SportsBasketballRaptors

Toronto Raptors' trade interest in two-time NBA champion falls through

Adam Laskaris
Adam Laskaris
|
Jun 24 2025, 4:21 pm
Toronto Raptors' trade interest in two-time NBA champion falls through
John E. Sokolowski/USA TODAY Sports

Stop me if you’ve heard this one before: the Toronto Raptors were interested in a trade piece that they didn’t end up acquiring.

On Monday night, the Boston Celtics and Portland Trail Blazers made a major trade deal, sending two-time All-Star and two-time NBA champion Jrue Holiday from Boston to Portland in exchange for Anfernee Simons and two second-round draft picks.

While it isn’t quite a league-shattering deal, the 35-year-old Holiday still carries a pretty large resume along with him, which also includes gold medals from the last two Olympic Games.

The move also signifies a franchise in Portland that’s looking to return to the playoffs after a 36-win season, while the Celtics are seeking to get younger in the wake of star Jayson Tatum’s Achilles tear, which likely derails their championship hopes for next season.

And it appears that the Raptors may have had a similar thought process to Portland, as per The Athletic’s Jared Weiss.

“Sacramento, Toronto and Dallas were all interested in Jrue Holiday, but he lands back with the Blazers team that flipped him to the Celtics two years ago,” Weiss wrote. “Rumblings started moving earlier this evening that the Blazers were serious about bringing in Holiday to fortify their defensive culture as they make a playoff push next season.”

What would a Raptors trade offer for Holiday look like?

On Monday, Raptors assistant general manager Dan Tolzman admitted that they’ve received offers for the No. 9 overall pick in this year’s draft, although it’s not clear if that would’ve been part of the package for any deal.

Simons is a 26-year-old entering a season where he’ll earn US$27.6 million in the final year of his deal, following a year in which he averaged 19.3 points, 2.7 rebounds, and 4.8 assists per game.

Looking at Toronto’s roster, the closest match to a player like Simons is probably 24-year-old RJ Barrett, who put up 21.1 points per game, 6.3 rebounds, and 5.4 assists last season, slightly higher numbers in all three categories. He is signed for each of the next two seasons, making a cap hit of US$27.7 million this coming year, though he might be less of a focal point of the team’s offence with the addition of Brandon Ingram.

With the NBA Draft starting on Wednesday, we are sure this won’t be the last trade rumour we hear this week involving the Raptors.

ADVERTISEMENT