Your exes teaming up to work against you? That’s what it is like for Milwaukee Bucks fans right now after Damian Lillard and Jrue Holiday are now together on the Portland Trailblazers squad.

The two wearing the same jersey in the future seasons is not just a simple work by destiny. Somebody laid down the path long before Lillard got waived by the Bucks.
Dame appeared in front of reporters again after his introductory conference a few days and this time, he got to discuss his future with the team and what would be his dynamics with his future teammates.
One player he said he is looking forward to share the court Holiday who he revealed to be the one who subtly recruited him to Blazers.
“”Damian Lillard said today at his kids camp in Beaverton that as soon as he got waived, Jrue Holiday texted him the 👀 emoji. Also said he was trying to get Jrue to Portland in 2021 when he was traded from New Orleans to Milwaukee,” wrote NBA reporter Sean Highkin.

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Damian Lillard said today at his kids camp in Beaverton that as soon as he got waived, Jrue Holiday texted him the đź‘€ emoji. Also said he was trying to get Jrue to Portland in 2021 when he was traded from New Orleans to Milwaukee.
— Sean Highkin (@highkin) July 23, 2025
News of Holiday’s trade to the Blazers was reported around the last week of June. Lillard was waived a few days after
Damian Lillard’s main reason to return to Portland
Of course, it would be a leap to say that Jrue got Lillard back to Portland. He has more reasons to return there other than that emoji.
Chris Haynes reported early this month that Lillard made a request to get his rehab done in his home in Portland where he has been living with his family since he was drafted by the team in 2012. The reporter said it was what started the ball rolling concerning his eventual waiving by the Bucks.
Another is his bond with the community where he built his legend as their superstar in over a decade.
He was waived and in return, the Bucks got a good deal they were able to stretch his salary to five years instead of two and will only be paid $20 million this season instead of $56 million.

The Bucks then got to sign a young player in Myles Turner who will be paired with Giannis Antetokounmpo on the backcourt.
Lillard said he is excited work with Holiday although their debut on the hardwood will have to wait as he is set to use the whole 2025-26 season to rehab his injured torn Achilles that one can say trigged this development.
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