Ranking the top 5 potential trade partners for Blazers’ Anfernee Simons

5. Toronto Raptors

The Toronto Raptors finished last season with a 25-57 record. That does not fit the criteria for giving Simons the chance to win. But they are at least retooling and trying to remain competitive, as opposed to the Blazers, who are rebuilding and doing everything they can to land a top draft pick next year.

Simons is an ideal fit with the Raptors' timeline. Toronto's core players are Scottie Barnes (23 years old) and former New York Knicks Immanuel Quickley (25) and RJ Barrett (24). The 25-year-old Simons would be an excellent addition to the Raptors' strategy of attempting to win in the next few years as these players enter their primes together.

The main concern would be defensively, as Quickley and Simons would be an undersized backcourt; this issue is the main thing that keeps Toronto at No. 5 in the ranking. But both are combo guards and would give the Raptors lineup flexibility to keep one guard on the court at all times, surrounding star Barnes with elite shooting and secondary playmaking to optimize his strengths and negate his weaknesses.

For the Blazers, Toronto has Bruce Brown, who they could either keep or flip for additional assets. 20-year-old Kansas guard Gradey Dick would be another intriguing piece as a 6-foot-6 shooter to bring off the bench. However, in any deal involving Simons, the most likely focal point of the trade for Portland will be draft compensation. He should require at least two first-round picks to be moved. The Raptors have two 2026 first-round picks, one of which is the top four protected by the Pacers, which would be a great starting point in potential trade discussions.