4. Neil Olshey
The situation dealt to Neil Olshey at end of last season is arguably the worst possible for a general manager. Not only did he lose four starters of a team with one of the best offenses in the league, but he wasn’t able to convince any big name free agents to sign with Portland despite having the most money to offer.
So what did he do? He signed hungry role players desperate to prove themselves and saved a ton of money for this summer. The direction he took landed one of the most surprising, cost effective, and exciting free agent classes in recent memory.
For a GM that built the Clippers core, you have to be excited about the future potential of the Blazers, this season excluded. On top of the immediate success, he has set the stage for an exciting off season because of money he saved last year. Now he gets to back up his large contracts with how well the Blazers performed this season.
There is no way Portland makes the playoffs without Neil Olshey taking risks and signing hungry players.
Next: Number Three