The latest Jrue Holiday buyout chatter appears to be nothing more than noise, and that’s probably a relief for Bucks fans who don’t need another painful reminder of what Milwaukee lost.
Marc Stein reported in his latest piece for The Stein Line that the idea of Holiday being bought out by the Trail Blazers is “erroneous.” He wrote that it has become “a popular online pastime” to float the notion, especially with talk of a possible route back to Philadelphia, but league sources say Portland is not preparing to send him to the open market.
The message from Portland has apparently been clear for a while. According to Stein, the team has “been messaging for some time” that it intends to keep Holiday.
That should take some heat off Milwaukee’s already bruised feelings about the trade that sent Holiday out in 2023 as part of the Damian Lillard deal. Portland later moved him to Boston, where he played a key role in the Celtics’ 2024 title run. For Bucks fans, that sequence has already been annoying enough without adding a fresh round of reunion speculation.
A return to Philadelphia would have made the rumor mill even louder. Holiday spent the first four seasons of his career with the Sixers, and the idea of him winding up there again had been gaining traction online. But that door appears shut for now.
Holiday remains under contract for at least one more season, and he has a $37.2 million player option for 2027-28 that he will, in all likelihood, pick up. That decision comes next offseason. For now, Portland seems intent on keeping him in the fold as it chases its own title hopes, with Lillard back in the mix.
At 36, Holiday still has plenty of value, which is why a buyout never made much sense in the first place. A trade deadline move could always become part of the conversation later, depending on how the first half of the season unfolds, but that’s a long way from anything concrete.
For now, the Sixers can cool off on the Holiday dream, and Milwaukee can be spared another round of what-if grief.
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For Milwaukee, the move is a small reminder of how quickly the back end of a roster can turn over. Jackson was part of the Bucks' recent development pipeline, the kind of young guard a team hopes can grow into a useful rotation piece, and his next stop now puts him in a familiar late-summer fight for jobs and minutes. Whether he finds one in Toronto or lands in the G League system, the Bucks are left to weigh what his departure says about their own depth and the players still trying to break through. [Read more 🡒]
