No. 2: Gary Trent Jr.
Last offseason it was commonly expected that Gary Trent Jr. would decline his player option and depart Toronto in free agency for a longer, more lucrative contract. Instead, perhaps expecting a frigid market, he picked up the player option and played another season with the Raptors.
The former Duke shooting guard may regret that decision, but it's not entirely clear what his market will be. On the one hand, his role decreased and he played both fewer minutes and took fewer shots. On the other hand, he shot 39.7 percent from 3-point range and most teams would likely sign him to play a specific 3-and-D role.
It's possible that Trent returns to the Raptors, especially if he finds a dry market in free agency, but after they drafted Gradey Dick and traded for RJ Barrett and Ochai Agbaji the wing rotation is filling up quickly. Spending significant money on Trent doesn't seem like it's in the cards.
Trent will more likely sign with a mid-tier team for something around the full mid-level exception and continue his career. He could also look to sign a short-term deal again and try to improve his value, but that didn't work this past season. Either way, the odds of Trent returning to the Raptors seems fairly low.