Summer of 2016
Notably, the Blazers struck out on Hassan Whiteside and Chandler Parsons, then opted to sign Evan Turner to a four-year, $70 million contract.
Before we dive into the gritty details, let’s look at this summer broadly.
The Blazers had full Bird rights (cap holds and qualifying offers) on Harkless, Crabbe and Meyers Leonard.
With all that in mind, the Blazers had carved up max-level cap space. With the aforementioned Whiteside and Parsons going elsewhere, Olshey and the Blazers had two options.
Two tricky slopes
Either overpay a mid-tier player (Turner) while re-signing Harkless, Crabbe and Leonard or relinquish the cap room and just retain Harkless, Crabbe and Leonard.
The option of just rolling over the cap space and not bringing any of those three back is inconceivable. Signing only one or two meant giving up max-level room, and therefore not acquire anyone else meaningful (the Blazers have to overpay, remember).
Letting them walk for nothing is also poor asset management and not the culture-building message you want to send to Lillard and McCollum.
As we all know, Olshey went for option No. 1: use the cap space while it was available on Turner (and Ezeli), match the offer sheet on Crabbe while also re-signing Harkless and Leonard to cap-friendly deals.
Turner and Ezeli were first signed in order to use the cap space remaining, then the retention.
Leonard was re-signed to a fraction of the cap (10% aka old mid-level equivalent) and then the Crabbe decision was made.
Either you let Crabbe (and his 44.4% 3-point shooting) walk for nothing (no cap room for replacement) or you pay him. So they did. Soon after, Harkless was re-signed for 10.3% of the cap.
Changing cap makes deals look worse than they actually are
Skilled wings have become a premium in the NBA as of late, and this is part of the reason behind Turner (playmaking, size, defence) and Crabbe (elite shooting, size).
The salary cap was projected to rise $14 million, where in reality it only rose $5 million.
Consequentially this lowered projections going forward, which cramps the ceiling in which Olshey and the Blazers can maneuver under via trade.
This resulted in the Turner and Crabbe deals looking worse off.
Related Story: The Ringer on Portland's cap situation pre-Crabbe trade
Instead of being roughly 16% and 17% of the cap, they now sit at 18% and 19% respectively.
Leonard could also help his case by not seriously under-performing even though his contract is numerically a bargain in today’s market.
Olshey was under the impression that the cap would continue to rise in conjunction with the market premium for wings.
The only criticism I might have is that even at the time, the Turner contract was a bit much. He is 28, likely won’t get much better and even Turner himself was “shocked“.
Although Blazer fans don’t have to worry about paying the tax directly, it does hurt their financial flexibility down the road.
Offering Turner less with the risk of him declining would have been better.
But, once again, hindsight is always 20/20. Disregarding the Turner contract would also mean the Blazers would only be over the luxury tax by $2.36 million.