Oklahoma City Thunder: Lu Dort - 2 years, $34 million
Over the last few years, there may not be a team in the NBA that has managed to handle their contract situations better than the Oklahoma City Thunder. They don't have any bad contracts on their books at the moment, but one player who is up for an extension soon is Lu Dort. Because of how deep the Thunder are at the moment, I'm not sure he's a player Oklahoma City should rush to extend.
Because of that, it could create somewhat of a difficult situation for the team. In an attempt to get ahead of either a big overpay or some real financial issues, the Thunder should probably try to trade Dort this offseason. It may not be a popular move, especially considering what his development has meant for the team, but it's probably the right one if the Thunder wants to keep at least some financial flexibility moving forward.
Orlando Magic: Kentavious Caldwell-Pope - 2 years, $44 million
Would it be that controversial to say the Orlando Magic made a mistake in signing Kentavious Caldwell-Pope last offseason? With how inconsistent he's been so far this season, I don't think that's unfair. Even though KCP played much better during the last month of the year, he certainly had his struggles. At the very least, he hasn't been the consistent, reliable veteran presence that Orlando believed he could be for them when they signed him.
I'm sure a strong performance in the NBA Playoffs could certainly change the narrative surrounding KCP this season, but if that doesn't happen, I don't believe it would be that outlandish to suggest that the Magic should probably explore the possibility of trading him during the offseason. Opening up more than $20 million per season could go a long way in giving the Magic more flexibility to operate elsewhere.