The Milwaukee Bucks have reached a crossroads as they navigate an 18-29 record and a current five-game losing streak while superstar Giannis Antetokounmpo is sidelined with a calf injury amid endless trade rumors and speculation. As the Giannis trade rumors swirl, the Bucks are reportedly finally considering a blockbuster in the days before the trade deadline on Thursday. One surprising team that's trying to get in the mix is the Portland Trail Blazers, with Jake Fischer reporting on a Bleacher Report livestream that former Bucks star Damian Lillard is working “behind the scenes” to try to recruit Giannis to Rip City.

Jrue Holiday, who won a title with Giannis in 2021, is also a member of the Blazers and could be a selling point. Portland controls Milwaukee's draft capital for 2028, 2029, and 2030. The Bucks traded Holiday to the Boston Celtics in 2023 before he got sent to the Blazers this past offseason. Milwaukee let Lillard go in the summer in order to sign Myles Turner.

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However, Fischer noted that there's no indication Giannis has interest in reuniting with Lillard and Holiday in Portland. Fischer also believes it is still more likely than not that Giannis remains a member of the Bucks beyond the Thursday trade deadline. Milwaukee could just be using this week to gauge trade offers for Giannis and then revisit talks in the offseason when more teams could potentially be involved.

The Golden State Warriors, Miami Heat, Minnesota Timberwolves and New York Knicks have been mentioned as the top possible Giannis trade destinations as of right now. While the Blazers are trying to push their way into the mix, they could also potentially act as a facilitator for a multi-team trade even if they can't land the Bucks superstar.