Trail Blazers next free agent signing could be one no one saw coming

Milwaukee just opened an unexpected door for Portland.
Denver Nuggets v Portland Trail Blazers
Denver Nuggets v Portland Trail Blazers | Soobum Im/GettyImages

The Portland Trail Blazers continue to be patient in the free agency market, which has left fans frustrated and confused about how their recent moves -- specifically their win-now trade for Jrue Holiday -- tie together with their inactivity. But could it actually be a blessing in disguise?

A shocking new player recently became available with the Milwaukee Bucks waiving and stretching Damian Lillard's remaining $113 million salary, ESPN's Shams Charania reports.

Will Damian Lillard come back to Portland?

Lillard now enters the market as an unrestricted free agent, giving him full control over where he ultimately ends up after Milwaukee. One would guess that Portland would have to be at least in the running, if not towards the top of Lillard's list.

He made it clear that his time in Milwaukee was challenging in terms of being that far away from family. Lillard could rehab in his longtime home and then be a supporting player next season as he gets back into shape.

From the Blazers' standpoint, a reunion makes sense as well, especially given the moves they recently made.

Why a reunion makes sense for the Blazers

There would no longer be a skillset overlap between him and Anfernee Simons following the Celtics trade. In fact, Portland has a Simons void they now need to fill. Given the available options on the dwindling free agency market, Lillard could be their best bet.

One has to wonder how much of a defensive liability Lillard is at 34 years old, coming off a major injury, considering defense was never his strong suit. However, now Portland's roster is much better equipped to cover for him defensively. They have long, athletic wings in Toumani Camara and Deni Avdija, a perimeter ball stopper in Holiday, and an elite rim protector in Donovan Clingan.

The Blazers have all the pieces in place to be a top ten defensive team for the coming years. What they need is more playmaking and, most importantly, shooting. Portland shot just 34.2 percent from three this past season, ranking fifth-worst in the league. That trait will still be there for Lillard when he gets back, as shooting is typically the last thing to go for an aging player.

He also actually fits Portland's timeline in a strange way. Similarly to Holiday, Lillard could be an addition to help the Blazers get back to the playoffs. With his injury, it also wouldn't drastically interfere with Scoot Henderson; Portland could still start him if they want to go that route. This would be a limited window, meaning the backcourt would fully be Henderson's in the coming seasons, giving him more time to develop and become more consistent.

In January of 2024, Lillard said, "I see there being a time where I play for the Trail Blazers," according to Aaron Fentress of The Oregonian.

If Lillard still sees a time when he plays for the Blazers, there's no better opportunity than now.