It’s crazy how NBA works as Milwaukee Bucks fans will now see the two points guards they swapped with each other – Damian Lillard and Jrue Holiday – working together now for the Portland Trailblazers.

It was Jrue who was first sent to the Western conference team after two years and one championship with the Boston Celtics. Then the injured Lillard was waived by the Bucks and then he agreed to return to his former team where he already built his legend.
The pair is being seen as opposites and juggernaut at what they do. Holiday on the defense, Lillard on the offense.
Dame said Holiday’s addition to Portland is one thing he is looking forward to.
“That’s one of the things that I’m extremely excited about,” he told reporters on Wednesday.
Of course, Lillard can only hope that the two-time All-Star will still be with the team by the start of next season because of his situation.

He signed a three-year deal with his former team worth $42 million but the team has accepted that he will not be able to play for one whole season and that he will focus on his rehab.
Damian Lillard on relationship with Jrue Holiday
Dame and Jrue went opposite ways when they got traded in 2023, playing for main rivals in the East. They remained connected.
The Blazers great said Holiday allowed him to rent his home in Milwaukee. There’s one problem he is jokingly complaining though. The Wi-fi connection.
“When I lived in Milwaukee, I rented his house for two years so we talked a lot,” Lillard said.
“Like, I was complaining to him about the wifi. There’s a clip online of like I shake his hand, we played them in Boston, we had an interaction and people we’re like what? And we were literally talking about his wifi at his house.”

That video he is talking about is seen below.
What’re they talking about…? 👀
Wrong answers only pic.twitter.com/W0OqO388Au
— Celtics on NBC Sports Boston (@NBCSCeltics) November 22, 2023
Lillard himself confirmed this.
Yes, we were talking about WiFi issues 🤣 @Jrue_Holiday11 https://t.co/DxzVlK4Tyf
— Damian Lillard (@Dame_Lillard) July 24, 2025
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