On July 18, 2018, Toronto Raptors president Masai Ujiri shocked the NBA when he pulled the trigger on one of the gutsiest trades in recent memory.
Ujiri took franchise cornerstone DeMar DeRozan -- a four-time All-Star who pledged his loyalty to the NBA's only Canadian franchise, famously saying, "I am Toronto" -- and sent him to San Antonio for the disgruntled and injured Spurs star Kawhi Leonard.
Specifically, the player Ujiri was getting was a former Finals MVP coming off a bizarre breakup with one of the NBA's best-run franchises after a season of miscommunication and mystery surrounding his injured quad. Ujiri did not know which Kawhi Leonard he was getting: Was he getting the Kawhi Leonard many thought to be an MVP candidate before his injury? Or was he getting a drastically reduced Kawhi? The one guarantee he did have was that whatever player he was getting, he would get him for one year and then all bets were off, because Kawhi is due to be an unrestricted free agent in the summer of 2019 and it had been reported again and again that he wanted to return to his childhood home in Southern California.
This was the definition of an NBA executive going for it. Remember the Tribe Called Quest song, "Midnight," which features the lyric, "Scared money don't make none?" Oklahoma City Thunder executive vice president Sam Presti quoted that line when he spoke about the risk the Thunder took in trading for one season of Paul George. That was the model that Ujiri hoped to emulate: Trade for one year of a superstar, treat him like royalty, win at a high level, and convince him to stay.
Ten months after Ujiri pushed all his chips to the center of the table, Saturday night was turning into a Sunday morning in Toronto, and the streets of the city were going wild. The Raptors had just dispatched the team with the likely MVP and the league's best regular season record, Giannis Antetokounmpo and the Milwaukee Bucks, in six games of the Eastern Conference finals to take the franchise to its first NBA Finals appearance in a quarter-century of existence. Cars honked their horns. Fans screamed; two of them stood out of a sunroof of a car that was doing donuts on Bay Street right beside Scotiabank Arena. Fred VanVleet could hardly drive his car through a throng of Raptors diehards who were shouting their postgame appreciation.