Extra Points: Toronto Raptors President’s Bold Moves Paid Off — and Business Owners Should Take Note

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Christopher Schobert
Director of Communications
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May 31, 2019
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Pointman’s Extra Points series highlights lessons in leadership inspired by today’s headlines.

TAKEAWAY: Sometimes calculated moves pay off in a big way — just ask Toronto Raptors president Masai Ujiri.


OK, show of hands. Who predicted the Toronto Raptors would earn a trip to the NBA Finals this year?

If your hand is raised, congrats — you had more faith than most of the basketball world. After all, following 2018’s playoff loss (AGAIN) to Cleveland, Raptors president Masai Ujiri embarked on a series of moves best described as very, very risky.

The former player, scout and GM began by firing head coach Dwayne Casey — fresh off a franchise-best 59-win season — and promoting assistant Nick Nurse. (Ironically, Casey was named Coach of the Year after his firing.) Two months later, Ujiri made an even more shocking move. He traded four time All-Star DeMar DeRozan, the face of the franchise, to the Spurs for oft-injured forward Kawhi Leonard.

It’s worth noting that Leonard, a former NBA Finals MVP, was set to be an unrestricted free agent after the 2018-19 season.

The response to the moves was, well, mixed. Consider a few of the headlines from last July: “Making sense of Masai Ujiri’s cold-blooded summer” was one. Or, my favorite, “Red flag Kawhi Leonard trade will be career-defining for Masai Ujiri.”

“At some point you have to do something different,” Ujiri said following the Leonard trade.

For Ujiri, doing something different involved taking a series of calculated risks. But more than that, his moves required taking measure of the team’s direction — and his own plan.

For Ujiri, doing something different involved taking a series of calculated risks. But more than that, his moves required taking measure of the team’s direction — and his own plan. Why was Ujiri so confident?

  • He believed in his ultimate goal.
  • He believed in his team.
  • He believed in himself.

“Put it on me,” Ujiri told reporters after the Leonard trade, pledging his belief “in this city, this country, this team.”

The result was a Conference Finals victory over the Bucks and the first NBA Finals appearance in Toronto’s 24-year history. Leonard, in particular, proved to be a game changer. And even if the Raptors end up losing to the mighty Warriors, or Leonard signs elsewhere, there is no denying that Ujiri showed real leadership and tremendous ambition.

Business owners know all about risk — and the importance of self-belief. If you are not confident in your plan and decisive in your actions, failure is likely. But sometimes calculated moves pay off in a big way.

Looking again at the Raptors example, Ujiri knew all about Leonard’s upside, as well as Nurse’s capabilities as a coach. He believed in their talents and they came through.

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