Dec 21, 2021; New Orleans, Louisiana, USA; Portland Trail Blazers guard Damian Lillard (0) is ejected after communicating with the referee against New Orleans Pelicans during the second half at Smoothie King Center. Mandatory Credit: Stephen Lew-Imagn Images Stephen Lew-Imagn Images

Damian Lillard Reveals Trade Attempt At Former Pelicans Star

Originally posted on New Orleans Pelicans on SI
By Liam Willerup | Last updated Jul 23, 2025 8:07 PM ET

It's been a summer of homecoming in the NBA. The most recent was the Los Angeles Clippers agreeing to bring back franchise legend Chris Paul in what's expected to be the final season of a storied career. Before that, the Portland Trail Blazers agreed to terms on a three-year deal with guard Damian Lillard, who left the franchise via trade in 2023.

Looking at the 2023 trade that saw Lillard go from Portland to the Milwaukee Bucks, it included the Trail Blazers receiving Jrue Holiday from the Bucks, after he served as the team's starting point guard on their 2021 NBA Finals winning team. Holiday joined the Bucks from the New Orleans Pelicans, and Lillard revealed an interesting tidbit on his trade in 2020.

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.
— Sean Highkin (@highkin) July 23, 2025

According to Blazers reporter Sean Highkin, Lillard said that Holiday was a player he was trying to get to Portland in 2020 before he was moved from New Orleans to Milwaukee. Holiday was moved in a four-team deal that sent him to Milwaukee, with other players such as Eric Bledsoe, Steven Adams, and the rights to Yves Missi being included.

Looking at how a potential deal could've gone down, Portland could've sent out CJ McCollum to the Pelicans (earlier than his eventual move in 2023) in addition to young forward Nassir Little and draft capital to acquire Holiday. McCollum and Lillard were a strong scoring backcourt, no doubt, but Holiday's All-NBA level defense would've made for an interesting pairing with Lillard.

5 minutes of clutch Jrue Holiday defense pic.twitter.com/9rKniq4BUM
— Pitless (@pitlessball) June 24, 2025

Holiday and Lillard now have the chance to pair up, despite both players nearing the ends of their respective careers. Lillard could miss all of next season as he recovers from his Achilles injury, but the two should serve as quality mentors for young guards Scoot Henderson and Shaedon Sharpe.

This article first appeared on New Orleans Pelicans on SI and was syndicated with permission.

More must-reads: