Joe Cronin
Depending on who you ask, Joe Cronin blatantly lied about his intentions of building a title-contending team around Lillard or meant what he said and simply failed to do it. Either way, his inaction pushed Dame to the point where the most loyal player in franchise history requested a trade.
When a deal with the Miami Heat failed to gain traction, Lillard offered to return to the Blazers. Cronin said no, citing a relationship that had soured to the point where Dame simply couldn't be a member of the franchise.
Per Bleacher Report's Chris Haynes, Cronin had the following to say after Lillard was eventually traded to the Milwaukee Bucks:
"Our directions didn't line up. Things didn't work out. We had pure intentions in our desire to build a winner around him. We were just unable to pull it off. I don't think that was a lie. We just couldn't get it done."Blazers GM Joe Cronin
A portion of the Blazers' fan base believes it was, in fact, a lie. Maybe it was, maybe it was sincere, and as he said, the front office "just couldn't get it done."
Regardless of why or how it happened, Cronin will be remembered as the man who traded Damian Lillard.