The Boston Celtics lost their chance at getting Giannis Antetokounmpo, and now they are dealing with the Jaylen Brown trade rumors. Among the teams interested in Brown is the Portland Trail Blazers, who actually have a better package than most think, but here's a good question.
Why didn't the Trail Blazers become the third team in a Giannis-Brown trade?
Portland has the draft assets that would appeal to a team trading its star, as they have pick swaps with the Bucks in 2028 and 2030. Know who that really could have appealed to? The Bucks themselves.
A blockbuster trade where Giannis got sent to Boston, Brown got sent to Portland, and those pick swaps were sent back to Milwaukee would have given them a clean slate they desperately needed following the Giannis fallout.
Given what Portland is reportedly willing to offer, it's also fair to suggest that they would have had the young players to also help the Bucks kickstart their rebuild in full. It's not like their young players are all game-changers, but compared to what the Heat gave the Bucks, the comparison is, at the very least, well, comparable.
What’s been expressed to me - as it pertains to a Jaylen Brown deal - I don’t expect Deni/Clingan/Camara would be in those talks.
— Danny Marang (@DannyMarang) June 27, 2026
Grant/Sharpe/Henderson and any/all draft capital - that’s the pot I believe they’re working with.
This seemed like a pretty straightforward make for Milwaukee, but instead, they settled on the Heat's pu-pu platter because, in theory, they believed there was a stronger probability that Giannis in South Beach would fail than he would in Boston.
They may come to regret that.
It supports the theory that the Bucks simply didn't want Giannis on the Celtics
Perhaps Milwaukee believed that they would get better assets from the Heat than they would if they got their own back in a deal. That's very possible, but it's also possible that they straight-up just didn't want Giannis in Boston because of how tremendously it would have potentially worked out for them in the end.
The Celtics thrived in a down season where Jayson Tatum was out for most of the season while recovering from an Achilles tear. With him potentially being healthier, combined with a healthier Giannis, Boston could have reached a level they hadn't seen since they ruled the league in the 60s.
Maybe Milwaukee thought that vying to get their draft picks back wasn't enough to justify creating a new dynasty in Boston. Instead, they run the risk of giving up golden assets to Portland and New Orleans over the next half-decade. Shouldn't their primary mindset be to create the best future you can for yourself, rather than trying to prevent the best future for an opponent?
If they wind up being one of the worst teams in the NBA when it's all said and done from this, and have absolutely nothing to look forward to because of it, they will only have themselves to blame, but at least the Brooklyn Nets will know how they feel...
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