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The Milwaukee Bucks have been backed into a corner when it comes to the inevitable Giannis Antetokounmpo trade all season. Had they acted sooner, they likely would have received a historic haul for their two-time MVP. Asset-rich teams like the Spurs and Rockets might have been interested last summer. They’ve since moved on, and that has left the Bucks to sift through lesser offers.
Trading Antetokounmpo for, say, Karl-Anthony Towns and Mikal Bridges would do little for Milwaukee’s long-term outlook. Golden State’s draft picks are potentially valuable, but ultimately a mystery box. Kel’El Ware is a promising young big. You’d expect someone with a clearer path to stardom to be the centerpiece of an Antetokounmpo package. But what could the Bucks do? Antetokounmpo is set for 2027 free agency. They had no leverage. They could trade him for 50 cents on the dollar or let him leave for nothing.
The Portland Trail Blazers have entered the chat.
On Saturday, Marc Stein and Jake Fischer reported that Portland “has also expressed its own interest to the Bucks that it would like to acquire Antetokounmpo … even as the Blazers realistically understand that it would be an extreme long shot to convince Giannis to sign a contract extension that keeps him in the Pacific Northwest.”
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Now, there are quite a few caveats here. For this to matter for the Bucks, Portland either needs to be able to convince Antetokounmpo to agree to a long-term extension or be willing to trade for Antetokounmpo without those assurances. At this stage, neither seems especially likely. If either of those conditions is met, however, it changes everything for the Bucks and the other teams hunting for Antetokounmpo. If the Blazers are really willing to do this, that’s checkmate. They win the Giannis sweepstakes, and the Bucks walk away with a better package than any of the other parties known to be interested can offer. So let’s get into why Portland is such a critical variable in these trade talks, what a deal could look like, and what obstacles need to be cleared in order to make this happen.
So… why are the Blazers so important?
Most of the time, the most valuable thing a team gets when it trades away a superstar is extra lottery balls. Consider the Chris Paul trade in New Orleans. The then-Hornets technically got a package centered around Eric Gordon and Al Farouq-Aminu… but practically speaking, the trade netted them Anthony Davis because it made them bad enough to tank for him in the first place. Houston trading James Harden set the Rockets up to draft Amen Thompson and Jabari Smith. The Spurs got three first-round picks for Dejounte Murray, but it also kickstarted the tank that led to Victor Wembanyama. I could go on and on. It was incidental, but remember, even the Mavericks last year likely wouldn’t have gotten Cooper Flagg without the Luka Dončić trade. That wasn’t the plan, but with Dončić, Dallas probably makes the playoffs and doesn’t have the 1.8% chance it needed to secure Flagg.
This is problematic for Milwaukee because the Bucks no longer have their own picks. Between the Jrue Holiday and Damian Lillard blockbusters in 2020 and 2023, the Bucks owe control over their first-round picks through 2030 to other teams. Their 2026 pick technically belongs to Atlanta, but that’s not the end of the world. Milwaukee will either have its own pick or it will swap with New Orleans, whichever pick is lower. As the Pelicans and Bucks are both bad, the Bucks will land somewhere in the lottery either way. Their 2027 pick is probably unobtainable. It’s tied to a separate trade with the Hawks, and for New Orleans to give the Bucks control over it again, they would either have to make a side deal with Atlanta or they would have to surrender control of their own 2027 pick. That feels unlikely considering all of the bad press they got for giving away their 2026 pick.
But 2028 through 2030? Those all belong to Portland through the Lillard trade. There are some strings attached to those picks through follow-up Portland trades we’ll cover shortly, but the Blazers broadly have the ability to give the Bucks control of their picks back in all three seasons. There had been some assumption that teams might try to use Portland as a facilitator in a Giannis trade for exactly this reason, but if the Blazers want him themselves, they can jump the line and make the best offer rather easily.
Look at it this way. One of the hypothetical trade packages widely regarded as among the best Milwaukee could get for Antetokounmpo would be a collection of four first-round picks and a first-round swap from Golden State. Warriors’ picks, especially deep in the future, do hold a fair bit of value. Stephen Curry is about to turn 38, after all. But those picks are a bit of a mystery box. The Bucks don’t know what the Warriors will look like in 2032, and they have no control over that. You know what the Bucks can control? How bad they are. They can essentially guarantee themselves high draft picks by stripping their roster of valuable players in years in which they actually have control over their own first-rounders. Trading for Warriors picks, or Heat picks, or whoever else’s picks, doesn’t come with that layer of security. The Brooklyn Nets just did this in the summer of 2024, trading control over a number of valuable future draft picks from the Suns and Mavericks to the Rockets to regain control of their own picks in 2025 and 2026.
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This is even a model Portland could adopt as a hedge. Houston had three future Nets picks remaining when they made that trade. They gave the Nets two of them and kept the third, in 2027, betting that Brooklyn’s tank in 2025 and 2026 would make the Nets worse in 2027 and thus give them a higher pick. Portland has more than enough young talent and draft capital from other sources (including its own) to potentially send the Bucks, say, control over their 2028 and 2029 picks, along with other assets for Giannis while keeping the 2030 pick. The exact structure of the trade would of course be subject to negotiation with the Bucks, but overall, this is what Portland’s involvement is a best-case scenario for Milwaukee. They gave the Blazers their ability to traditionally rebuild in the Lillard trade. Now they could use Giannis to get it back.
So what would a trade look like?
First things first: We have to address matching salary. This seems pretty straightforward. We can assume Jerami Grant and his $32.4 million contract would be in the deal. It would make sense for Scoot Henderson, the No. 2 overall pick in 2023, to be in the trade as well. He hasn’t played this season due to injury, and if Antetokounmpo got to Portland, he’d just never have the ball enough to develop properly. Milwaukee might actually be a perfect situation for him. He’d be surrounded by shooting, including a shooting center in Myles Turner, and he’d have little competition for touches and shots. Maybe the Bucks could turn him into the star Portland hoped it was getting when it picked him second.
From there, again, it’s a matter of negotiation. Portland would probably make likely first-time All-Star Deni Avdija off limits. Aside from being their best player, he’s on a preposterously cheap contract that would be critical in building a deep team around Antetokounmpo. There’s still plenty of other interesting young talent here for Milwaukee to consider. The Bucks are depleted on the wings. Maybe they’d want 25-year-old reigning All-Defense pick Toumani Camara. Maybe they’d want Donovan Clingan, an imposing defensive center. Maybe they’d want a lottery ticket on No. 16 overall pick Yang Hansen. Maybe they’d like Shaedon Sharpe‘s scoring punch. Some combination of these young players, Milwaukee’s own picks and other draft assets from the Blazers would make up this package.
However, we have to talk about those Milwaukee picks that Portland controls. The 2030 pick is simple. Portland just has swap rights. Therefore, the Blazers could simply renounce those rights. Easy enough. The 2029 pick is a bit more complicated. Portland has control over three picks: its own, Milwaukee’s and Boston’s. However, Washington is owed the second-most favorable of those three picks from the Avdija trade. Again… no problem. Portland can just agree to give Milwaukee the best of the three. Milwaukee could tank on its own, and if Portland or Boston happens to be worse than them organically, that’s just a pleasant surprise for the Bucks.
But 2028? Yeah, 2028 is a mess. There are two major reasons as to why.
- Milwaukee traded Portland’s first-round swap rights in 2028 as part of the Lillard trade. However, it proceeded to trade secondary swap rights on that same first-round pick to Washington at last year’s deadline in the Kyle Kuzma trade. This matters because it means Portland cannot simply renounce the swap rights it has with Milwaukee, because then Washington would just get unfettered access to Milwaukee’s pick.
- Portland currently owes Chicago a lottery-protected 2026 first-round pick. It remains lottery protected through 2028. This means that if the Blazers miss the playoffs in 2026 and 2027, but make them in 2028, Portland will not have its own pick to swap with Milwaukee in 2028, once again setting Washington up for unfettered Bucks swap rights in 2028.
So, can the Blazers clean this mess up? Yes, it would just be a complicated, multi-step process. The first step would be settling its business with Chicago to ensure that it has control over its own 2028 pick. The easiest way to do this would be to call the Bulls and offer to remove the protections on the pick this season. That would mean Chicago would get Portland’s pick in 2026, no matter what, setting Portland up to keep its pick in 2028. The alternative would be to offer the Bulls some other draft compensation to get the 2026 pick back. Portland happens to have an unprotected 2028 pick from the Magic from a draft-night trade last year. Would the Bulls rather have that pick than this protected Blazers pick? If so, we’re in business.
Now, once Portland has its own pick back, it would have to trade it to Milwaukee. This would give the Bucks both their own pick and Portland’s, allowing them to keep the better one while still honoring Washington’s right to swap for the lesser one. Essentially, this means that if the Blazers and Bucks could successfully bribe the Bulls, there’s a path to Milwaukee getting its 2028 pick back. It would just mean Portland losing control over its own. But hey, they’d be getting Giannis Antetokounmpo. They’d surely assume their own 2028 pick wouldn’t be that valuable.
Would Giannis really re-sign with the Blazers?
Everything we’ve covered means nothing if the Blazers don’t believe they can secure an extension with Antetokounmpo. If Antetokounmpo tells them directly that he’s in, great, we can get the ball rolling. If Antetokounmpo directly tells them that he absolutely would not re-sign under any circumstance, Portland’s out. They’re not trading the farm only to watch Giannis walk into the Lakers‘ open cap space in the summer of 2027.
Where this gets more interesting is if Antetokounmpo is non-committal in either direction. If he says he’d keep an open mind but wouldn’t agree to an extension right away. Technically, Antetokounmpo is not eligible for an extension until October, three years after he signed his last one. This is a vital detail, though, because that window falls in the offseason. If Antetokounmpo is traded before the deadline, he’s still eligible to sign a four-year, roughly $275 million extension before next season starts.
However, if this drags into the offseason, he’d lose that eligibility. His max extension goes beyond the league’s extend-and-trade guidelines, meaning he’d have to wait six months after the trade to get the most possible money. Say he’s traded on July 1. That means he would have to wait until Jan. 1, 2027, to sign that extension. Antetokounmpo has dealt with calf injuries all year. He might not want to risk going into next season without having that extension signed.
So his motivation would be to get traded by Thursday’s deadline. However, Milwaukee’s preference would probably be to execute a trade over the summer. At that point, the pool of possible suitors for Giannis expands. Maybe a team like the Spurs, Rockets or Pistons has a disappointing postseason and reconsiders pursuing him. Maybe a team’s financial circumstances change in such a way that enables a pursuit. Orlando checks this box. The Magic can’t seriously pursue Giannis right now, but once Paolo Banchero‘s rookie extension kicks in over the summer, it gets much easier for them to offer their former No. 1 overall pick for Antetokounmpo. If nothing else, teams like the Knicks, Heat, Warriors and Timberwolves would all gain access to their 2033 first-round pick just by virtue of the league year turning over.
So here’s the scenario in which Antetokounmpo might become more amenable to Portland. We get closer to the deadline. The Knicks, Heat, Wolves, Warriors and whoever else make underwhelming offers. The Bucks approach Antetokounmpo and say, “Look, none of these other teams have made an offer we’re willing to accept right now. If you want to go to one of them, you’re going to have to wait until the summer. If you absolutely have to get traded right now, the only offer we’re prepared to accept today is Portland’s.”
In that scenario, Antetokounmpo would have to decide whether getting traded now, and therefore having extension eligibility in the offseason, would be worth going to a destination he might not have originally considered one of his preferences. He might still elect to say “wait until the summer.” But maybe he decides at that point that Portland makes sense, and even if he couldn’t technically put pen to paper on an extension until October, if he gave the Blazers his word that he would re-sign, they’d likely accept that as enough. This would, in essence, be a compromise between Giannis and the Bucks. Milwaukee agrees to trade him without scoping out the market more fully over the summer. Antetokounmpo goes to a team he might not have originally chosen in order to get traded faster.
In basketball terms, at least, the Blazers actually would make some sense. Portland, after all, employs his former championship teammate, Jrue Holiday, as well as his more recent Milwaukee teammate, Damian Lillard. If Antetokounmpo is still close with them and interested in a reunion, as some reporting has suggested, Portland can offer it. The Blazers also have more roster optionality than most of the teams in the hunt here. Those Milwaukee picks should allow the Blazers to make a compelling offer without giving up everything they have, giving them room to make further roster adjustments afterward to suit Antetokounmpo’s needs or desires.
Say Portland made Avdija off-limits in the Antetokounmpo trade. If there was a specific teammate Antetokounmpo wanted that was somewhere else in the league, Portland could offer Avdija to get that player. There might even be permutations of the Giannis trade itself that allow the Blazers to bring back Myles Turner as well, an ideal center fit for Giannis, thanks to his shooting, by sending back some more draft value and a few of their expiring contracts.
The market is a concern here. There has been reporting indicating that Antetokounmpo would prefer to live in a warm-weather city. Portland is also about as far away from his offseason home in Athens as any NBA market. If that’s a consideration, well, there’s little Portland can do about it. Moving from the Eastern to the Western Conference would obviously make it harder for him to contend as well. Without knowing what Portland’s roster would ultimately look like, it’s hard to say where it would fall in the Western Conference hierarchy. Odds are, it would be behind the defending champion Thunder at least. Especially since Lillard almost certainly won’t play this season, and we have no idea what he’ll look like next year coming off a torn Achilles.
In other words, it’s probably unlikely that Antetokounmpo is willing to commit to a future in Portland. If he’s not, well, I’ve wasted 3,000 words worth of your time. But Portland registering any degree of interest does matter here. Even if that doesn’t necessarily mean he’s going to the Blazers, it does give the Bucks a shred of leverage. It means there is at least one team, however unlikely it might seem, that is both capable of making the Bucks an appropriate offer and potentially willing to do so. That puts pressure on the more aggressive, but asset-poorer suitors to step up their own offers as the deadline approaches.
And hey, it’s not impossible that he’d be willing to play in Portland. There’s been some reporting stating his interest in Minnesota, a similarly small and cold market. If Holiday and Lillard recruit him, if they convince him they have a path to putting a contender around him, or even if he’s just eager enough to get that next contract from a team besides Milwaukee to force the issue now, there is a path, however narrow, to Giannis wearing red and black this season.