going to have to decide what Barrett was worth: extend him, let him walk, or trade him before getting nothing back.
In that scenario, Toronto could also clear the way for Immanuel Quickley to slide into the shooting guard spot next to Holiday. That would create a cleaner fit alongside Leonard, Barnes, and Jakob Poeltl or CMB than trying to force Barrett into the starting two-guard role.
A straight-up swap is one possibility, and draft capital could be added to sweeten it. Another version, using the trade machine idea floated here, would send Barrett and Trayce Jackson-Davis to Portland for Jrue Holiday and Vit Krejci, giving Toronto a useful bench shooter and another body with some offensive upside.
In Other News...
Raptors Are Facing An Ugly Reality With Immanuel Quickley
The market around young, talented guards and wings has started to look a lot friendlier for teams than it did when Toronto made its big bet on Immanuel Quickley. Around the league, Bennedict Mathurin is headed to New Orleans on a two-year, $16 million deal with a player option for the second season, while Jonathan Kuminga is reportedly on his way to Minnesota on a two-year, $13 million pact with the same kind of flexibility. Those are the kinds of short-term numbers that can make front offices breathe easier, especially when a player is still proving where he fits.
For the Raptors, though, the timing only sharpens the pressure around Quickleys place in the roster picture. Toronto already committed to him on a much larger deal, and every new bargain elsewhere invites the same uncomfortable question about how much upside a team should pay for before it becomes expensive to wait. It leaves the Raptors in a spot where they need Quickley to look more like a cornerstone than a cost, because the league is providing plenty of reminders that not every promising young player has to be priced like one. [Read more 🡒]
Raptors Face A Brutal New Problem Against The NBA's Best
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Rajakovic said the Raptors can only do so much against players of that caliber, especially when a matchup tilts toward a teammate-dependent effort instead of a clean one-on-one solution. He also noted the ripple effect of James moving to the Eastern Conference with the Philadelphia 76ers, a change that could only make Torontos path through the East more complicated if the veteran forward remains anywhere near his usual level. [Read more 🡒]
Kyle Lowrys Long-Awaited Raptors Honor Gives Fans A Must-Watch Date
Kyle Lowry is finally set to get the kind of Raptors salute that has felt overdue for years. During the upcoming season, Toronto will raise his No. 7 into the rafters, a fitting tribute for a player who helped define the franchises most successful era and left behind a rsum that still sits near the top of the team record book in assists, steals and three-point field goals made. For a player whose edge and toughness became part of the Raptors identity, the ceremony figures to be one of the seasons biggest emotional nights.
The timing only adds to the intrigue, with the celebration coming in a game that carries a built-in storyline for Lowry and the fan base. He arrived as a title-chasing leader and left as one of the most important figures in franchise history, a central force in the 2019 championship run and a player whose impact stretched well beyond the box score. Toronto is giving supporters a chance to relive that run in a setting that should feel personal, and there may be another special touch attached to the night as well. [Read more 🡒]