In 245 days, DeMar DeRozan is going to be a free agent and we have no idea what's going to happen with him and the Raptors when that time arrives.
When Toronto drafted DeRozan ninth overall back in 2009 he was looked upon as a transformational, potentially cornerstone-level player. Names like Andre Iguodala and Vince Carter were thrown around as comparisons, and the club inserted him into the starting lineup on Day One as a way of kick-starting his development as an NBA player.
Since that time, though, DeRozan hasn't progressed exactly as expected. He's developed into a scorer capable of dropping 20 ppg, sure, but as ESPN's stat guru John Hollinger noted last month, "few players score an emptier 20 than this guy."
The criticisms lobbed at DeRozan are that while he can put points up on the board he does so with increasing inefficiency, as his shot attempts per game have risen each year while his true shooting percentage has fallen off right alongside. To compound matters, DeRozan doesn't offer much help as a passer, rebounder or defender, which tremendously lessens his impact in games where he's not scoring. He offered a PER of just 12.68 last season, which is not only below the league average but was only good for 38th amongst NBA shooting guards, behind guys like Shannon Brown, Nick Young and Willie Green.
All of this has led the Raptors organization to refrain from offering DeRozan a contract extension this fall, in spite of the fact that they routinely describe him as a core piece to their future. Given his career to date, there is just no way that the club and the player were going to agree on his value and so DeRozan will test the open market in eight months' time.
That puts the Raptors in a precarious spot with DeRozan this season.
Based on his career to date, DeRozan is not an NBA-caliber starter at shooting guard. He doesn't do enough, he's not efficient enough and, ultimately, he hasn't proven reliable enough to justify that role. There is a reason that the Raptors weren't particularly eager to lock him up this fall, and that suggests that the organization has a fairly sober view of DeRozan after his first three seasons with the club, despite what they may say about him publicly.
Still, DeRozan represents an asset for the Raptors, and one that they have to be very careful with if they want to maximize his value.
In a best-case scenario, DeRozan has a breakout season and he and the club work out a frictionless extension next summer. Considering the fact that he's just 23 years old and has already logged 6,721 NBA minutes, he's certainly in a position to take a big step forward this season. In preseason play he's looked more comfortable with his handle, which should open up some options for him on offence, and he looks more active on defence, too, which should help him stay on the floor (though his rotations still leave a lot to be desired). He's also managed to shoot .461 from the field, which is encouraging after dropping to .422 last season.
There is a flip side to that coin, though.
The Raptors are demanding that DeRozan get himself to the free throw line A TON this season. They've conceded that he can't hit threes, but he has to make up for it by living at the stripe. To that end, DeRozan started off the preseason like gangbusters when it came to getting to the free throw line, but in the end only averaged 5.7 free throw attempts per game. Now, that works out to over 7.6 attempts when his minutes are adjusted to the 35-minute per game level he averaged over the last two years, but for DeRozan even that is not enough.
After getting to the line 19 times in his first two games, he got there only 21 times in his next five, and he had zero attempts in his last preseason contest against the Grizzlies. If DeRozan is not going to hit threes then he needs to get to the line 9 to 10 times per game. Sound like a lot? It is, but if he is going to be a starting wing that doesn't hit threes, rarely rebounds and doesn't make plays for others, he's going to have to find high-efficiency production somewhere on the stat sheet. Corey Maggette, a good comp for DeRozan, went for nearly 10 FTA per 36 minutes during the most effective stretch of his career, and like DeRozan he had to because he didn't shoot threes or pass the ball (although even Maggette assisted more than DeRozan does. Chew on that nugget for a second).
What might help DeRozan tremendously to this end is if the club can get him consistently into the post against smaller backcourt opponents. The Raptors featured him there a lot against Milwaukee in preseason play and DeRozan was quite effective (of course, he also let Monta Ellis go off for 26 points, so it was kind of a wash on the night). It's all about finding a way to make DeRozan an efficient contributor on a nightly basis, because if they can't do that then the club is going to be left holding the bag when free agency rolls around.
So the big question facing the Raptors this season is what happens if DeRozan doesn't markedly improve before he hits free agency? Bryan Colangelo has never not extended a lottery pick, and he has a reputation (fair or not) for overvaluing guys that he finds in the draft, but even he has never faced a scenario like the one he faces with DeRozan.
In reality DeRozan should be a backup shooting guard, but the Raptors have spent so much time pimping him as a starter that they can't very well turn around and expect DeRozan to accept bench player money at the negotiating table. Conversely, they cannot pay him like a star or even a near-star shooting guard because he doesn't have the game to justify it. If he gets there this season, gravy and thank the stars, but if he stays at the same relative level he's been at over his whole career in Toronto then the club has painted itself into a bit of a corner.
It will be very interesting to see what happens around February's trade deadline, then, because that might wind up being Toronto's best opportunity to maximize DeRozan's value if he doesn't have a breakout campaign this year. Pair him and Jose Calderon's $10.6 million expiring contract and the Raptors have a nice nugget to dangle over the market. It's not a killer package, but it's enticing and should be able to get them pieces that at least fit the direction of the club better even if they don't meaningfully upgrade the level of talent.
Again, if DeRozan takes a step forward this season then all of this conversation is moot. The Raptors organization is behind him and want to make it work with him in their ranks, but they have to be realistic with what they have and where they want to get to as a franchise. They aren't going to be precious about players, they can't afford to be, so DeRozan has to give them a reason to pony up for him in free agency over the next 245 days or else it will be hard for the club to justify the terms that it would take to retain him. The team's hopes for him remain high, but right now those hopes center on him justifying the role the club has already gifted to him. If he manages that the club will happily reward him. If not, they are going to have to make some very hard decisions between now and July 1.