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February 20, 2022; Cleveland, Ohio, USA; Portland Trail Blazers star Damian Lillard is honored for being selected to the NBA 75th Anniversary Team during halftime in the 2022 NBA All-Star Game at Rocket Mortgage FieldHouse. Mandatory Credit: Kyle Terada-USA TODAY Sports

'We Would Have Won It' – Portland Trail Blazers Star Has Admission About Potential Title Contention Early in His Career

Originally posted on Hardwood Heroics | By Reign Amurao | Last updated Sep 23, 2025 5:50 PM ET

Damian Lillard is back to where he started his NBA dreams, with the Portland Trail Blazers. Lillard tried to contend with the Milwaukee Bucks the past two seasons. However, the farthest he went with his co-star, Giannis Antetokounmpo, was in the first round of the playoffs. Unfortunately for the star guard, he suffered an Achilles tear in the 2025 playoffs and was waived by the Bucks, which led him to reunite with the Blazers.

Lillard will continue the legacy he started in Portland. With the franchise that drafted him, he holds multiple records. The former Weber State star is the all-time leader in 3-point field goals, the all-time leader in offensive win shares, and the all-time scoring leader.

Since 2012, he’s been working hard to bring the city a championship. He came close in 2019, when he led the Blazers to the Western Conference finals. However, they had to face the Golden State Warriors, who featured Kevin Durant, Stephen Curry, Klay Thompson, and Draymond Green.

“License to Lillard 2025,” the first video that Lillard posted, showed the Portland Trail Blazers player taking a time to think. He played with All-Star forward LaMarcus Aldridge in his early NBA career. With the two of them as partners, the nine-time All-Star thinks Portland had a shot to win the championship.

“I felt like, in the next one or two years, we would have won it,” Lillard said. “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.”

The duo only played together for three seasons. In the 2015-16 season, Aldridge joined Kawhi Leonard and the San Antonio Spurs. Leaving Lillard as the lone star for the Blazers.

Lillard is back home with the Portland Trail Blazers

Mar 27, 2015; Phoenix, AZ, USA; Portland Trail Blazers forward LaMarcus Aldridge (12) celebrates with guard Damian Lillard (0) after making a basket against the Phoenix Suns during the second half at US Airways Center. The Trail Blazers won the game 87-81. Mandatory Credit: Joe Camporeale-USA TODAY Sports

Lillard took the opportunity to spend time with his fans at a recent welcome rally with the Portland Trail Blazers. When he was on stage, the star guard talked about how he felt at home since he rejoined the organization. According to him, he didn’t realize that he was home until he noticed that he didn’t leave to go elsewhere.

“A week ago, that would be about the time I would usually have to pick up and leave,” he said. “And I was like, ‘Man, I don’t have anywhere to go. I’m home.’ That was when it really clicked.”

About Dame time pic.twitter.com/CxQmeheNvj

— Portland Trail Blazers (@trailblazers) September 21, 2025

Fans loved what he said and they love him even more now that he’s back. However, he’ll miss the entire 2025-26 season as he rehabs from the Achilles injury.