Dame Comes Home – Four Futures That Could Define the Trail Blazers’ Next Era

In a storybook reunion that no one saw coming, Damian Lillard is back in Portland just two years after a heartbreaking departure to Milwaukee. 

Blazers fans had hoped that Lillard would return someday, but that day arrived a lot sooner than anyone could have hoped for. 

Bringing Lillard back is essentially a can’t lose decision for Portland, even in the worst-case scenario. Four outcomes can result from Dame’s homecoming. 

Let’s break them down.

1. Portland good, Dame good: This is the best-case scenario, and one in which everything goes Joe Cronin’s way. I’ve criticized Cronin for never picking a clear path. Now every path he picked could converge in a legendary Trail Blazers team. Think about this way. In return for Damian Lillard, Anfernee Simmons, and Jusef Nurkic, the Blazers received: Jrue Holliday, Toumani Camara, Deni Avdija, a 2028 unprotected pick swap with the Bucks, a 2029 unprotected draft first round pick, a 2030 unprotected pick swap, and … Damian Lillard. That is one insane piece of work that he has pulled off. The Trail Blazers now have the veterans in place in Lillard and Holliday, a blossoming young team that has a year to figure things out before Lillard even steps foot on the court again. If Lillard returns to even 70 or 80 percent of his former self in the 2026-27 season, and the rest of the pieces turn out how the Trail Blazers hope, Portland is going to be terrifying to contend with. Will Dame start? How does he mesh with the new blood that has taken root since he’s been gone? None of it matters for this year. They have a year to figure out how to make everything work, and then they may be the best team in the west to pull off a similar trick to Oklahoma City – making deep runs to the playoffs while still possessing a pile of strong draft assets. And like Oklahoma City, it could very well end up seeing the Trail Blazers host their first championship banner in 50 years. 
2. Portland good, Dame bad: This scenario isn’t as great. Perhaps Lillard returns as a shadow of his former self or reinjures himself during rehab. Either way, the Trail Blazers essentially continue the same course they set before his return, just without Lillard making a significant impact. Lillard sticks around as a cheerleader for the young guys in an environment where he clearly feels comfortable, and the Trail Blazers thrive even without him seeing significant time on the court. This would still be a pretty big win for the Trail Blazers. Lillard’s contract is not prohibitive, and it would roll off the books at the same time as Holliday, allowing the veterans to depart as the next generation assumes the mantle of leadership. 
3. Portland bad, Dame good: This one would certainly be bittersweet for Trail Blazers fans, considering they sat through plenty of years like this at the end of Lillard’s previous tenure in Portland. The scenario assumes the Blazers don’t reach their desired destination this season and then continue to struggle in 2026. Lillard received a full no-trade clause as part of his two-year deal, which includes a third-year player option to return to Portland. Still, one would figure that if the Trail Blazers are stuck in the basement while he continues to play at a high level, he would waive it to go to a contender of his choice in time for a playoff run next season. While the chosen team may not have to surrender much in terms of assets, considering they would be negotiating from an exclusive position, anything the Trail Blazers received back would essentially be icing on the cake of what they received from trading Lillard the first time around. 
4. Dame bad, Portland bad: This would be the worst of all worlds. The Trail Blazers don’t reach their promise, and Lillard is either hurt or ineffective. In this scenario, none of the bets that Joe Cronin made on the team pay off. But he’s also probably not around to watch the team spiral too far. With new ownership on board, the team is quick to jettison the old regime, with Cronin and Billups shown the door as the 2026-27 season spirals. Lillard gets a farewell tour as the season wraps up, and with so much change swirling around the franchise, doesn’t opt in for the 27-28 season. As Lillard and other veterans come off the books, the team once again embarks on a rebuild. Even in this worst-case scenario, the timing of the contracts the team handed out allows them a fresh start with minimal long-term anchors on the team as they reboot things again.

No matter which scenario lies ahead for the Trail Blazers, the next few years are going to be entertaining to watch, and with the franchise icon back in the fold, they may have the makings of something incredible.