The Portland Trail Blazers’ decision to reunite with Damian Lillard was a risky one, considering the circumstances.
During the Milwaukee Bucks’ 2025 playoff run, Lillard went down with an Achilles injury, which threatened his status for the entire 2025-2026 NBA season.
The Bucks weren’t willing to wait for Lillard to go through the rehab process, while wondering if he could return to form when he gets back. They have major question marks on their roster that need to be answered as early as possible to keep Giannis Antetokounmpo happy.
Lillard was waived, which opened the opportunity for him to choose his next destination. It wasn’t a surefire contender, but it was an organization that meant a lot to him. In Portland, Lillard has been given the time and the resources he needs to come back as healthy as possible when he is ready.
Lillard Addresses the State of His Recovery
"It's going great," Lillard said on the Road Trippin’ Show. "I think it's just one of those injuries where you’ve got to take your time—you know, it takes what it takes. The first couple of weeks to maybe two or three months is kind of frustrating because you're so limited. But with patience, giving yourself grace, and doing the things necessary to continue progressing, you get to a point where you start to see the light at the end of the tunnel."
Several NBA stars are facing similar circumstances this year. Tyrese Haliburton and Jayson Tatum both suffered Achilles injuries during the 2025 playoffs.
Lillard and Haliburton have confirmed that they would be taking the season off. Tatum, on the other hand, seems to have his sights set on helping the Celtics make a late-season push, as they are on pace to be playoff-bound in early January.
For Lillard, he still doesn’t have any regrets on that front.
The Blazers currently have a shot at postseason play, but they are 10th in the Western Conference with a 14-20 record on the year. Portland is better than expected, but they are still working on getting out of that rebuilding light.
The eventual addition of Lillard should give them a boost, but the 35-year-old guard has to approach every health decision with caution. Rushing back for a potential Play-In run would be too much of a gamble. Waiting to start fresh next season is clearly the safest bet.

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