2020 - Drafted Malachi Flynn, one pick after Jaden McDaniels
The Toronto Raptors did not disappear after winning the 2019 title despite losing Kawhi Leonard and Danny Green, finishing with one of the league's best records and landing the 29th pick in the 2020 NBA Draft. That draft had one of the strangest first rounds in modern NBA history, with the Top 10 littered with busts and the rest of the round packed with talent, including current Raptors point guard Immanuel Quickley, who went 25th.
For a franchise that loved long, athletic forwards, when Washington forward Jaden McDaniels began to fall it looked like he could make it all the way to the Toronto Raptors with the 29th pick. Instead, McDaniels went one pick earlier to the Minnesota Timberwolves, via a pick traded to them from the Oklahoma City Thunder.
The Raptors then pivoted to take a point guard to develop behind Kyle Lowry. Various mock drafts had them taking everyone from Theo Maledon to Tyrell Terry, but they went with San Diego St guard Malachi Flynn. An accomplished player in college, Flynn has largely been a fringe player in the NBA (50-point explosions notwithstanding).
McDaniels, on the other hand, is set to start a lucrative new contract extension after developing into one of the best defenders in the entire NBA. He is long, quick and anticipates his opponents' moves to cut them off, and he can pick the pockets of the best of them. He has grown into a good offensive player as well and is a cornerstone piece for a Minnesota Timberwolves franchise that just made the Western Conference Finals.
While the Raptors were flush on forwards, landing a talent like McDaniels would have opened up a world of options for them over the past few years.