Damian Lillard’s Return Makes the Trail Blazers a Future Contender

Lillard Comes Home

Lillard returns to Portland to rehab in his home city with his family for a year while he recovers from an Achilles tear he suffered in the 2025 playoffs. If all goes right, he will be back on the court with Portland for the start of the 2026-27 season. 

The roster Lillard returns to is better than any roster the Blazers had during his first 11 years with the team.

He now rounds out a backcourt that features a 21-year-old Scoot Henderson, a 22-year-old Shaedon Sharpe and a fellow 35-year-old Jrue Holiday.

Heartfelt return aside, there is no better destination for Lillard than Portland. The futures of Sharpe and Henderson are still hard to discern — the Blazers need one more year of high-leverage playing time to determine their worth and long-term fits with the team.

Portland can still give both guards their chances at breakout seasons this year. Depending on how this upcoming season goes, the Blazers’ options range from pivoting out of both Henderson and Sharpe’s contract extensions via trades, to re-signing both and bringing Lillard into the fray as a bench piece. 

How the exact rotation would shake out with all four players healthy is wildly uncertain; there has arguably never been a roster with this much budding youth and proven veteran talent at the guard position on a roster at the same time. What Portland certainly does have, though, are options. 

If Holiday and Lillard are still championship-caliber players in 2027, the Blazers can lean in and push for a championship. If either or both have sunk below their primes, or perhaps struggle with injuries, Portland can coax them into reduced bench roles. Trades for Holiday, Henderson and Sharpe are all on the table moving forward (Lillard’s new contract has a no-trade clause).

Big Decisions Ahead

On top of it all, the team has an array of draft capital from 2028-2030 to use if the worst case scenario happens and all four players bottom out, or if they want to make a huge push to go all-in. 

The unique guard rotation joins a very solid wing and frontcourt foundation of Toumani Camara, Deni Avdija, Donovan Clingan , Yang Hansen, with Jerami Grant, Matisse Thybulle, and Robert Williams III providing extended depth.

The biggest questions looming for Portland are what they’re going to do with the extensions of Sharpe and Camara. Portland almost certainly plans to make Camara a staple of their future — for how long and at what price is all that the two parties need to answer. 

With all their options on the table, Portland may decide not to come to an extension agreement this summer with Sharpe. That would push Sharpe into restricted free agency in the 2026 offseason. The most notable restricted free agents of this current offseason have yet to find their new contracts. 

Contending With Goliaths

It’s the most well-known trope at this point that the Western Conference is a gauntlet. The Rockets, Spurs and, most notably, Thunder are three teams that have the generational talents and future draft assets to be contenders for a long time.

Portland needed to make multiple home run moves in a row just to even get their foot in the door with those giants.

Thanks to the humility of Damian Lillard, who turned down multiple mid-level offers from contending teams to return to Portland, the Blazers have now entered legitimate title discussions.