Toronto Raptors’ Interest in Jrue Holiday Hints at Bigger Offseason Plans

The Toronto Raptors reportedly showed interest in Jrue Holiday before his trade to Portland, signaling a possible shift in spending and win-now roster strategy

Jan 15, 2024; Toronto, Ontario, CAN; Boston Celtics guard Jrue Holiday (4) drives around Toronto Raptors forward Scottie Barnes (4) during the first half at Scotiabank Arena. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

The Toronto Raptors were reportedly among several teams that expressed interest in Jrue Holiday before the veteran guard was traded back to the Portland Trail Blazers on Monday night, according to Jared Weiss of The Athletic.

Sacramento, Dallas, and Toronto were all linked to Holiday ahead of the deal, which sends Anfernee Simons and two second-round picks to the Boston Celtics. The move reunites Holiday with the Blazers, who originally acquired him in the 2023 Damian Lillard trade before flipping him to Boston shortly afterward.

For the Raptors, the reported interest in Holiday offers insight into the team’s shifting priorities. After acquiring Brandon Ingram at the trade deadline and stating their intent to return to playoff contention, Toronto’s involvement suggests a growing willingness to pursue veteran upgrades.

What stands out about the report is what it implies about the Raptors’ financial posture. Holiday is set to earn $32.4 million this season, meaning Toronto would have had to send out significant salary to match. The most likely trade construction would have involved RJ Barrett, who is owed $27.7 million this season. Since Boston’s primary objective was to shed salary, the only way a deal would have worked is if the Raptors were willing to take back more money than they gave up. That approach would have pushed Toronto deeper into the luxury tax.

This is notable because it suggests that Raptors ownership may be open to increased spending. It also signals that the front office is willing to prioritize roster improvement over short-term financial flexibility. While Toronto ultimately did not land Holiday, registering interest in a high-salary veteran points to a growing appetite to compete.

Toronto has been widely connected to multiple veteran players this offseason. While the trade did not materialize, the Raptors’ involvement hints at a broader openness to acquiring playoff-tested veterans, even if it comes at a financial cost.

Holiday may no longer be available, but the Raptors’ activity suggests they will continue to monitor opportunities to upgrade the roster.