B/R’s Raptors-Spurs trade is a very risky move for Masai Ujiri

Masai Ujiri and the Toronto Raptors have made a habit of trading with the San Antonio Spurs in recent years, as Thad Young and Jakob Poeltl were both taken away from the last few years of Gregg Popovich’s tenure and placed on a Raptors team that is (allegedly) trying to compete for a championship despite players like Malachi Flynn taking up bench time.

Flynn is one of a few Raptors players who could be kicked to the curb at the end of the season, as he has either stagnated or regressed in many key developmental areas since joining Toronto. A fresh start is needed for both parties at this stage.

The Spurs will be interested in any deal if enough pick compensation is attached, which could get them back on the phone with Ujiri once again. One trade that could interest both parties involves sending Flynn down to Texas.

Bleacher Report’s Zach Buckley proposed a trade in which Flynn and some pick compensation are sent to San Antonio in exchange for Doug McDermott. This does help the Raptors fill a big need, but the price tag associated with it could be too steep for Toronto.

This Raptors-Spurs trade sends Malachi Flynn to San Antonio.

In a vacuum, swapping Flynn for McDermott might actually appeal to Toronto. The Raptors would get a player that can give them more expert perimeter marksmanship on an affordable contract, and the Spurs will get a shot to revitalize Flynn’s once-promising career in San Antonio.

Despite what some recent trades would have you believe, second-round picks are not valueless pieces that can be traded so flippantly, especially for a team like the Raptors that has issues bringing in quality free agents. Toronto must draft and develop well, and giving five picks to San Antonio in 15 months would be bad business.

Acquiring McDermott, who has averaged 11.8 points per game while making 41% of his 3-pointers in the last few seasons, isn’t that dissimilar from the Poeltl acquisition. He is a fine player who will undoubtedly help fix a fatal flaw on this team, but he has one issue (in McDermott’s case, defense) that could sink him.

The Raptors need to be very careful about trading picks, as they could end up in debt to San Antonio for a team that isn’t going to win a title anytime soon. If they can acquire McDermott through less taxing means, that possibility should be pursued with great fervor.