Portland Trail Blazers: What Neil Olshey’s scouting tendencies could tell us about the 2020 NBA Draft

The Portland Trail Blazers will be entering an unpredictable 2020 NBA Draft this fall. Can Neil Olshey’s drafting history offer any hints on drafting plans?

At the start of this generation, NBA front offices across the map — the Portland Trail Blazers included — were hooked on one phrase above any other: “upside.” Tangible, on-tape talent took a backseat to upside, and traits like work ethic and character were somewhere in the trunk.

Perhaps Bill Simmons said it best in chronicling the mentality at the time of the 2003 NBA Draft: if upside were a drug, every GM would have been in rehab.

Thanks in large part to an emphasis on ball movement and chemistry, the term “upside” no longer resides atop of the totem pole in today’s draft vernacular. The new chic, go-to tag is “fit.” How does a player fit into a scheme? In the locker room?

Thinking about the Blazers, they are a team with more than a few minor weaknesses on its roster, which makes it difficult to project if they will prioritize fit ahead of talent and upside.

But, can we learn anything from Blazers executive Neil Olshey’s past to glean out answers in the future?

Blazers head coach Terry Stotts had a telling answer to that question, when asked on NBC Sports Northwest’s Talkin Blazers with Channing Frye. Olshey’s philosophy historically points to overall talent taking precedence ahead of fit.

"“I think in general, Neil is a big believer in talent, you know. But, we’ve had success in the second-round, and basically with some four-year guys. I mean you look at Jake Layman and Pat Connaughton, and those guys in the second round.Those guys ended up … our success rate with second-round guys, you throw in Allen Crabbe and Gary Trent Jr., as you mentioned, those guys were developed into NBA players, and are having NBA careers that maybe you didn’t project when you got drafted.”"

Stotts added that in the lottery and the first round, Olshey focuses on talent over positional need. Using that baseline, should we potentially have fears about the Blazers drafting another unheralded guard who can score points in abundance, instead of say, a switchable 3-and-D wing?

Olshey isn’t oblivious to team needs, and won’t be in the 2020 NBA Draft. In fact, of the 14 players he’s drafted in his tenure since 2012, eight of them have been reputable players around the Association (nine if Nassir Little makes strides). But here’s a quick synopsis of recent history.

Take the summer of 2018 for example. Portland selects Anfernee Simons with the No. 24 pick. Sports Illustrated’s Ben Ladner called it a potentially “unnecessary risk given the others on the board,” and called “moderately surprising” by The Oregonian’s Joe Freeman. Among those still undrafted at the time: Landry Shamet, Devonte’ Graham, Jalen Brunson, Mitchell Robinson … and a bad, bad man by the name of Gary Trent Jr.

This isn’t to say Simons wouldn’t be putting up Graham-type numbers in a free-rein system like Charlotte’s. The best development comes through repetitions. But the Blazers had to know what they already had in McCollum and Lillard, no? Based on the concrete numbers. It feels proven that they’ll take talent over fit or need, as Stotts estimates.

Even with the selections that worked, Olshey’s mindset has been tried and true. In 2013, the Blazers went out and snagged a pair of two-guards in CJ McCollum and Allen Crabbe, even with Wesley Matthews providing consistent, reliable minutes, and Will Barton blossoming at the tail end of an injury-riddled 2012-13 season.

The 2017 NBA Draft also offers a riveting case study. This is the Draft in which the Blazers and Kings did a swap that gave the Kings the No. 15 and No. 20 picks (which became Harry Giles and Justin Jackson), allowing the Blazers to take Zach Collins.

Before Jackson forgot how to shoot — his 3-point percentage dipped below 30 percent for the first time, and subsequently got out on Bleacher Report’s 2021 “bust watch” — one could’ve made the argument that the Blazers could have used assets like Giles and Jackson ahead of Collins, given the 2-for-1 nature.

Funny enough, Giles has been linked as a player the Blazers should try to sign this fall. For all of the injury concerns, Giles has only played in 50 fewer games than Collins. Everything considered, though, the Portland Trail Blazers have to love what they’ve gotten out of Collins when he has been healthy, though.

Along with the upsi— um, talent-over-fit mindset, it also showcased Olshey’s newfound propensity for selecting younger talent. When the 2019-20 NBA season tipped off, Nassir Little was the fifth-youngest player in the NBA.

One year prior, Simons held that same distinction, and was the youngest to be drafted in Portland Trail Blazers history. If the Blazers are thinking youth, perhaps Florida State’s Patrick Williams, or someone of that kind in the 2020 NBA Draft.

All of this provides a potential roadmap, for what the Blazers could do in the 2020 NBA Draft. But if we’ve learned anything, it’s that Olshey, by nature, isn’t an easy figure. The dice will be rolled. And perhaps that is what makes the process that much more fun.