Worst: The return package for JR Smith and Iman Shumpert
Phil Jackson found success in the draft, but his trades did not receive acclaim. A few marquee ones were made, but none of them panned out for the New York Knicks, especially the January 2015 trade of JR Smith and Iman Shumpert.
The Knicks brought Jackson on near the end of the 2013-14 season, so he was in the midst of changing this team to his liking and trying to clear space for free agency. So, about halfway through 2014-15, he sent Smith and Shumpert to the Cleveland Cavaliers for Lance Thomas, Lou Amundson, Alex Kirk and a 2019 second round pick.
This package underwhelmed, even in a roster space-clearing move. Thomas remains with the team but does not have a major role, Amundson was strictly a role player in the frontcourt, Kirk never found steady ground in the NBA and the pick was acquired five years in advance. For impactful backcourt players Smith and Shumpert, it did not seem the Knicks received a proper return.
Meanwhile, Smith and Shumpert became quality role players on teams that went to the NBA Finals from 2015-18 (Shumpert was around until 2017), and they won the 2016 championship.
Cleveland succeeded in this deal, when they gave up almost nothing for players who helped them win. New York no longer has Amundson and Kirk, and the 2019 pick will finally convey in June 2019.