No. 2: Gary Trent Jr.
The only longtime Raptor on this list, Gary Trent Jr. did not have to be on the Toronto roster this past season. A year ago he picked up his $17.5 million player option after it became apparent that more money would not be waiting for him on the open market. His plan was to have a career year in his contract season and set himself up for a long-term deal this summer.
That move was not a colossal failure, as Trent did have an excellent year shooting the 3-pointer. On similar volume per-minute to his career averages he shot 39.3 percent, his best percentage since joining the Raptors in 2021. As a 3-and-D wing it's important to point to a track record of doing the '3' part well.
Unfortunately for Trent, that's about all that he did well this past season. Trent was less active inside of the arc, taking just 5.5 shots per game inside of the arc and shooting just 46.4 percent on them. His free throws were therefore down significantly at just 1.4 attempts per game, and most of those were fouls on 3-point shots.
Defensively, Trent was a sieve, hardly the lockdown perimeter defender the Raptors needed him to be. He also posted steal and block rates well down from the past two seasons in Toronto and below his career norms.
In a season where the Raptors desperately needed someone to step up and take on more of the scoring load, Trent's usage rate went down. He hunted high-percentage 3-point shots but otherwise didn't do much to contribute on a team that could have used him. Add in the stench of a 25-win season, and it's extremely likely that Trent's market in free agency will be less than he hoped, and less than projections heading into this season.
An interesting question for Trent and Toronto therefore becomes whether he hits the open market for whatever he can find, or whether he accepts a low number from the Raptors to try again.