General Manager Joe Cronin is not new to being dogged for a perceived lack of asset management acumen.
His detractors always have the same two arguments: Cronin lied. He never wanted to build around Dame, he just wanted to rebuild without saying he wanted to rebuild. The Robert Covington and Norman Powell trade as well as the CJ McCollum trade have served the evidence. The transfer of talent was so lopsided, you wonder if basketball reasons could come back in our favor.
But they also serve the evidence for the argument against. The unfortunate truth of the matter was a lack of cap space flexibility led to a lack of trade leverage and this perceived lack of leverage meant that any trade to find said flexibility would come at a talent premium if the Blazers wanted another shot at building a contender around Lillard.
Make no mistake, my pedigree chums: Joe Cronin wanted to build a contender around his franchises’ best player—it’s the most straightforward strategy to selling out the Rose Garden night-in and night-out during the winter rains. One might deem it foolish not to try, even if the key decisions for making it possible within a sustainable timeframe needed to happen four years prior to his promotion. But not planning for the very real possibility that it could happen would have also constituted industrial malpractice.
Here’s a basic truth: all things end the same way. Slowly, at first, and then all at once. Such was the case for the Damian Lillard trade.
Here’s another basic truth: small markets need draft picks in order to build. I’ll say it again: small markets need draft picks in order to build. Whether to draft or trade, cashing in picks is the only way to improve. Knowing when to do either is paramount to contention. And Portland’s capacity to trade picks was paralyzed by an ill-fated trade for Larry Nance Jr. One 1st rounder in 2021 and one lottery-protected 1st rounder anywhere from 2022 all the way to… 2028?!? Goddamnit, Olshey.
On that irritating reminder, the last basic truth: Cronin and Lillard’s honesty about building a contender in Portland put them in opposition with reality. Specifically the reality that Lillard was aging. The calculus is simple: as Lillard’s age became factor, so rose the higher the price of acquiring of talent to help Lillard. This reality meant the rest of the association knew that refusing to help the Blazers build that contender could potentially place them in the running to acquire Lillard.
It wasn’t malicious noncompliance, but it was deliberate noncompliance. A strategy that frustrated any effort to build something around Lillard. Ironically, Lillard more or less thwarted such noncompliance by requesting a trade to Miami and only Miami.
To some, the cost of retaining Lillard began to outpace the expected return on trading him. Maintenance began to compound on depreciation. In 2025, Lillard will start raking in the first $55 million of his $120 million supermax extension and whoever held his contract would be begging Pat Riley for Tyler Herro, two picks and the dug up corpse of Kyle Lowry. That’s not a dig at Lowry, he’s probably just not going to be in the league by then, or at least, not at a $40 million value.
The current deal must be measured against the whispered deals for Siakam, which stood at Anfernee Simons, Shaedon Sharpe and the #3 pick that would become Scoot Henderson. That’s a steep price to help Lillard in the immediate period and it was just a one-off, as there was no promise Siakam would re-sign the next year. Ultimately the organization would have bought a year of darkhorse contention and vastly depleted their already paper-thin depth in a market that does not attract free agents and sold on any future prospects.
It’s a situation similar to the Golden State Warriors or the Los Angeles Clippers. Expensive names, probably fighting for second-place. There’s no shame in making such a swing for the franchise icon, but the lack of flexibility would have ended the situation even more poorly than the end of the Lillard/McCollum/Nurkic core.
And the organization was quite ready to do it, had Lillard not demanded a trade. This is how things change: slowly, at first, and then all at once.
In a way this trade would have been unnecessary had Lillard not said anything. But by requesting it to only team, he gave the Blazers a “moral” leverage more or less, to provide themselves the best return even if its not some field of the cloth of gold. And yes, that’s the kind of reference you can expect from a French major who likes basketball.

However, that was an improvised line. In my notes, I found my relating the situation to my love of the Foundation series by Isaac Asimov. It was a matter of course to explore sci-fi from classics to contemporary for me, and, not to dog Frank Herbert here but: if I’m going to read the Dune series, then I want to start with the series that forms the backbone of Dune.
Anyways, in the Foundation series the Galactic Empire of Humans is in terminal decline. After a millennia of opulence, the edges of the Empire had begun to fray and would soon tear apart its hegemony over the Milky Way. A dark age is inevitable, concludes Hari Seldon, the psychohistorian who studies the movement and behaviours of human social structures with the view of a mathematician. In his models, the Empire would effectively last for another 300 years before a Dark Age of ten thousand years commenced.
In order to head off this era of blood, Seldon convinces the Emperor to send him, his scientific followers and their families to the planet Terminus at the far edge of the Milky Way in order to found the titular Foundation that would write an encyclopaedia of all human knowledge and shorten ten millennia to just one. For the Emperor, it was a win-win situation: he removed political dissidents and those dissidents potentially add to his legacy as a just and wise ruler. Had he chosen otherwise, he would have preserved the Empire in its stagnancy for a short period of time at the cost of exponential disaster.
I maintain this the calculus behind Joe Cronin’s decision making in the past two years, starting with the summer leading up to the 2022 NBA Draft. Give up a king’s ransom to resume an era of diminishing returns with Lillard—the Empire—or pick a player that could grow as the Empire crumbles, Terminus. Cronin still maintained the option to sell on Terminus and continue pouring resources into the Empire, but now he had the insurance.
In the end, he planted the seed and that seed became Shaedon Sharpe and Scoot Henderson. Now they are on their own, a lonely Foundation against the Galaxy. Or they would have been, had Cronin not turned over the Lillard, Nurkic, Little and Johnson contracts for Deandre Ayton, Robert Williams III, Malcolm Brogdon, Toumani Camara and potentially five future high lottery picks.
The benefits of a return this size allows them to pursue a path of least resistance. If they’re bad, they’re bad and they can aim for a high lottery finish or trade away Grant, Williams, Brogdon and Simons for even more picks on the spread.
If the Blazers manages to compete for a play-in spot, however, their talent at center has improved dramatically. They now have some of the best defensive bigs in the league who can apply excellent rim-pressure, with a talented young backcourt and enough veteran leadership to give unsuspecting teams the rope-a-dope.
The Blazers are no longer threading a needle between two timelines. Now, they are a young, hungry team allowed to figure it out win or lose. It’s how you build the next era in a franchise: slowly, at first, and then all at once.
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