Grade the Trade: Raptors deal big man for Cavaliers guard in latest proposal

Should the Raptors make this deal?

One of the weaknesses of the Toronto Raptors last season, throughout every iteration of the team, was on-ball defense on the perimeter, and especially at the point of attack. From Dennis Schroder to Malachi Flynn to Immanuel Quickley to Javon Freeman-Liberty, opposing guards were not being locked up and were getting into the paint with an advantage.

Isaac Okoro addresses that weakness as one of the league's best point-of-attack defenders, someone who can attach himself to opposing ball-handlers and follow them around the court, fighting over screens and slithering into position to steal the ball or contest shots. He is likewise relentless in ball denial, forcing opposing teams to change their play call because their point guard can't get free to run the play.

With that being said, the Raptors already addressed that need this summer. Davion Mitchell is right there with Okoro in that top tier of on-ball defenders, while Jamal Shead was one of the best guard defenders in the draft, and both offer backup point guard skills that Okoro has never developed. In fact, one of the reasons the Cavaliers are not prioritizing Okoro's return is that he has essentially settled in as a cutter and below-average catch-and-shoot player, never adding the on-ball shot creation he showed flashes of in college at Auburn.

Toronto also has a guard room just as crowded as the Cavaliers' with as many as seven players whose most natural position is shooting guard, alongside another three point guards. Turning a big man into a shooting guard only exacerbates the problem. On the other hand, most of those guards are used to only playing guard, while Okoro has plenty of experience at forward and could slide in as the backup to RJ Barrett at the 3.

$32.2 million over three years is excellent value for Okoro, whose shaky jumpshot is improving and whose defense is consistently underrated because he is so often called on to play out of position. When he has been deployed at the 2 next to an on-ball star like Donovan Mitchell or Darius Garland, with real forwards on the court, those lineups have sung. The Raptors could try to capture that, and the opportunity cost is not extravagant.

If Okoro was 6'7" or shot a few percentage points better on 3-pointers this would be a different conversation. As it is, moving off of Boucher and getting a player who can continue to develop makes a lot of sense, even if the fit is a difficult one. This is likely a deal worth making, but it would also make sense to pass and look for a different option.

Grade: B