Small Forward: OG Anunoby
While Anunoby has been the subject of a great many trade rumors during this part of the season, the best path to success for the Raptors is still centered around keeping him in town and signing him to a nine-figure extension that makes him one of the highest-paid wings his age in the league.
His defensive skills, 3-point shooting, and complementary fit alongside Scottie Barnes are difficult to get in three separate players, let alone one package. OG could fetch quite a haul, but trading Siakam for a bigger collection of assets, and rolling with Anunoby alongside Barnes might be the more prudent move.
The Toronto Raptors should not trade OG Anunoby.
Shooting Guard: Gary Trent Jr.
While Trent got off to a borderline unwatchable start this season, he looks like his old self once again. After putting up a goose egg eight games ago against the Charlotte Hornets, Trent has shot 44% from the field and slightly over 40% from 3-point range on 7.1 attempts from deep per contest.
Trent may not have made himself a ton of money ahead of his impending free agency, but the last few weeks have reaffirmed the notion that he is a tremendous shooter who can be a weapon when he's hot. Toronto needs more players like him, but one in the starting lineup will have to suffice for now.