Leonard and his advisors have since rejected a $20 million offer from the Jordan brand to extend his association with them and ruled out the possibility of a five-year, $221-million extension by making the move from San Antonio to Toronto.
The Raptors took DeRozan with the ninth pick in the 2009 Draft, during which time DeRozan became the franchise's leader in several categories, including games, points and minutes played.
DeRozan himself was shocked by the news.
DeRozan was reportedly told earlier in the summer he would not be traded.
"In my job, I always have to assume we're going forward with the team that I have", he said, via Bleacher Report. If there was a miscommunication there, I do apologize to DeMar and his family and his representation.
Ujiri said that he struggles with the human side of the business, but ultimately feels good about the trade.
But he said he regretted perhaps indicating to DeRozan that he wouldn't be traded. I take responsibility for that. "Our city. Our ownership", Ujiri said.
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The Raptors have an incredible fan base and a roster that could contend for an NBA Finals spot. On paper, forcing his way away from the best-run franchise in the National Basketball Association is a real head-scratcher.
Still, there are reasons for concern.
On the other hand, the Raptors present a fresh start for Leonard, and his presence adds anticipation to their squad for the 2018-19 season.
And while many predict Leonard will bolt from Toronto, not everyone is convinced.
"I think there's a lot to sell here", Ujiri said. "We have everything here except a championship". "I don't think we lack anything in this city".
Ujiri said Friday the fans were not forgotten in the trade decision but it's "hard to satisfy everybody". Ujiri disputed rumors that Leonard has no interest in playing north of the border. Leonard posed for a picture with Raptors lead executives Masai Ujiri and Bobby Webster at the BioSteel Centre, while Green hung out with the Raptors Uprising NBA 2K League team.