Portland Trail Blazers: Ranking Neil Olshey’s best and worst moves as GM

Neil Olshey and Damian Lillard, Portland Trail Blazers (Mandatory Credit: Troy Wayrynen-USA TODAY Sports)
Neil Olshey and Damian Lillard, Portland Trail Blazers (Mandatory Credit: Troy Wayrynen-USA TODAY Sports) /
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(Photo by Jim McIsaac/Getty Images)
(Photo by Jim McIsaac/Getty Images) /

#5 Best move – traded Steve Blake and Rondae Hollis-Jefferson to the Brooklyn Nets for Pat Connaughton and Mason Plumlee.

Though this move might not seem like much on the surface, giving away a rookie Rondae Hollis-Jefferson and an aging Steve Blake for strong role players in Pat Connaughton and Mason Plumlee, set the stage for moves down the line and the basis of today’s team.

Olshey selected Hollis-Jefferson with the 23rd pick in the 2015 Draft, and instantly packaged him with Blake to bring back Connaughton and Plumlee. Connaughton only provided minimal backup guard play for the Blazers, but has since gone on to be a rotation member of the contending Milwaukee Bucks. Plumlee was the main piece in this deal, as he played 136 games for the Blazers, averaging an impressive 9.9 points, 7.8 rebounds, and 3.2 assists.

Plumlee was then used in a future deal that netted a massive upgrade and a first-round pick. A nice piece of business that we will detail further down the list.

This was an example of Olshey making a smart move when it came to a player trade.

(Photo by Abbie Parr/Getty Images)
(Photo by Abbie Parr/Getty Images) /

#4 Best move – drafting Gary Trent Jr with the 37th pick in the 2018 Draft

Olshey may not always get it right when it comes to signing players to long-term deals, but he has a great record of selecting players in the second round of the draft.

Gary Trent Jr was probably the best of these picks, using the 37th pick to select him in 2018.

He impacted the team pretty quickly in his second season, averaging 8.9 points per game in 2020, including around 17 points a game on 50 percent from three in the bubble.

The pick of Trent was also impressive as the Blazers didn’t actually have a second-round pick in 2018. Olshey traded two future seconds and some cash to get this pick and select Trent.

Trent, in 2021, was even more impressive, averaging 15 points on a game on 39 percent from three. All the while, Trent has played impressive man defense and shown great toughness and maturity for his age. Sadly, Trent’s impressive play and pending restricted free agency meant that he was moved to the Toronto Raptors as the Blazers knew he was likely to get big offers from other teams. They returned an excellent player though, in Norman Powell, who can be part of the playoff run and play the small forward spot for the team.

An excellent return for what started with a first-round pick.