The Portland Trail Blazers head into the new NBA season with a mix of excitement and uncertainty as Damian Lillard returns to Portland. The veteran guard is back with the team but is still working his way back from an Achilles injury, raising questions about how much he can contribute right away.

Lillard has been open about what he believes could have been during his first stint with Portland. Reflecting on his early years alongside LaMarcus Aldridge, the Trail Blazers star said their group had all the pieces to compete for a championship and truly believes they would have broken through if not for injuries and inexperience.

“I felt like, in the next one or two years, we would have won it,” Lillard said on his YouTube channel. We were one of the best teams in my second year, just inexperienced. We were one of the best teams for a long time. In my third year, we just had a lot of injuries, like major injuries. I feel like that fourth year would have been a good year.”

Lillard’s first era with Portland is often remembered for early playoff exits and frustrating stretches of mediocrity. Whether paired with CJ McCollum or Carmelo Anthony, those Trail Blazers rarely advanced past the first round of the postseason. Still, there was a window early in Lillard’s career when it felt like Portland had a real chance to chase an NBA title.

Lillard’s path with the Blazers

Aldridge and Lillard formed one of the most promising duos in the league at the time, and their complementary skill sets gave the Trail Blazers a balanced, dangerous lineup. Unfortunately, injuries and timing kept them from fully realizing that potential.

In Lillard’s rookie season, Portland finished 11th in the West with a 33-49 record. It wasn’t until the 2013-14 campaign that the Trail Blazers broke through, finishing fifth in the conference at 54-28 and sending Lillard to his first All-Star appearance. The following season, Portland improved again, posting a 51-31 record and earning the No. 4 seed before falling to the Memphis Grizzlies in the first round.

Lillard remains convinced — as do many fans who watched that team closely — that if the core had stayed healthy and given time to grow, Portland could have made history. The combination of youth, patience, and a little bit of luck might have been enough to deliver a NBA championship run.

Lillard’s return to Portland

Now back in Portland at 35, Lillard faces a different situation. The Trail Blazers are focused on developing their young talent and rebuilding their future, while Lillard is looking to prove he can still play at a high level despite the Achilles injury. The partnership may not last forever, but for now, both sides are betting that they can find a way to make this chapter work.