2. The Toronto Raptors take a risk on Kawhi Leonard
Trading for Kawhi Leonard prior to the 2018-19 season was a massive risk. He was still coming off of his injury fiasco with the San Antonio Spurs and nobody knew what to expect out of Leonard when he returned. Even when the trade happened, the Raptors got some backlash as it was not viewed as a great deal.
Boy, were those critics wrong.
The Raptors traded established star DeMar DeRozan, Jakob Poeltl and a top-20 protected 2019 NBA Draft pick for one guaranteed year of Leonard. That one guaranteed year led to the first NBA Championship in franchise history.
This is arguably the biggest “win-now, figure it out later” trade in recent NBA history and it is one of the rare examples where it worked. While the Raptors did get some luck in winning the NBA Championship, such as the Golden State Warriors falling apart with injury, the fact of the matter is that they are the defending champions and Leonard is a big reason why.
If Leonard would have stayed in Toronto then this undoubtedly would be number one on this list and I would not disagree if someone puts this as the best trade of the decade. You could really put either this or number one at the number one spot and in a few months, the case for the Davis trade being number one is much stronger as well.