In September 2023, the Boston Celtics acquired All-Star guard Jrue Holiday from the Portland Trail Blazers as part of a complex trade involving superstar Damian Lillard. Portland had just traded Lillard to the Milwaukee Bucks and then sent Holiday to Boston, receiving Malcolm Brogdon, Robert Williams, a 2024 first-round draft pick, and an unprotected first-round pick in 2029 in return.
Two seasons later, the Celtics traded Holiday back to the Trail Blazers, receiving guard Anfernee Simons in exchange. This move reunited Holiday with the Blazers alongside Lillard, creating a tandem of former stars who had never previously played together in the NBA.
Jrue Holiday’s Role in Damian Lillard’s Return to Portland
The decision for Damian Lillard to re-sign with Portland was reportedly influenced by Jrue Holiday. After the Bucks waived Lillard to create salary cap space for former Indiana Pacers center Myles Turner, Holiday, who knew Lillard personally and understood his connection to Portland, reached out to encourage him.
“As soon as I was waived and obviously [Jrue] knows that I live here and built my home here and stuff,”
Lillard told reporters in Portland,
“He sent me the eyeball emoji. I kind of knew already like — I already knew where I was pivoting to when he sent it but I didn’t want to say nothing too soon, so here we are.”
—Damian Lillard, NBA Superstar
Context of Lillard’s Career and the New Partnership
Lillard spent the first eight seasons of his professional career with the Trail Blazers and owns a home in Portland, which made this return meaningful. Despite being part of the same three-team trade in 2023, Lillard and Holiday never shared the court as teammates until now. The two do have history together on the international stage, having won Olympic gold for Team USA at the 2020 Tokyo Olympics.
Lillard is expected to miss the entire upcoming season as he recovers from a torn Achilles tendon sustained during the playoffs. While there are rumors that Holiday could be traded before Lillard returns, if the pairing remains intact, they will play together in the NBA for the first time after Lillard’s recovery.
Implications of the Trade for the Trail Blazers and Celtics
The trade signals a strategic reshuffling for both teams: the Trail Blazers position themselves with a familiar star in Lillard and a seasoned guard in Holiday, while the Celtics gain an emerging talent in Anfernee Simons. This deal might impact the competitive landscape in the coming seasons as Portland attempts to rebound with its revitalized roster.
The reunion of Lillard and Holiday in Portland introduces a fresh dynamic to the Trail Blazers, blending experience with past team chemistry. Fans and analysts alike will be watching closely to see how this partnership unfolds, especially given Lillard’s recovery timeline and the evolving team strategies in the NBA.