Many factors at play for Ujiri as Raptors contract decision draws near

The last time Masai Ujiri was a pending free agent, his next move was decided at a posh mountain retreat in Vail, Colo., a two-hour drive west from Denver where he was in the final year of his contract as general manager of the Nuggets.

He met there with Tim Leiweke, then the decidedly up-tempo chief executive officer of Maple Leaf Sports and Entertainment. At the time, Leiweke was in the midst of a lightning-speed makeover of the company that owned the Toronto Maple Leafs, Toronto Raptors, Toronto FC and a range of other holdings, but no championship trophies.

Leiweke’s contacts in the NBA and across the sports industry in North America ran deep, and he’d determined in the spring of 2013 that Ujiri was the person he needed to right the ship that was the Raptors, seemingly drifting aimlessly into mediocrity in what turned out to be the final days of former Raptors president Bryan Colangelo’s run with the club.

Ujiri — who had worked as a scout and assistant GM for Colangelo in Toronto before taking the GM position with the Nuggets — had led Denver to three consecutive playoff appearances and a franchise record 57 wins in 2012—13. He was a star on the rise.

“We talked to other people,” said Leiweke, who revamped the front offices of all three of MLSE’s clubs in his brief-but-impactful 30-month stint in Toronto. “But we had done our homework, and…

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