2015
Olshey dealt Will Barton, Victor Claver, Thomas Robinson and a 2016 first rounder for Arron Afflalo. Hindsight is always 20/20, especially in this case.
Who knew Wesley Matthews would have torn his achilles? And, if he hadn’t, this trade could look totally different.
The Blazers were 41-19 when Matthews went down, and had the 4th best record. They had won five straight and were on the heels of the Grizzlies.
Afflalo could have remained as the sixth man, keeping that formidable five in tact and the Blazers could have had a deep playoff run.
During the upcoming summer (when Aldridge departed), Nicolas Batum was dealt for Gerald Henderson and Noah Vonleh. Olshey foresaw that Batum was in for a hefty payday and opted for the younger career arc to go with Lillard.
He obtained a veteran presence in Hendo and, at the time, a 19-year-old Vonleh.
Fast forward to the present day, Batum is averaging 15-6-6 on 40% FG and earning $100 million over the next four years.
Whereas Vonleh is still only 21 and not clogging the cap has shown he can be a long-term piece.
Olshey also dealt Steve Blake and the rights to Rondae Hollis-Jefferson for Mason Plumlee and Pat Connaughton.
RHJ is a solid role-player, Plumlee played a crucial role in the 2016 first round and was a key piece in The Transaction this past season.
In the same summer, a top-55 protected second rounder was exchanged for Maurice Harkless. Talk about acquiring something for nothing. Harkless remains a valuable piece and continually improves at the age of 24.