This is part of a four part series on the Trail Blazers 2025 offseason. You can read all the previously published and future parts via the links below.

Part 1 – Part 2 (You are here) – Part 3 – Part 4 (Coming soon!)

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I have an honest question for those in the back wringing their hands about the salaries on the Portland roster.

When was the last time the Trail Blazers ever managed to maximize cap space and lure a top free agent to the Pacific Northwest? Here’s the three biggest to my memory: Andre Miller (decent), Carmelo Anthony (fun, but old) and Evan Turner (massive overpay). Not quite the stuff of excitement.

Which is all to say that I still can’t believe that Damian Lillard is a Portland Trail Blazer again, and that he is simultaneously one of the greatest draft picks and one of the greatest free agent signings in franchise history.

This factoid cannot be real. I have a whole timeline detailing my depression era side-by-side with Lillard’s departure to and tenure with the Milwaukee Bucks, but for the sake of these thoughts, I’ll keep it simple.

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When Lillard was ruled out with a deep vein thrombosis in March, my first reaction was a simple “damn.” It just sucked to think that this pairing of Lillard and Antetokounmpo was not being given a real chance for health. And yet, it did not surprise me when came back for the playoffs. That’s just the kind of player he is. Had been all 11 years in Portland. You cannot tell him to quit.

Then his achilles snapped.

“Damn.”

Again, this pairing was given no chance but a glimmer of success in the form of an NBA Cup win, and whether by coaching or personnel, there never felt like a moment where it all harmonized into a true contender. But because of this misfortune, the Trail Blazers’ front office has not only been able to profit by only keeping all of the spoils they have desired from the Damian Lillard trade, but Damian Lillard himself.

I mean again, just look at this freaking chart:

In:	Out:
Jrue Holiday Deni Avdija Toumani Camara Robert Williams III 2028 First Round Swap (MKE) 2029 First Round Pick (BOS) 2029 First Round Pick (MKE) 2030 First Round Swap (MKE)	Anfernee Simons Jusuf Nurkic Nassir Little Keon Johnson

Not quite a king’s ransom, but an absurdly hilarious turn of events and assets nevertheless. And the price is right on the Lillard deal, too, with $42 million owed to Lillard over three years in even chunks. Cronin was able to patch things up with Lillard and then tender this deal because of two elements. The first was deciding to buyout Deandre Ayton’s contract. The second was Jon Horst, general manager for the Bucks, deciding to waive and stretch Lillard’s original contract after the Achilles tear.

So Lillard will now be making $14 million from the Trail Blazers to rehabilitate his leg in Portland, while also receiving $25 million from the Bucks for not being anywhere near the Milwaukee locker room.

To quote Larry Colton in Fast Break, “players are only worth as much as management is stupid enough to pay them.”

The key elements of this deal are that Henderson and Sharpe now have a year to prove that they are players of a focal point caliber and that Damian Lillard gets the people of Portland going. Since LaMarcus Aldridge’s exodus in 2015, Blazermaniacs have filled out the building for the Dame who would be king however the story ended. Chip or bust, dust or glory, Rip City rides and dies with Damian Lillard because he rides and dies with them. He said as much in his return press conference.

So, given that he’s one of the best draft picks and the best free agent signings in franchise history; given that he’s not costing the Trail Blazers that much to return (again, thank you Milwaukee); and given that Portland keeps all the major pieces they wanted from the original blockbuster and subsequent trades, explain to the front office again why they shouldn’t just toss their hands up and say fuck your cap space and fuck your basketball reasons.

The Trail Blazers move.

Perhaps that was not the best choice of words there, but whatever. We’re saving that for later.

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