DeMar DeRozan’s potential contract extension: The good, the bad and the ugly

DeRozan’s case (from a contractual standpoint)

The 2019-20 season will mark year four of DeRozan’s five-year, $139 million deal — a deal that made him the highest-paid player in the NBA at the time. This summer, the Spurs would have the chance to extend their four-time All-Star to a deal, though neither side has come to a conclusion there yet.

Not that it matters to the Spurs and their historical framework, but DeRozan will be in his early 30s when it becomes time to work a new contract out. With that, the Spurs will have two questions to ask themselves:

1. Is a championship realistic with DeRozan as the alpha (or co-alpha dog), and
2. Do they trust that DeRozan won’t decline his player option after the 2019-20 season and become an unrestricted free agent?

The latter of the two serves as the focal point for potential panic. Should the Spurs run that risk, not only will they have undersold on what they could’ve gotten for what some call the best player in basketball at the time (though his value had declined at the time), but they could also lose out on the major return for that trade.

Because the player option doesn’t come into effect until after the 2019-20 season, the Spurs could wait, but all of that hinges on whether they want to get a head start on their new regime. They’ve stockpiled guards, and all three of their draft selections were wing threats.

With free agency set to begin on June 30, the Spurs have been linked to numerous players of similar position to DeRozan, such as Bojan Bogdanovic, Trevor Ariza and Harrison Barnes (unlikely, unless Barnes elects to take the mid-level exception). For Bogdanovic in particular, the only way this happens is if the Spurs move DeRozan’s contract.

The pros and cons are aplenty for each side, though the biggest for the Spurs could be the discount they get by re-signing or extending DeRozan. While the max contract DeRozan could receive is closer to $175 million, the Spurs could get a $25 million discount, should they offer him the max of $149.1 million over four years this summer.

By this point, history doesn’t prove DeRozan to be the type of focal point of a title team. However, he remains a solid culture fit. All told, he’s also a pivotal part of a team that came a few blown leads away from beating the No. 2-ranked team in the Western Conference in Denver. If the Spurs trust that they can break through with DeRozan and LaMarcus Aldridge as the catalysts, the question of whether they should take the discount becomes much easier.