The Giannis Antetokounmpo trade conversation has dominated this NBA season, especially as the Milwaukee Bucks continue to flounder, but now, things are changing. This isn’t just about the usual big-market suspects like the New York Knicks circling the Greek forward, but also about specific situations that might turn out to be the real answer in a drawn-out potential trade. Bobby Marks of ESPN discussed one of those destinations.

“Chicago has eight players on expiring contracts,” Marks explained, standing in front of a big screen with both teams’ cap situation and draft picks. “You have players like Josh Giddey, Nikola Vucevic, who’s on an expiring, Kevin Huerter here.”

The NBA reporter then pointed to a simple but risky game plan.

“They’ve got draft picks, they’ve got their own four in the next seven years,” Marks said. “They also have a pick from Portland here. I think if you’re a team like Chicago or any of these teams that we have not heard about that have all these assets, it’s kind of like in-house recruiting.”

The plan: Trade for Antetokounmpo, then convince him to stay after he arrives. The projected salary cap next year is $166 million, which would give the Bulls about $84 million in cap space, more than enough to sign the Greek Freak to a maximum deal.

This gives the Bulls massive flexibility while also retaining valuable young talent like Josh Giddey, who’s under contract for a mid-tier long-term deal.

Marks explained that he himself had done something similar when he was in a front office role in 2010:

“We did it when I was in New Jersey with Deron Williams,” Marks said. “We traded for him. There was no assurance that he could stay. You make some trades, high-risk trades. It cost you certainly down the road here.”

The Bulls can afford to make a gamble for Antetokounmpo, but they’re not the only ones. While the Golden State Warriors have repeatedly been deemed the best suitor because they have a variety of future picks to trade, there’s another dark horse that’s rumored to be running alongside them.

Why the Portland Trail Blazers are willing to gamble on a long shot for Giannis Antetokounmpo

The Portland Trail Blazers being involved in the sweepstakes for Giannis Antetokounmpo feels absurd, but everything begins to make sense once you follow the relationships.

“The Blazers themselves are trying to get into the mix to bring Giannis Antetokounmpo to Portland to play alongside his former teammate Damian Lillard,” NBA insider Jake Fischer reported on a Bleacher Report livestream. “[Lillard] has been someone who’s been trying to make this happen behind the scenes. His former teammate Jrue Holiday is, of course, still in Portland.”This potential reunion isn’t just about the fit on the court (Lillard is out for the season), but selling Antetokounmpo on a vision of trust and comfort that he knows and appreciates.

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However, the Blazers also have assets to make things work. They have flexibility thanks to their young players. The team can also act as a facilitator in a larger deal or be an aggressive bidder. Crucially, they hold the Bucks‘ first-round picks and swaps from 2028 to 2030, giving Milwaukee extra incentive to negotiate with them.

The Blazers also have a salary-matching alternative with contracts such as Jerami Grant’s $32 million deal and other mid-tier salaries like Robert Williams III’s $13 million.

The theme of the Antetokounmpo trade rush is risk. For small-market teams, there’s no guarantee of retention. The front offices in Chicago and Portland must weigh whether the potential reward is worth gutting their timeline.