If we know one thing about Masai Ujiri, it's that he loves challenges. He relishes them and embraces them. Last season, Ujiri traded DeMar DeRozan, a beloved soldier of the north, for a disgruntled, homesick mercenary carrying the name Kawhi Leonard. That trade made the Toronto Raptors immediate title contenders, precisely the challenge Ujiri was up for. With LeBron James out west leading a rebuilding-ish Los Angeles Leakers team, the time was right to make a big splash, and Ujiri did just that.
The challenge of establishing a relationship with Leonard was another uphill battle for Toronto's president, but Ujiri persevered and soon found himself rolling through Toronto's sunny streets, Larry OB trophy in hand.