It’s Time For The Portland Trail Blazers To Raise The White Flagg (Pun Intended)

First, what my brother and I call non-breaking breaking news.

  • Damian Lillard has released his new album.
  • Jusuf Nurkic has put his home up for sale.

Otherwise, all is quiet on the Portland Trail Blazers Front. An uninteresting but positive development as far as I’m concerned. The reason being?

This silent treatment very well could mean Joe Cronin is prepared to use the only leverage he really has in his present standoff with Dame and his agent. At least in theory anyway, it would seem Joe is willing to bring Lillard back next season rather than trade him for a return that is NOT commensurate with a player of Damian Lillard’s stature – NBA 75th Anniversary Team, All-NBA, All-Star, etc., etc.

Now onto actual relevant news, albeit more nuanced as it relates to Portland. But don’t be dismayed; I’ll bring it all full circle.

As reported by ESPN’s College Basketball Insider Jeff Borzello (@jeffborzello), “Cooper Flagg, arguably the best prospect in high school basketball, announce[d]he’s reclassifying from 2025 to 2024.”


Meaning he will be draft eligible in 2025. Great, right!?

So long as the Trail Blazers are in the lottery and thus are in on the Cooper Flagg Draft Sweepstakes. Here’s why you should care, per ESPN Draft Insider Jonathan Givony (@DraftExpress):

“Standing 6’9, with outstanding mobility and quickness getting off his feet, Cooper Flagg is first and foremost a devastating force defensively, capable of guarding 1-5. He’s an excellent passer and finisher, a developing shooter, and makes the game easy playing a winning style.” (

If this skillset descriptor seems even vaguely familiar, first and foremost, thank you! If it’s ringing any bells, it may be caused somewhere in the recesses of your brain. You recall having read something like this before. Maybe about Draymond Green and how he would be the perfect player for the Blazers to add to the spirit of “Going For It” next season?  (

But alas, Draymond opted out of the last year of his deal and, after becoming a free agent, re-signed with the Warriors. I liked him for Portland much more on a prove-it deal (in the last year of the contract he opted out of) than the four years and $100 million he ended up getting. In my estimation, he represented too great of a risk age and health-wise for the Trail Blazers to justify making a similar financial commitment, especially since trading Anfernee Simons would’ve been a part of the calculus.

Now if Green helped lead the Blazers to a championship next year, I wouldn’t have stood in their way from resigning him to whatever ridiculous sum. Such a contract would age much better after a parade, but I digress…

Wouldn’t it be better to focus on the future, on a younger/hungrier player with a similar skillset? Do you see where I’m going with this?

An injury notwithstanding, Cooper Flagg, however unlikely, could go the way of Emoni Bates and fail to live up to the hype. But, as of this moment, a player with a Draymond Green ceiling and an Andrei Kirilenko floor is just the sort of difference-maker the Portland Trail Blazers should be positioning themselves to draft.

There’s just one problem, one leftover item of business from the previous regime…

…that pesky trade for Larry Nance Jr.  Pesky cause the Trail Blazers could’ve had Lauri Markkanen instead, which in turn would’ve made everyone in Rip City feel a whole lot better about Portland still owing Chicago a lottery protected 1st round draft pick (the leftover business item).

What’s worse is a powerful argument could be made that this trade (indirectly obviously) served as the impetus for Dame requesting a trade. It has proven rather difficult for Cronin to acquire another impact player beyond Jerami Grant without having the sweetener of a 1st round pick or picks at his disposal. And until the pick is conveyed to the Bulls, the Blazers will continue to be hamstrung, at least through 2028, after which the pick becomes a 2nd rounder.

The good news, barring Portland making a surprise return to the playoffs two seasons from now, is they won’t be precluded from the Cooper Flagg Draft Sweepstakes, thanks to the lottery protections. [It would seem Neil Olshey learned from his ill-fated trade of Baron Davis and a 1st round pick (without any protections) to Cleveland. The latter ended up being Kyrie Irving, drafted 1st overall by the Cavs in 2011, ouch!]  The not-so-great news, unless they remain in the lottery through the 2027-28 season, the aforementioned trade will cost them a 1st round pick.

But what if there was a way to recoup this pick from Chicago while also trading Lillard to his preferred destination, the Miami Heat? Or, in a more pie-in-the-sky scenario, what if there was a way for the Trail Blazers to run it back with an appeased and, dare I even say, happy and content Damian Lillard?

I am considerably less enthused by the latter scenario, assuming Dame would even consider relinquishing his trade request. As you’ll see, the potential costs for going this route are pretty high, maybe even alarmingly so. But I will let the heartstrings of your fandom pull you in whatever direction they most desire.

Here is a trade I’d like to see happen:

The Blazers receive:

  • Patrick Williams from the Bulls -&-
  • Kyle Lowry & Nikola Jovic from the Heat

Lowry is on an expiring deal and would be a great mentor for Scoot, Sharpe, and Simons.

  • Plus, picks, picks, & more picks of the 1st round variety (including swaps), but most importantly, recouping their own pick from Chicago.

Once Lillard is traded, they will be in full rebuild mode, so their own picks will likely prove to be the most valuable, especially as they join the various player draft sweepstakes over the coming years. Cooper Flagg is but the first. Other identified elite prospects to keep tabs on include Flagg classmate Airious Bailey and 2026 draftees Cameron Boozer (son of Carlos) and A.J. Dybantsa. 

(, subscription required)  

The Bulls receive:

  • Tyler Herro & Jaime Jacquez Jr. from Miami, the former being their PG heir apparent to Lonzo Ball.

Speaking of which, Ball, I mean, they also get out from under his contract two years early.

The Heat receive:

  • Damian Lillard from Portland -&-
  • Lonzo Ball from Chicago

The cost of doing business for Miami is eating Ball’s contract. But all they’re really doing is punting down the road (by one additional year) the cap relief they were going to get from Kyle Lowry’s expiring deal.

This, my friends, is how you take lemons and make lemonade!

Whereas possibly retaining Damian Lillard may be more lemons than lemonade, but who knows? Maybe Chef Cronin can craft a lemon meringue pie out of this pie-in-the-sky standstill scenario?

And here is the trade I’m less enthused about:

Portland receives:

  • Andre Drummond, Lonzo Ball, & their 1st round pick back from the Bulls

Chicago receives:

  • Jusuf Nurkic & Keon Johnson from the Blazers

So, the Trail Blazers are giving up a starting caliber center in Nurk for a serviceable one in Drummond, advantage Bulls, and eating Ball’s contract, again advantage Bulls. But they are recouping their pick, which would free up “The Chef” to land an impact player to appease Dame. The danger of such a maneuver is the cost, with Portland already starting at a deficit for making this trade. The costs only go up from here and include embedded opportunity costs if they have to part with Simons to land such a player.

I think I’ll stick with lemonade, thank you very much, however enticing the meringue pie may be. But this is a judgment-free zone, so follow your heart wherever it may lead. Just expect a nosebleed if you’ll do anything to retain Lillard cause the Blazers will have to pay out the nose even to hope to have the chance to make this happen.

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About Jason Poulsen 18 Articles
As a former collegiate basketball player, with a great deal of emphasis on the former, my passion for the game has since led me on quite the journey. Writing for the Oregon Sports News, along with the effort I’m putting in to finally get a long ago developed proprietary basketball performance analytical tool off the ground, represent full circle moments. There have been a multitude of stops & roles along the way, the pertinent ones being Assistant to Director of Basketball Operations, Basketball Operations Assistant, NBA Draft Statistical Analyst, & Sports Writer, & the less pertinent – Store Manager, Lids Sports Group. I suppose one hasn’t really lived unless they’ve worked in retail or so I’ve told myself.