The Portland Trail Blazers need to add to their roster if they hope to contend in a crowded, talented Western Conference in years to come. The most obvious avenue for Portland is the NBA Draft, but they’re well short of San Antonio levels of luck in the annual lottery drawing. One Blazer’s Edge Reader wonders if Portland could make a huge leap via trade, not just for any run-of-the-mill star, but for former NBA MVP and World Champion Giannis Antetokounmpo. Check out the mailbag question here:
Dear Dave,
Could the Blazers be a dark horse candidate for Giannis?
Easy to make salaries match without Portland giving up young talent
2029 Milwaukee pick and the 2028 and 2030 swaps are tremendously valuable to Milwaukee
Blazers could also use other draft capital
Gives new owner a nice shiny toy
Two years left on Giannis’ contract gives Portland options if it doesn’t work
If you squint really hard a team without a proven point guard but length and defenders could be a really good fit for Giannis
Any trade would presumably include [Jerami] Grant and [Anfernee] Simons; Simons’ contract lends itself to a three-way trade that gets both Milwaukee and Portland more of what it wants
Not-So-Swaggy P
Well, it had to come up sometime, didn’t it? And you’re not the only one to ask.
Your reasons are sound as far as they go. And yeah, I’d love Antetokounmpo in a Portland uniform. I’d have serious concerns about three-point shooting still, but the defense, length, and running prowess would make me take the chance without blinking. Get your MVP-level superstar now, worry about the rest later.
I don’t see any way on God’s green earth that it happens, though.
Most of my concerns have to do with Giannis himself. Why is he leaving Milwaukee, the only home he’s known and the team he led to an NBA Title in 2021? Because they have no shot to win again over the next 3-4 years even with him in the fold. But Milwaukee’s roster is far more developed, experienced, and probably talented than Portland’s, especially after trading away the players necessary to get Antetokounmpo. Whomever traded Giannis to Portland clearly didn’t understand the assignment.
I know the dream is pairing Antetokounmpo with Deni Avdija and Toumani Camara to form a fast, physically-dominant defensive unit. Fair enough. That would excite me too. But what else? Championship teams need eight great players (or at least great for their roles) and two solid emergency substitutes. We just named three. That trio better be playing 48 minutes, 82 games, and all through the postseason because the cupboard is pretty bare after.
Let’s be charitable and say the Blazers retain Scoot Henderson and Donovan Clingan to complete the starting five. Athleticism? Check. Defense? Sure. But holy bejeebers who scores in that lineup? Who shoots? Is Clingan as good as Brook Lopez was in Milwaukee a couple years ago? Is Scoot Henderson Jrue Holiday? Our championship designs are already starting to fall apart.
That makes it overwhelmingly likely that Antetokounmpo will simply move on after his contract expires, older and maybe slightly grumpier for the experience. That would happen after the 2026-27 season if he doesn’t pick up his player option year. At that point all the future assets the Blazers traded for him would look stupid.
And that’s IF Milwaukee would go for such a trade in the first place. Yes, they can get their picks back, but people are already speculating that major players like Karl-Anthony Towns could be available for Giannis. I’m not sure Portland’s package matches up to that. I mean, Towns isn’t the answer for the Bucks, but if I’m looking at the choice between him and a Grant-Simons package with some future picks that I already traded away, I’m leaning towards Towns. Especially since I’ve got the albatross of Damian Lillard’s contract still hanging over my head.
Speaking of, there’s one odd permutation of this deal that might work. If the Blazers agreed to take Antetokounmpo AND Lillard with their enormous contract obligations, paying a premium in talent and future picks to do so, the Bucks might at least pause to think. That package could look like Deandre Ayton, Anfernee Simons, Shaedon Sharpe, maybe Scoot Henderson and Robert Williams III if the Blazers can’t make them take Jerami Grant for salary ballast purposes. Plus Portland would trade back the 2030 pick swap and the 2029 first-rounder, maybe throwing in Portland’s own 2027 first-round pick as well.
That offer gets Milwaukee a couple of young players and a few draft assets while freeing them from all serious salary obligations by next summer. It would be a CTRL-ALT-DEL on their roster, which might be what they need. (Assuming they can’t get a better deal for Antetokounmpo on the open market.)
Portland would then suit up Lillard, Camara, Avdija, Antetokounmpo, and Clingan with Grant and Matisse Thybulle in reserve. Plus they still have the 11th pick in this year’s draft for their eighth player.
All this is about as far-fetched as me stepping to the moon right now and opening up a WingStop, but if you want to talk wacked-out theories, there you go. Absent something shocking like that, the Blazers will have to settle for being facilitators in any Antetokounmpo deal and nursing those future pick swaps. The chances of them snagging an MVP candidate in trade are pretty much nil.
So, fellow readers, if you had to take Lillard to get Antetokounmpo and you knew you’d pay a premium in young players and draft capital to do it (no cheap, sweetheart deals!) would you be willing? Share your thoughts in the comment section below.
And thanks for the question! You all can always send yours to blazersub@gmail.com and we’ll try to answer as many as we can!