Since June 2012, Neil Olshey has maintained his position of general manager for the Portland Trailblazers. He oversaw the draft selections of Damian Lillard and C.J. McCollum, while also helping revitalize Carmelo Anthony's basketball career last season. Yet currently, he is under investigation for workplace misconduct, which could ultimately end his reign in Portland. There has been speculation that if Olshey's firing were to occur, Danny Ainge would be the top target to replace him.

The former President of Basketball Operations for the Boston Celtics would be an enticing candidate for the Blazers. His ability to garner draft capital at a high level, along with shaping the right culture, could be just what this Portland organization needs in order to be more successful in the playoffs. Additionally, Ainge has a personal connection with the Blazers, as he grew up in Oregon. Though there hasn't been true interest from his part, the signing could make sense for both parties.

With employees and staff members of the Blazers speaking out on Olshey's workplace misconduct, owner Jody Allen has hired a private team to run an independent investigation, but there is a chance that this could take several weeks to sort out. Yet this situation seems to not be in the favor of the long-time Portland GM as former players and employees already have evidence against him.