With The Future Secured, Now What Should The Portland Trail Blazers Do?

Mar 27, 2023; Portland, Oregon, USA; Portland Trail Blazers point guard Damian Lillard (0) watches players warm up prior to the game against the New Orleans Pelicans at Moda Center. Mandatory Credit: Soobum Im-USA TODAY Sports

Now, before we pivot back to the road ahead for the Trail Blazers this offseason, a bit of outstanding “business” first.

As you might have heard, the NBA draft was on Thursday of last week (6/22), and it would appear Joe Cronin and his B-ball Ops cronies brought their “A” game. If I were to grade their assignment, I likely would concur with my Oregon Sports News colleague Patrick Rogers, who doled out an “A” for their performance.

But alas, if ever there was an NBA draft expert (not currently employed by an NBA team, that is), in my humble opinion, it would be Jonathan Givony of ESPN, so I’ll leave the grading to him. With a former teammate of his getting poached by an NBA team, I can only assume they must be doing something right with their draft coverage over at Mothership. 

Take a listen to why Jonny G. thinks the Trail Blazers are the winners of the entire NBA draft.

Or perhaps you prefer someone more analytical in their persuasion. Kevin Pelton of ESPN, who Co-authored the Pro Basketball Prospectus series with John Hollinger and developed both the WARP Rating and SCHOENE System, awarded the Blazers an A-minus.  Here’s why:

“Having moved up to No. 3 via the lottery, the Blazers were in the enviable position of taking whichever of the top three prospects fell to them. Henderson seems to have an unusually high upside for a No. 3 pick, even if he’s not likely to become a star on Damian Lillard’s timetable. If Portland is to thread the needle on improving this season while keeping an eye on the future, it might be thanks to the polished Murray, who has the chance to be an immediate rotation contributor.

“In the second round, the Blazers scooped up Rupert, easily the highest-ranked remaining player in ESPN’s top 100 at that point (No. 20 overall).”


Speaking of John Hollinger (who has worked in an NBA front office), he and Sam Vecenie (The Athletic’s resident draft expert) also weighed in on the Trail Blazers’ performance, but on a pick-by-pick basis.   

Since a subscription is required to read their analysis, I’ll surmise it for you relative to Vecenie’s pre-draft rankings:

  • Scoot Henderson, selected 3rd overall
    • Vecenie’s ranking: 2
  • Kris Murray, selected 23rd overall
    • Vecenie’s ranking: 17
  • Rayan Rupert, selected 43rd overall
    • Vecenie’s ranking: 34

Still not convinced?

Well, I don’t know what to tell you then!

Really this is all just to say, kudos to you, Mr. Cronin, anyway!

While I still believe Cronin’s track record is a mixed bag, I no longer feel it necessary to add the qualifier of “at best”, as in a mixed bag, at best.

My younger brother and I frequently discuss how “stones” are required to win the day in NBA front offices. As the designated leader of said offices, you have to be willing to buck convention, not cave to outside noise or pressure, and be willing to take chances, to roll the dice every now and then.

And Joe Cronin was under tremendous pressure the last two drafts to mortgage the future to appease Dame, especially this last Thursday, but he held firm and netted himself Shaedon Sharpe and Scoot Henderson, both with the potential to be transformative players in their own right. Thereby securing the franchise’s future hopes of championship contention and demonstrating he may have “stones” yet. So again, I say kudos to you, Joe!

Now all that stands between the Blazers and ‘Going For It’ in the here and now is the Chicago Bulls.

The Bulls actually went for it themselves not quite 2 years ago with:

“[T]heir flurry of moves in August 2021 that netted [DeMar] DeRozan and [Lonzo] Ball via sign-and-trade acquisitions, Derrick Jones Jr. in a three-team trade with the Cavaliers and Trail Blazers that sent out Lauri Markkanen and the free-agency signing of Alex Caruso”


The trade with the Blazers is the current sticking point. With the first-round pick in the deal from Portland to Chicago being lottery protected, it still hasn’t been conveyed, which disallows the Trail Blazers from trading future first-round picks. This is something the Blazers should remedy if they hope to build a winner around Lillard.

The timing could be fortuitous, however, with the Bulls growing increasingly desperate by the day after not being able to unload Zach LaVine on some poor unsuspecting sucker, what with his balky knees and gargantuan contract, and having just announced that Lonzo Ball will miss all of next season too.

What Chicago needs, more than anything, to “retool” is a dynamic point guard, and Portland now has 3: Damian Lillard, Anfernee Simons, and Scoot Henderson. That is one PG too many, with Anfernee (and I don’t mean Penny) being the most expendable of the 3, at least in my estimation. So, it’s time for Cronin to play Let’s Make A Deal with the Bulls, and the Toronto Raptors, with Pascal Siakam being the apple of the Trail Blazers’ eye.

No one, in the context of this 3-team deal, is going to want LaVine, so Chicago is going to have to part with DeMar DeRozan, a painful thought for them, I’m sure. In exchange, they’ll receive Simons and Nasir Little, meaning DeRozan would be headed back to Toronto and Siakam to Portland.

While these parameters check the matching salaries box, these players alone are not going to get this deal done. The Raptors are going to want more, potentially a lot more, but if the Bulls would agree to accept 2nd round picks or even 1st round pick swaps in lieu of the first they’re presently owed by the Blazers, then, if I’m not mistaken, Portland could send as many as four 1st round picks to Toronto.

With Kristap Porzingis removed from the chessboard and Draymond Green likely following suit, it’s Pascal or bust, it’s now or never. It’s time for Joe to push all his chips in to see if he can’t get Masai Ujiri (the Raptors’ President of Basketball Operations) to play ball. I think Artūras Karnišovas (the Bulls’ Executive VP of Basketball Operations) could be just desperate enough to want to throw his hat into this ring.

For those of you keeping score at home, this would be but step 2 in the Trail Blazers’ offseason journey, but inarguably the most important. And depending on the treasure trove of draft assets Portland would be sending to Toronto, there may not be a 5th and final step to take.

If Joe Cronin and his B-ball Ops cronies succeed in this trade endeavor, all that there may be left for them to do is resign Jerami Grant and then hope and pray for a reasonably healthy season. But even after all of this, if they fall short in their quest for a championship next season, it’s a shot I think they have to take, especially with their potential-laden (and hopefully) championship-contending backcourt of the future already in-house.

At this juncture, though, they’re playing with house money, they can’t lose, not really. In the event Dame isn’t sufficiently appeased with the efforts of the front office and, in turn, demands a trade, then Joe gets to keep one of his toys in Anfernee Simons, plus whatever Lillard nets him in a trade. If it does come to this, let’s just hope the return is consummate with a player of Dame’s caliber.

While I can see some level of value in fulfilling Lillard’s wishes, in doing right by the best to ever lace them up for the Blazers, not at the expense of maximizing the return for him. If Cronin can do this, if he can get a crazy stupid haul for Dame in a trade, he’ll have earned my trust.

In Joe Cronin, I will trust forevermore!

Well, maybe not forever, but I will certainly give him the benefit of the doubt going forward.

A programming note (cause I don’t know what else to call it): Per the Founder & Editor-In-Chief of Oregon Sports News, “OSN will be out… all the way through 7/17 (Monday), returning 7/18 (Tuesday).”  Meaning the soonest you can expect any new content from me is 7/18. In the meantime, eat up NBA Free Agency for all it’s worth!

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About Jason Poulsen 11 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.