Sports are about moments. They’re about legacies. They’re about competition, camaraderie and maybe most of all, they’re about lasting impressions that leave fans loving, loathing and remembering how they felt years—if not decades—later.
Kenny Wheaton has “The Pick.” Brandon Roy has “The 4th Quarter.”
Damian Lillard has “The Shot.” Marcus Mariota has “The Rose Bowl.”
If Portland Trail Blazers general manager Neil Olshey has become known for anything during his time in the Pacific Northwest, it’s his drafting of Lillard—a risky yet brilliant selection that brought the city a franchise player it could be proud of both on and off the court. But what he’s maybe really become known for is his backcourt hubris. He’s content with “competing” in the first round of the playoffs as long as he has one of the best guard tandems in the NBA. He’s arrogant to the point that fans and media alike now question when and how often he tells the truth. His unwillingness to break up Lillard and CJ McCollum has put the Blazers in a position where they’re neither good enough to win a title nor bad enough to earn a top lottery pick.
But while Olshey may be the topic of debate among fans in Portland, the GM has a quality about him that too often goes unrecognized. Because the truth is, while most think of swinging and missing as a bad thing, it can show that management has the guts to make the right phone calls even when the results don’t show.
Paul George? Swing and a miss.
Carmelo Anthony? Not so fast.
DeMarcus Cousins? Was never gonna happen.
Kawhi Leonard? Sorry, please leave a message.
Olshey has yet to prove he’s a closer, but he has proved he can and will put himself out there. He just hasn’t put himself—or his roster—out there far enough.
If Olshey is smart, he’ll pick up the phone and call the Minnesota Timberwolves, who are not-so-suddenly dealing with a discontent star in Jimmy Butler. Butler has reportedly requested a trade, and while his short list of preferred teams includes (and is apparently limited to) the LA Clippers, Brooklyn Nets and New York Knicks, we wouldn’t call it “shooting your shot” on the Interwebs if rewards came without risks.
Making the phone call is Step 1, and it’s one Olshey is familiar with. Because Olshey is intelligent (whether you want to believe it or not), he’ll avoid showing his hand up front by trying to convince Tom Thibodeau to give up on Butler without including CJ McCollum. Portland can offer a package surrounding draft picks, Evan Turner’s nearly-expiring contract and Mo Harkless or Zach Collins. (FWIW, Collins may be considered untradable at this time. He shouldn’t be, but he may be.)
But when Thibs and Co. come back with the same response Olshey has heard from Indiana, New York, New Orleans and San Antonio, he needs to adjust. Remember Willie Taggart? The guy who proved in one year at Oregon that an inability to adjust your scheme is a recipe for disaster and is now 1-2 at Florida State? Look no further to find an example of needing to change your scheme when things get stale.
If giving up McCollum is what gets this deal done, Olshey needs to make it happen. The risks are apparent: Trading away Lillard’s best friend is less than ideal; bringing back a player who has yet to be content with a professional franchise is problematic.
The fact that Butler can become an unrestricted free agent next summer is enough to make most teams shy away before ever dialing 1-800-GIMME-JIMMY.
But this is Olshey’s shot. Best-case scenario, you bring on Butler as the final piece to the triumvirate the Blazers desperately need. Worst-case scenario, you give up on McCollum being the second banana on a championship team and Butler bolts in 2019 giving you legitimate cap space and potentially a high lottery pick in 2020.
Although it may feel counterintuitive to say that that losing both McCollum and Butler in the same calendar year is a positive, it’s better than being stuck in the middle. Being great is great, being good is good, but being bad is better than being mediocre.
If Olshey wants to be known for anything in Portland—if he wants his signature moment to evolve beyond a draft pick more than six years ago—now is his chance to shoot his shot. He needs to pick up the phone, and he needs to do whatever it takes to get Portland a star.
Otherwise, his signature moment of drafting Lillard may be his only resume booster as he looks for a new job outside Rip City.
