Jrue Holiday and Damian Lillard's careers have become intertwined. They got traded for each other in a move the Milwaukee Bucks hoped would help bring the franchise its third championship.
Their primary motive was getting Giannis Antetokounmpo to sign an extension to stay in Milwaukee. He did so. However, on the heels of their home run swing, the Portland Trail Blazers rerouted Holiday to the Boston Celtics. He became an integral figure in the latter's capturing its record 18th NBA title.
Now, Lillard and Holiday will partner on the Trail Blazers. The former recently signed a multi-year deal to return to the franchise where he starred for 11 years. The latter arrived via a trade with the Celtics that sent Anfernee Simons and second-round draft capital to Boston.
Lillard, whose Achilles tear could prevent him from ever sharing the backcourt with a teammate he will likely join in the Basketball Hall of Fame one day, recently met with the local media in Portland. During that interaction, he offered another layer of the connection between him and Holiday.
"When I lived in Milwaukee, I rented his house for two years, so we talked a lot," shared Lillard. "Like, I was complaining to him about the wifi. There's a clip online [where] I shake his hand; we played them in Boston, we had an interaction, and people were like 'What?' And we were literally talking about his wifi at his house."
Now that they will be teaming together, Holiday reached out to Lillard to learn more about the organization he is joining and the city that will become his new NBA home.
Damian Lillard on his relationship with Jrue Holiday 😂😂
— Brenna Greene (@BrennaGreene_) July 23, 2025
"When I lived in Milwaukee, I rented his house for two years so we talked a lot. 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… pic.twitter.com/42mpBv5tzr
"I love Portland," relayed Lillard. "I live in Portland. My family's in Portland. It's a place [where] when people come here to play, it's probably raining, they're here for a night, [and] it's gray skies. You don't really see much, but it's -- I mean, I'm from California, and I've been living here for the last 13 years.
"So, I think once you get here and you get on the ground, you learn to like it, or love it in my case. That was kind of what I shared with him."
Celtics pained by Jrue Holiday trade
Boston didn't want to part with Holiday. The Celtics' president of basketball operations, Brad Stevens, loved him from afar before finally being able to bring him on board entering the 2023-24 campaign.
Holiday was a selfless Swiss army knife who excelled at whatever role the team required of him. He also made an impact in the community.
Unfortunately, Jayson Tatum's Achilles tear and the consequences of staying over the second apron for consecutive seasons meant changes were coming this offseason.
With the franchise needing to prioritize regaining flexibility, their hand was forced. While they wished it wasn't the case, the prudent move was trading Holiday, who is on the books for $32.4 million for the 2025-26 campaign.
The Celtics are still over the second apron, but as an executive told Keith Smith of Spotrac, that will change.
"Still figuring it all out," said the team exec of Boston's roster reshuffling. "We're still above the second apron. We won't finish there. It sucked to trade Jrue [Holiday] and KP [Kristaps Porzingis], because we loved those guys and they loved Boston," he noted.
"But it was being brutally honest that we aren't the same level of team without Jayson [Tatum]. We'll be good. We'll be a playoff team, but…you know. It'll come for every team that lands where we did. You can't be over the second apron and not a title contender. It's just poor management for both the short- and long-term. The frozen pick and pick dropping stuff is real."
The Celtics can get back below the second apron by waiving JD Davison's non-guaranteed contract. However, one would anticipate that more moves are coming.
The organization can reset the repeater tax by getting under the luxury tax threshold in consecutive seasons. They're $20.3 million over that line, per Spotrac.
Perhaps that proves too difficult to accomplish. However, Boston still might shed enough payroll to get below the first apron. The franchise is over that marker by $12.2 million.
So, while dodging the second apron won't be a challenge, the Celtics will likely try to create more flexibility during this unwelcomed opportunity to reset itself.