The Trail Blazers and Damian Lillard are back together after two years apart. He has an unbelievably strong connection to Portland, and with his Achilles injury, Lillard made his way back. Lillard is back in Rip City under coach Chauncey Billups. It is a move that may defy basketball logic, but his commitment is clear.
It Is Not Practical, But Lillard’s Portland Return Feels So Right
Damian Lillard is a legend for the Portland Trail Blazers. Throughout his first stint from 2012 to 2023, he was the model Trail Blazer. He always stuck with the team through thick and thin, but it came to a tipping point in 2023. Despite his desire to stay, the situation was too dire, so he requested a trade.
Unfortunately, the grass was not as green as expected with the Milwaukee Bucks. He and Giannis Antetokounmpo never had the chemistry required for a superstar partnership. They lost in the first round of the Playoffs twice, including a second run when he ruptured his Achilles tendon.
Due to that injury, the Bucks chose to buy out his contract, clearing the way for Portland. It might not be the most logical move, but it is meaningful for fans who never wanted him to leave. Now, Lillard is back on a three-year deal worth $42 million.
Some Moves Mean More Than Basketball
Lillard won’t be playing in the 2025-26 season due to his rehabilitation from the Achilles injury. That means Scoot Henderson and Jrue Holiday will take care of the point guard position. This is an opportunity for Henderson to establish himself as the long-term starting point guard. Chauncey Billups will have plenty of options in the guard position when 2026 comes around.
RipCityyyyyyyyyyyyyyyyy!!!!!!!!! @trailblazers pic.twitter.com/x3jnZr1s0G
— Damian Lillard (@Dame_Lillard) July 17, 2025
With this decision, Henderson has one season to prove that he is the real deal. Billups believes in his development, but he needs to get results. Thankfully, it seems the Blazers aren’t giving up on Henderson, considering he has barely scratched the surface of his potential.
This is a more sentimental move for the organization and the player. Lillard is arguably the organization’s greatest player, and the fans adore him. Since he will not be playing for a while, he will stay at home in Portland. Thankfully for him and the organization, both parties were willing to reconcile.
The Basketball Implications of the Lillard Return
While it is a fantastic time for Blazers fans, there should be some time to reflect. This reunion does not make the most sense in the basketball context. The Blazers are building the team for the long-term future, but this return could stunt the young players’ development.
The player facing the most pressure will be Henderson. He has a season to prove that he belongs in Portland as the team’s star point guard. Lillard will return as a star in the 2026-27 season, but they could coexist as long as Henderson proves himself. That was the initial plan back in 2023, but Lillard requested the trade before they could share the court.
DAME x SCOOT: Scoot Henderson was touted as the next Damian Lillard for the Portland Trail Blazers when they selected him No. 3 in 2023 NBA Draft.
Now, two years later, Lillard returns to Portland & will have a massive impact on Henderson, being a mentor on & off the court for… pic.twitter.com/k852s0lfyK
— Courtside Buzz (@CourtsideBuzzX) July 18, 2025
Portland already has the issue with balancing Holiday and Henderson. Adding Lillard to the mix might be a bigger issue the Blazers should consider. It will be up to general manager Joe Cronin and Billups to make the important decisions.
In the meantime, Lillard and Holiday will mentor Henderson. That is huge for the young guard, as he can learn from two experienced players. This is a net positive for Portland, as Henderson always values learning from his teammates and coaches. As long as the Blazers support the 21-year-old, he could break out as a star equipped with veteran knowledge.
With an ever-developing Shaedon Sharpe and Henderson learning from veterans, the future is bright. It will be up to Billups to strike the right balance in his rotation. However, if he develops the team well, it should be an easier decision in 2026.
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