DeMar DeRozan and Kawhi Leonard were dealt for each other in a franchise-altering move for the Raptors.
  • DeMar DeRozan and Kawhi Leonard were dealt for each other in a franchise-altering move for the Raptors.
  • Norman Powell and OG Anunoby were involved in one of the best trades in Raptors franchise history.

Masai Ujiri’s five best and five worst moves with the Raptors

We break down the moves that worked out best, and some that didn’t, with Ujiri at the helm of the Raptors for a decade.

A look at some of the best moves made by Masai Ujiri in his decade at the helm of the Raptors and five that didn’t work so well.

FIVE HITS

July 18, 2018 — Trades DeMar DeRozan, Jakob Poeltl and a draft pick (Keldon Johnson) to San Antonio for Kawhi Leonard and Danny Green.

It’s peak Ujiri. Unafraid of any backlash from trading a franchise icon he took a bold gamble on Leonard, who had been hurt and, with one year left on his contract, was not a long-term investment.

It won the Raptors a championship and there haven’t been lot of them around these parts in the last half-century.

June 25, 2015 — Trades Greivis Vásquez to Milwaukee for the draft rights to Norm Powell and a future pick that turned out to be O.G. Anunoby.

This was Grand Theft Basketball, pure and simple. While Vásquez was an OK player, he’d reached his ceiling and finding one promising young player for him was a good return. Getting two put the deal way over the top.

Dec. 8, 2013 — Trades Rudy Gay, Quincy Acy and Aaron Gray to Sacramento for Chuck Hayes, Patrick Patterson, John Salmons and Greivis Vásquez.

Ujiri will admit he had no idea if the deal would benefit the Raptors. And if it hadn’t he would have been fine with it starting a big rebuilding process.

What it did was signal the real start of the Kyle Lowry/DeMar DeRozan partnership and put the Raptors on a path to an NBA championship.

July 10, 2013 — Trades Andrea Bargnani to the New York Knicks for Steve Novak, Marcus Camby, Quentin Richardson and draft picks that became Xavier Thomas, Jakob Poeltl and Jonah Bolden.

It was Ujiri’s first move after returning to Toronto from Denver and moved the Raptors on from the former No. 1. Camby and Richardson never came, Novak had no impact, Thomas and Bolden were nothing, but Poeltl helped. The big message was that Ujiri would be proactive in changing the roster.

Summer of 2016 — Drafts Pascal Siakam 27th, Jakob Poeltl ninth and signs undrafted guard Fred VanVleet.

Siakam and VanVleet were key pieces in Toronto’s 2019 NBA championship and remain mainstays. Poeltl was part of the Kawhi Leonard trade, and is seen as a key piece for the future now that he’s back. Hard to think of a better Raptors off-season.


FIVE MISSES

March 25, 2021 — Trades Norman Powell to Portland for Gary Trent Jr. and Rodney Hood.

It was a major move in the Tampa Tank year and the Raptors were worried about what they’d have to pay Powell in the summer of 2021. But today, Powell will likely end up earning less than free-agent-to-be Trent. He’s just as good a player, if not better, and more suited to a bench role the Raptors need filled.

June 26, 2014 — Drafts Bruno Caboclo in the first round.

There was no harm in taking an intriguing teenage talent such as Caboclo with the No. 20 pick. The miss came when the Raptors failed to find a way to develop the six-foot-nine forward into an NBA player.

A year spent in a top European league would have helped. Not having a say in any time he spent in with the D League’s Fort Wayne Mad Ants held him back too much.

Summer of 2020 — Signs Aron Baynes and Alex Len as free agents.

The year the Raptors spent in Tampa purgatory ended all right with the drafting of Scottie Barnes, but trying to coax legitimate NBA play out of two journeymen centres was a stretch.

July 1, 2015 — Agrees to sign DeMarre Carroll as a free agent.

Signing Carroll to a four-year, $60-million contract certainly was a splash because he was coming off two excellent seasons in Atlanta. It ended up more of a belly flop than a swan dive — Carroll wasn’t a good fit on the court or in the locker room — and Ujiri had to attach two future picks to move his contract to Brooklyn. Those picks turned into nothing (Rodions Kurucs and Dzanan Musa) but the original $60 million could have been better spent.

Nov. 18, 2020 — Drafts Malachi Flynn over Desmond Bane.

The draft is a crapshoot most of the time, and that’s doubly true when you’re talking about the 29th selection.

And while Flynn may end up being an NBA talent — his development has been stalled by infrequent use — Bane, taken with the next pick, has become a key piece already with the Memphis Grizzlies.

Doug Smith is a sports reporter based in Toronto. Follow him on Twitter: @smithraps
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