Here a question for you: If the Raptors hadn't signed DeMar DeRozan to an extension last October, but the rest of the season played out EXACTLY as it has, would the club re-sign him this summer?
DeRozan hasn't had a bad year, by his standards he's had a perfectly normal year, so one could safely assume that the club's opinion of him wouldn't have changed over the last five months. However, since the club has brought in Rudy Gay it's been clear that the two aren't ideally suited as a wing tandem, and if the club was going to dive into their future with just one of them, you'd have to assume it would be Gay.
The big problem stems from their similarity as players, the same red flag that many pointed to as the Gay acquisition neared completion back in January. Neither one is great at creating offense for other people, both settle for a lot of long jumpers and both tend to need offensive sets to revolve around them to be at their best. One of the most difficult balancing acts the team has had to strike since bringing Gay aboard has been figuring out how to satisfy the needs of two such similar players, and the team's offense struggles more often than not as a result of that effort.
What it really comes down to is rhythm. Guys like DeRozan and Gay are rhythm players; get them going and they can look unstoppable, but go away from them for too long and that rhythm breaks down. Since Gay's arrival the two share more per-game minutes in tandem then any other two-man combo on the team, meaning that they are frequently forced to try and balance the offense between the two of them. That makes sense on the one hand because it splits up the defensive attention one would have to battle on their own, but it's also an odd choice considering there are stretches when both are on the bench together rather than having one anchor the offense with the second unit.
That first factor is further neutered by the fact that the DeRozan and Gay combination rank 31st on the team in offensive rating, effective field goal percentage and true shooting percentage (minimum five games played together) according to nba.com's stats tool. While the theory is that both can operate with more freedom because of the defensive attention the other one commands, that hasn't actually translated into a more efficient offense for the team thus far.
Plus, it should be noted that both players have shot worse since the trade went down and the team's offensive rating on the whole has fallen off since Gay arrived.
A more damning indictment of this wing combination, though, is this: not only have DeRozan and Gay not shot 50% each in the same game, more often than not when one does shoot 50% the other one shoots for a terrible percentage. When DeRozan has shot 50% or greater in a game, Gay has averaged 32.5% shooting. When Gay has shot 50% or greater in a game, DeRozan has averaged 35.9% shooting. Basically, when one excels and becomes the focus of the offense, the other one suffers dramatically. Not only that, the Raptors are one game below .500 in games where one of DeRozan or Gay shoots 50% or better, which isn't surprising given that one's success tends to be offset by the other's failures.
So is all of this meant to suggest that the Raptors would have been better off letting DeRozan walk this summer? No, but perhaps using him in a sign-and-trade to help ease roster duplication would have helped balance out the team's attack. It's worth noting that while the DeRozan-Gay tandem ranks 31st on the roster in offensive rating, Gay and Terrence Ross rank fourth (101.5 points scored per 100 possessions versus 105.8 points scored per 100 possessions).
The reality of the situation, though, is that DeRozan was inked to a four-year, $38-million deal back in October, and it is unlikely that team will even explore trading him as long as Bryan Colangelo is at the helm. Despite the uninspiring fit, the Raptors seem enamored with the prospect of going forward with this pair manning the starting wing spots (perhaps it's also worth mentioning that the DeRozan, Gay and Kyle Lowry troika ranks 58th on the team in terms of offensive rating from a three-man combination, though defensively they measure out very nicely).
This is why so many pundits are only lukewarm about the prospects of this team going forward. The organization can nip-and-tuck around the edges of the roster this summer, but that can only help so much when the marquee pieces fit together to uncomfortably.
The best teams in the league design their rosters to maximize the strengths of their best players (it's why Gay was jettisoned from Memphis in the first place), but the Raptors have invested heaviest into players that seem to limit the effectiveness of one another. Maybe they have bolder plans up their sleeves than most expect, but if this is going to be the shape of the club in 2013-14 then one had better hope that Jonas Valanciunas takes a quantum leap before next season.