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House of Strauss

Two Theories on Why Portland Would Lose the Blazers

Did I Cope on Behalf of the Blazers and Declining Portland?

Ethan Strauss's avatar
Ethan Strauss
Jul 24, 2026
∙ Paid

On Wednesday, I outlined the bull case for cheap new Trail Blazers owner Tom Dundon keeping the team in PDX. Some of my smart subscribers think otherwise. One of them works in the highest tier of the ultra-rich guy finance world. The other has significant local connections. I knew about both these guys before they reached out. They aren’t “randoms.”

Let’s start with the Money Man I’m calling Subscriber A:

I think you are too optimistic about Portland keeping the team. I do not have inside info but believe this is a slight misread of how the “Arb Man” likely thinks about this. I also don’t get the sense that NBA owners are especially interested in expansion given how drawn out that process has been

So I present to you a “Who Says No” style Bill Simmons NBA trade machine alternative:

Uh oh. This doesn’t promise to be the fun kind of Simmons trade from the Portland perspective.

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