Ujiri on DeRozan’s training with Olajuwon, 4-point line, Caboclo

Golden State Warriors' Kevin Durant spoke with Eric Smith following the Golden State Warriors 117-112 victory against the Toronto Raptors Wednesday

Toronto Raptors president of basketball operations Masai Ujiri made a guest appearance on the Bill Simmons Podcast on Wednesday. Over a sprawling, hour-long conversation, Ujiri, the first and only non-American to win Executive of the Year, covered a wide range of basketball-related topics, from his rise up the front office ranks, to present and future NBA trends, the struggles in Bruno Caboclo’s development, and how DeMar DeRozan‘s footwork became the envy of the league.

Here are some quotes and takeaways from the interview:

Adam Silver’s advice kept Ujiri in an NBA front office

Ujiri and Silver, the NBA commissioner, have a friendship that dates back to his earliest days in the league, when Ujiri was volunteering his time scouting for the Orlando Magic. As Ujiri rose up the ranks with the Denver Nuggets and eventually took a job as the Raptors assistant GM working under Bryan Colangelo, he wanted a change of scenery, and prepared to take a job working with at the NBA’s office in Johannesburg, South Africa.

Silver told him not to take the job, warning that he’d be missing a big opportunity and that the posting in Johannesburg would still be there for him later in his career if he wanted it. One month later, Ujiri said, the Denver Nuggets contacted him to interview for their general manager position, which he got and where he established himself as one of the brightest minds in the league.

Hakeem Olajuwon helped hone DeRozan’s world-class footwork at his ranch in Houston

“When I think of footwork,” said Ujiri, “I think of Hakeem.” And for good reason. The Hall of Famer made a career out of exposing defenders with his next-level footwork, and in his retirement has hosted numerous players for private one-on-one workouts. Ujiri has sent many of his players to work with the legendary centre, including Jonas Valanciunas, JaVale McGee, and DeRozan.

“He has this gym in Houston, I don’t know if you know, in the middle of nowhere basically,” Ujiri said. “He has this gym, and you go on. … It’s so absurd, it’s on a ranch or something. Inside it’s just the echoes of a ball and there’s this big picture of his jersey. … He just teaches, and it’s incredible how he teaches.”

Earlier this summer on Simmons’ podcast, reigning Finals MVP Kevin Durant said DeRozan has the best footwork in the NBA, and it seems Ujiri agrees.

“In this era now, DeMar has kind of mastered it in a way that is unique. People pay attention to it.”

“[The NBA] will change again”

Ujiri and the Raptors have made a conscious effort to adapt to today’s NBA, and currently rank second in the league in three-pointers attempted at 36 per game — more than any single-game mark the team reached all of last season. But he knows this, too, will likely soon pass.

“It’s a copycat league,” Ujiri said more than a few times over the course of the interview. He mentioned how verticality — a term made popular when Roy Hibbert and the Indiana Pacers reached the Eastern conference Finals back in 2013 before small ball became the movement it is today — was a popular trend, and how quickly that changed. “It’s just a matter of time” before the league heads in another direction from what we’re seeing today, he said.

In Denver, he recalled, he’d often ask head coach George Karl: “’We have two great big men, why are we playing a shooting four, and playing smaller when we’re playing [Andrew] Bynum and [Pau] Gasol?’ George would play Al Harrington, for instance, and stretch the floor and trying those things. But we never won a championship. Phoenix played that way [too] and came close.

“We’re a trendy league, a copycat league,” he said. “We just go with the waves.”

A four-point shot would be “interesting” in the NBA

Speaking of charting what’s next in the NBA, Ujiri mentioned that the notion of a four-point shot could be interesting, and that his team is constantly trying to be ahead of the curve in terms of mapping future trends.

When I was at the Raptors practice facility late in the summer, the Raps’ assistant general manager and VP of player personnel, Dan Tolzman, told me that he and Ujiri had been discussing the possibility of the league extending the three-point line further out, particularly in the corners. If there is a radical change like that in the NBA’s future, there’s a safe chance that Ujiri & Co. had already at the very least discussed it at one point or another.

“We think [Bruno Caboclo] is close, but it’s still a process”

Always a popular — and contentious — topic in Raptorland, the drafting of Caboclo came up early in the conversation (albeit as a pseudo-setup to a discussion on Giannis Antetokounmpo and striking rich via the draft). Ujiri explained what he saw in Caboclo, what he may have done differently, and why the absence of a D-League team at the time of the draft may have set the Brazilian back:

“We saw the shooting ability, and then you see the length — a seven-foot-seven wingspan — and a kid who is passionate about the game,” Ujiri explained. “Sometimes I wonder if I should have left him longer [in Brazil], to develop him a little bit more. But sometimes [there] they don’t concentrating on weights, on him getting stronger. We’ve concentrated on that, and it’s still been a long process.

“We didn’t have a D-League team for a couple of years, so when you’re buried it was difficult for him to play anywhere. You can shoot all you want and develop all you want [but] if you’re not playing games … it’s a work in progress. It has to get to a point where you say ‘Are you doing this, or are you not?’ Do you have to move on from it? He’s close. We think he’s close, but it’s still a process.”

On management advice

Simmons, who had to oversee a staff group for the first time in his career at Grantland and again at The Ringer, asked Ujiri what advice he would give for those in a similar position, and his answer was fairly profound:

“Be more passionate than ambitious,” Ujiri said.

He quickly added: “And hire women,” before explaining the importance of bringing women into management roles. If you didn’t like Ujiri before…

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