What Masai Ujiri’s Trade History Tells Us About the Toronto Raptors’ Offseason Plans

Rumors are swirling around the Toronto Raptors.

From whispers about Giannis Antetokounmpo to speculation that Toronto is preparing for a major move, the Raptors have once again found themselves in the middle of the offseason rumor mill. Whether something materializes or not, it is clear the front office is exploring big opportunities.

What that might look like depends on Masai Ujiri.

Toronto’s president has a long history of making bold decisions. He has traded for stars, reset the roster, and stayed patient when the right deal never came. Over more than a decade in charge, Ujiri has built a clear track record that offers insight into how the Raptors operate and what might come next.

If Toronto makes a move this summer, history suggests it will follow a familiar pattern. There are three themes in particular that help explain what that could look like.

Never More Than One First-Round Pick

In more than 14 years as an NBA executive, Ujiri has never traded away more than one first-round pick in a single deal.

That has held true even in his most aggressive moves. The 2018 trade for Leonard included just one first-rounder. The 2023 deadline deal for Jakob Poeltl required only a single protected first. Even during his time in Denver, Ujiri never packaged multiple firsts to complete a trade.

We also know he has been willing to. During trade discussions for Damian Lillard in 2023, reports indicated the Raptors were prepared to part with multiple first-round picks to make a deal with Portland. Ultimately, it never came together.

The willingness may be there, but the line has not been crossed. In a league where teams often send out three, four, or even five first-round picks to land a star, Ujiri has consistently chosen a more restrained path. He is aggressive in pursuing talent but stays disciplined when it comes to long-term assets.

A Pre-Agency Specialist

Ujiri has shown a clear pattern of trading for players on expiring contracts, often acquiring talent at a discount and betting on the ability to retain them.

The Raptors traded for Serge Ibaka in 2017 with free agency around the corner and re-signed him that summer. In 2018, they acquired Leonard with one year left on his deal and won a championship. In 2021, Ujiri flipped Norman Powell for Gary Trent Jr., who was also on an expiring contract.

This strategy has continued in recent years. Ujiri traded for Thad Young in 2022, Poeltl in 2023, and Immanuel Quickley in 2024, all in the final year of their deals. Most recently, the Raptors acquired Brandon Ingram in the final year of his contract and signed him to an extension.

Toronto has not had the flexibility to be a major player in free agency. Instead, Ujiri tends to get his offseason work done early, making his most important free agent signings before free agency begins.

That approach may come into play again this year. Trae Young, Zach LaVine, Jaren Jackson Jr., Coby White, Daniel Gafford, and Mikal Bridges are all heading into free agency next summer. If any become available, the Raptors’ trade history suggests they will be watching closely.

No First-Round Trades on Draft Night

Ujiri has never traded up, into, or out of the first round on draft night. Not in Toronto. Not in Denver.

Every first-round pick the Raptors have held on draft night has either been used or previously moved in a separate deal. The team has never traded up, down, or back into the first round during the event itself.

We know they have looked into it. In 2013, Toronto famously tried to trade into the first round to select Giannis Antetokounmpo. In 2018, they reportedly explored a move up the board to take Shai Gilgeous-Alexander, though they did not hold a pick that year. Neither deal materialized.

While draft-night trades are common across the league, Ujiri has consistently preferred to trust internal evaluations and stick with the pick if he has it. It is one of the few areas where he has shown almost complete restraint.

Further Reading