Why DeMar DeRozan Won’t Get the Max Contract He Wants

Demar DeRozan has had a strange career. He’s one of the best shooting guards of his generation, averaging 20 points a game for his career. He’s on track to hit that mark again this year. He’s one of the foundational players that helped the Toronto Raptors work their way out of perennial mediocrity to become a franchise that regularly made it to the latter stages of the Eastern Conference playoffs. His public vulnerability about his issues with anxiety has also won him many admirers. And yet, as he approaches unrestricted free agency, the four-time All-Star’s future in the NBA is as unclear as it’s ever been. 

DeRozan’s style comes from a bygone era

DeMar DeRozan is a standout NBA veteran, but he shouldn't expect a big contract when he hits free agency in 2020.
DeMar DeRozan (middle) puts up a contested shot. | Jim McIsaac/Getty Images

DeMar DeRozan has always been a player out of another era. Now, the effects of that iconoclasm are increasingly profound on his standing in the league. Most GMs believe in the analytics-based idea that mid-range shots are rarely worth taking. It’s smarter to either step back a couple of feet and take a more valuable 3-point shot, or get closer to the rim where you can get a layup or draw a foul, especially if you’re a wing player. DeRozan has shown that he can get to the line, but his sphere of influence is not a modern one.

He’s never been a consistent or willing 3-point shooter. The reasons behind that reticence are understandable. DeRozan has shot a paltry 28% from deep during his career, and only once has he averaged more than three 3-point attempts a game. DeRozan made his bones in the league by becoming an excellent mid-range scorer. But that skill isn’t worth as much as it used to be a few years ago. As the league becomes more and more obsessed with long-range shooting — and less enamored with inefficient long twos as a result — his stylistic quirk in his game has become an increasingly glaring deficiency. 

The rest of DeRozan’s game isn’t advanced enough to make up for the lack of range on his jumper. He’s not good enough as a passer to be anything more than a secondary playmaker. Despite an impressive frame, he leaves a lot to be desired as a defender. 

DeRozan tends to struggle in the postseason

DeMar DeRozan’s playoff woes could also scare off potential suitors. The Raptors teams he led became such a joke that they became known in some internet circles as LeBronto in recognition of the many times that LeBron James swiped them aside with ease. Eventually, Toronto GM Masai Ujiri decided things had to change, and DeRozan was a centerpiece in the trade with the San Antonio Spurs for Kawhi Leonard. 

DeRozan’s connection to the Raptor fanbase is so strong that the trade was briefly controversial, but Toronto’s Kawhi Leonard-fueled run to the NBA title erased any sadness the fans felt. No one ever expected DeRozan to turn into a generational superstar. Still, it’s not a great look when your former team takes such a dramatic leap in results immediately after trading you. 

DeRozan is still putting up decent numbers with the Spurs. He and LaMarcus Aldridge helped get them back into the playoffs last year, a real achievement considering the depth in the Western Conference. This year’s 12-17 record suggests that this could be the first season where San Antonio misses the playoffs in over two decades as the franchise ponders giving the reins to young and budding stars

A max contract isn’t likely for DeMar DeRozan

Add up all those factors up, and it doesn’t seem shocking that a player with a pedigree like DeRozan’s might not get a big, long-term contract. It’s difficult to envision a team with significant cap room looking at DeRozan’s skill set and deciding that he would be worth more than $30 million per year. One NBA executive believes DeRozan is more of a third option on a team, and those players rarely receive big-money deals.

His best attributes are not valued by the modern NBA. He’s also now in his 30s, so his most productive years are likely behind him. Demar DeRozan is still one of the best potential free agents next summer. That sounds impressive until you actually look at the list of available players next summer. It’s hard to imagine a big payday is awaiting him when he becomes a free agent.