The Toronto Raptors have struggled to gain their footing after entering a brief rebuild and changing over nearly their entire roster. Could the path forward actually mean bringing back a former player in a blockbuster trade?
Toronto has brought together a collection of players who are good on their own, better with the ball in their hands, and largely properly paid, if not slightly overpaid. They have a roster that fits together awkwardly and no obvious paths to everything settling into place outside of making a trade.
They aren't going to trade Scottie Barnes, and they just added Brandon Ingram and have yet to see him play a single game. Jakob Poeltl is not only overpaid but just signed a brand new extension to continue overpaying him for years to come. RJ Barrett is not a seamless fit on other teams and his value doesn't seem to be extremely high. The young up-and-comers don't make enough money to bring back a significant piece in a trade.
The best trade candidate on the roster might be Immanuel Quickley. He is likely also overpaid on his current contract, but is young enough for teams to think he can grow into it. He can shoot, something teams covet, and has utility to play on-ball or off-ball. Toronto may be wise to capitalize on any value he currently has if another team is interested in a trade -- not merely to trade Quickley, a player they like, but to find a pathway to adding another difference maker.
Enter the Houston Rockets and the newfound desperation.
The Rockets need a new point guard
The Houston Rockets have an unbalanced roster somewhat similar to the Raptors in that they have a plethora of frontcourt players and are relatively thin in the backcourt -- except Houston takes it to the extreme. It was recently announced that veteran point guard Fred VanVleet tore his ACL and will likely miss the entire season.
Houston has no one to replace him. They will try to put the ball into the hands of Amen Thompson more, and have skilled center Alperen Sengun handle the ball and make plays. Second-year guard Reed Sheppard will need to sink or swim with no safety net. And the question of where the shooting will come from in the rotation is an unanswered one.
The Rockets likely need to make a trade once restrictions lift in December, and if they want to maximize their current window and be a true contender this season, such a trade needs to be for a significant player. They could push in all of their chips and go after an All-Star guard, but there are no guarantees such a player is available.
Enter Immanuel Quickley and the Raptors. He can play on-ball and run the offense, or slide off-ball and space the floor alongside Thompson and Sengun. He is not a total liability on defense, which may be enough surrounded by the athleticism and defense the Rockets have. His contract is large, to be sure, but perhaps that's what makes him available.
Houston will need to match Quickley's salary, so trading Fred VanVleet in a deal makes sense. Yet he has an implicit no-trade clause because he could become a free agent next summer and lose his Bird Rights, which could limit trade partners. Would Toronto be one of the teams he would waive that no-trade for?
Building a VanVleet - Quickley trade
With all of that in mind, here is what a trade could look like:
The Rockets get Quickley to slot in as their starting point guard alongside Amen Thompson in the backcourt, and he can largely fill the same role as VanVleet -- without the veteran leadership and defensive tenacity, but it's something in the same realm. Houston also adds Jamal Shead, an inexpensive defense-first guard who can mix in alongside Aaron Holiday as the backup to Quickley.
The Raptors, on the other hand, make a play for the future. VanVleet is likely to opt into his player option for 2026-27, so he will essentially be dead salary for this season and then step into place next year in a prominent role. He showed in Houston that his play style and leadership can help to turn a team's culture around.
VanVleet is an aging small guard coming off of a major injury, so his trade value is somewhere around neutral at best. That's where Reed Sheppard comes in as the rest of Houston's matching salary. It would be difficult for them to move on from Sheppard this early into his career, but they are built to win now and Sheppard appears to need some time. The Raptors can give him that time, and by trading Quickley and Shead there will be a gaping hole at point guard for him to step into and get developmental minutes this year.
Sheppard's upside is All-Star, and Toronto can afford to be patient and see if that develops. If it does, they have a complement to Scottie Barnes and Brandon Ingram in the backcourt. It's a swing with risks, but it opens up their future financial flexibility and takes an upside swing on a talented prospect whose best skill is shooting. That's the kind of move the Raptors need to make.
If Houston comes calling, Sheppard is the player to ask for. This trade could be a massive win for the Raptors.