Winner: OG Anunoby
While the Knicks may have overpaid to acquire Anunoby, the 26-year-old forward will still enter a winning situation in New York, unlike the one he was in in Toronto. New York has made the playoffs in two of the last three seasons and looks to be on their way there again, while the Raptors are expected to miss the postseason for the second straight year.
Anunoby will be able to slide in as the Knicks' starting small forward and operate as a third option, similar to how he often does in Toronto. However, Anunoby will likely have some easier scoring opportunities playing for a much better shooting team that can space the floor and open up driving lanes.
Jalen Brunson and Julius Randle are also likely better playmakers than Pascal Siakam and Scottie Barnes, Toronto's two stars. Additionally, Anunoby's agent, Sam Rose, is Knicks' president Leon Rose's son, meaning Anunoby will enter an organization that likely knows him and his game well.