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 Hannah Foslien/Getty Images)
(Photo by Hannah Foslien/Getty Images) /

#2 Bad move – Evan Turner extension – $70 million over four years.

Two moves seriously hamstrung the Blazers during Damian Lillard’s prime. This was the first one. Evan Turner was a rotation forward who could play make on second units while also defending his position, but offensively, he could never be a starting wing on a playoff team. Olshey needed to surround Lillard with shooting, but instead spent a large amount of his cap space on Turner, who was a non-shooter.

Opposition teams were able to help off him in the playoffs, and by the third year of this deal, he was only playing 13 minutes a night and averaging just 3.3 points a game. Turner, like Leonard, was a great locker-room guy and veteran leader, but giving him $18 million a year was a massive overpay for a guy that was limited offensively.

Olshey traded him to the Atlanta Hawks before the 2019/20 season, and he then retired at the end of the season after playing just 251 minutes that season.

(Photo by Jason Miller/Getty Images)
(Photo by Jason Miller/Getty Images) /

#1 Bad move – Allen Crabbe extension – $74 million over four years.

The second move that blew the Blazers long-term cap space from 2016 onwards, was the massive extension for Allen Crabbe. Crabbe was a nice shooter who had provided good value as a second-round pick with a ten-point per game average in his third year. But, he had only shown that one year of production. His game was also pretty one-dimensional where he didn’t get to the line or the rim often. He wasn’t a great passer, and didn’t force turnovers or rebound well.

Crabbe was a great shooter from three, but this was his only skill. Olshey took a massive punt that Crabbe would go on to be a 20 point per game guy and play a big part in the Blazers future. He got a monster $74 million extension, but lasted just one year as Olshey dumped him to the Brooklyn Nets and brought back the expiring deal of Andrew Nicholson. Because the Blazers were already over the salary cap, this cap space was gone and wasted. Crabbe actually had two decent years with the Nets, but Olshey giving up on him after one year showed that this deal was a bad one.

Also, Olshey had to stretch the deal of Nicholson over seven years at $2.8 million per year, all the way through to 2023/24. These two deals were serious setbacks for the franchise, using this money on two players who are now out of the league.