Figure out if the team can move forward with Rudy Gay or DeMar DeRozan
There's no reason to move forward with a duo of wings that make nearly $30 million next season (eating into over 50% of the teams salary cap) when neither player can consistently stick a perimeter shot or is willing to get at it on the defensive end.
In fact, it's possible that neither player will be in training camp
if Ujiri can unload Gay's albatross of a contract.
You can easily argue that Gay is one of the five best players to ever suit up for Toronto so having him stick around for the next two seasons wouldn't be horrible.
DeRozan has a lot of flaws, but he's still valued highly around the NBA. With him starting a new four-year contract next season it's more likely that DeRozan gets dealt if either player is moved.