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The Biggest Move the Trail Blazers Could Make with their Draft Pick

The swing may be beyond their reach, but the phone call should be made.

2023 NBA Playoffs - Miami Heat v Boston Celtics Photo by Brian Babineau/NBAE via Getty Images

The Portland Trail Blazers are widely expected to wheel and deal their way to an improved roster this summer, responding to franchise cornerstone Damian Lillard’s desire to contend. The tricky part, of course, is how to accomplish that. Portland has a couple young players, the third pick in the 2023 NBA Draft, and lots of motivation. What could that turn into? That’s the subject of this Draft Day Edition of the Blazer’s Edge Mailbag.


I admire your measured takes but I want you to go extreme for a minute. What’s the biggest deal you could see the Blazers making with their pick and other players to keep Dame? It still has to work and be real, but I want to hear the dream outer edge from the guy who doesn’t go there. I’ll pin my hopes on your answer.

Barb G

My answer to this has varied over the last month, along with most of yours. But I’m intrigued by the Boston Celtics wheeling and dealing over the past 24 hours, gaining Kristaps Porzingis and losing Marcus Smart. They have a hole in their backcourt now. So I’m going to take a flyer.

Let’s presume Jaylen Brown is privately discontented enough that Boston doesn’t like their chances of extending him this summer. He’s a favored target of Lillard and an All-NBA player. He also plays defense! Those are clear green lights for the Blazers to rev their engines.

Let’s also presume Scoot Henderson falls to Portland in the draft because the Charlotte Hornets select Brandon Miller with the second pick.

I’m going to say that Portland calls Boston to offer Henderson and Anfernee Simons for Brown. I can see this deal making both teams wince a little, but also making them nod. That’s usually the sign of a workable swap. If Portland had to throw in some future compensation, I can even see them doing that.

Boston would have a generational point guard in the making, plus Simons to fill in Brown’s position. Getting Brown, everything else in the Blazers’ off-season would be gravy. It’s the fabled move that explains itself, and as good as I can imagine Portland doing.

What about you all? Any dream trades in your pocket as the draft approaches tonight? Share them below, and remember you can always send your Mailbag questions to