Raptors Proposed to Trade Immanuel Quickley for 2x NBA Champion Star PG

Toronto Raptors v Houston Rockets
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HOUSTON, TEXAS - FEBRUARY 09: Immanuel Quickley #5 of the Toronto Raptors handles the ball against the Houston Rockets during the second half at Toyota Center on February 09, 2025 in Houston, Texas. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Alex Slitz/Getty Images)

While the Toronto Raptors wait for the Kawhi Leonard saga to come to a head, they can explore ways to add more talent to the roster. 

The Raptors are coming off a promising season, one that ended in a Game 7 against the Cleveland Cavaliers, an eventual Eastern Conference finalist. With Leonard (hopefully) now in the mix, Toronto’s ceiling is suddenly much higher. Then one considers what the franchise could be capable of if its many young players take another step in their development next season, particularly standout young swingmen Scottie Barnes and Collin Murray-Boyles

The decision to trade for Leonard meant one thing for Toronto: its championship window is open. If Leonard lands in Toronto, the team will have added one two-time champion. 

Why not one more? 


The Raptors Go All-In on Winning a Title By Adding This Two-Time Champ

Los Angeles Lakers v Portland Trail Blazers
GettyPORTLAND, OREGON – NOVEMBER 03: Jrue Holiday #5 of the Portland Trail Blazers looks on against the Los Angeles Lakers at Moda Center on November 03, 2025 in Portland, Oregon. (Photo by Steph Chambers/Getty Images)

As Sports Illustrated’s Raptors reporter Jeremy Brenner notes, the time for the Raptors to win is now.

“The next Leonard years for the Raptors are going to be crucial. The team hopes to sign him to a contract extension that will keep him in Toronto for the rest of his career, however long that may be. That being said, teams that are winning championships are not led by someone in their thirties. Usually, it is someone in their twenties.”

If Toronto doesn’t think it can win a title in the next two seasons, trading for Leonard, 35, is quite frankly useless. But the Raptors see the vision. They can see the man who led them to the mountaintop seven years ago do it again. But there’s one trade Toronto can make that would instantly boost its short-term title odds. And it’s for Portland Trail Blazers star Jrue Holiday.

Here’s a proposed trade that could land Holiday in Toronto alongside Leonard and the crew. 

Raptors receive: Jrue Holiday

Blazers receive: Naz Reid and a 2029 second round pick (via TOR)

Hornets receive: Immanuel Quickley

In this hypothetical trade, the Raptors land another title-driving piece in Holiday, a two-time championship, alongside Leonard and the rapidly-acsending Barnes. 


Would Portland Move Holiday?

Strictly looking at things in the short-term, Holiday is a considerable upgrade over Quickley. The 36-year-old Blazers star remains one of the league’s most terrorizing perimeter defenders and even showed again last season how much he impacts winning. 

His Blazers were up against it in the first round against the eventual Western Conference champion San Antonio Spurs, but the veteran Holiday still registered better than 16 points and seven assists per game. 

On a team as talent-loaded as Toronto, especially if Leonard returns to the franchise, Holiday’s impact could make the conference finals the Raptors’ floor next season. 

Now whether Portland would trade Holiday is a different story. NBA insider Jake Fischer recently reported that the Blazers hold no interest in moving Holiday at this time.

“Jrue Holiday is not going anywhere,” Fischer, speaking on the Bleacher Report NBA insider live stream notebook on Tuesday, said flatly. “… For some reason, people online love to make graphics about Jrue Holiday finding a buyout agreement with Portland; they put him in a Sixers uniform, they talk about him going to Miami.” 

Added Fischer: “The Blazers want Jrue Holiday. It doesn’t matter that Damian Lillard is coming back from a torn Achilles, it doesn’t matter that they traded for Ja Morant; Portland has no intent of trading Jrue Holiday or signing him to a buyout agreement.” 

But the Blazers have a glut of guards, and playing four of them major minutes won’t be an easy task for new head coach Micah Nori. 

Portland could use help up front alongside the rising Donovan Clingan. Reid, an offensive-oriented player, could be a strong option for the rising Blazers.

As for Toronto, Holiday has a proven track record of helping teams win a championship. He did it in Milwaukee (in his first season with the team!). He did it again with Boston three years later.

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Raptors Proposed to Trade Immanuel Quickley for 2x NBA Champion Star PG

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