From a talent perspective, it appears the Toronto Raptors won the Kawhi Leonard deal. On the court next year, it is widely accepted the Raptors improved their team, even if the long-term impact of the deal is more up for debate.
But as backwards as it may sound, on the court is not the only thing that matters. When grading and determining the merits of a trade, one must take many other factors into account, particularly the salary-cap ramifications. The Kawhi trade involved many, including a couple of unexpected twists not reported until later.