Damian Lillard is widely regarded as one of the greatest players to ever play Portland Trail Blazers jersey. Yet despite his immense talent and numerous accolades, Lillard has yet to earn a NBA title. Many have speculated about the reasons for this phenomenon, but Lillard himself believes that a pivotal moment in his time with the The pioneers cost him his best chance at winning a championship.
According to Lillard, The departure of teammate and co-star LaMarcus Aldridge in 2015 was the turning point that dashed his hopes of winning it all with Portland.
Reflecting on what could have been, Lillard said on the Club 520 Podcast, “If [LaMarcus Aldridge] “I would have never gone to San Antonio, we would have won at least once by now. I could have blossomed, but he was so good. My freshman year, I started with a pull-up to the elbow after a pick and roll — literally, one-two-three dribbles to the elbow, pull-up every time. Because they were trying to come back at him.”
Lillard and Aldridge: An Unfinished Partnership
When LaMarcus Aldridge retired in 2021, he reflected on his decision to leave Portland, revealing that his relationship with Lillard played a significant role in his departure. In an interview with The AthleticAldridge expressed regret over how things ended between them.

Damian Lillard #0 of the Portland Trail Blazers celebrates a basket by LaMarcus Aldridge #12. Steve Dykes/Getty Images
“I wish Dame and I had talked more and tried to develop a better relationship. Part of it was because he was young, trying to find his way, and I had worked so hard to get where I am. I wish I had worked harder… the only regret I have is that I wish I had worked harder to have a relationship with Dame.”

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Anthony Edwards Makes Surprising Statement About Older NBA Generation and Michael Jordan
THE “what if” The storyline surrounding Lillard and Aldridge continues to haunt Trail Blazers fans, as Many believe the duo had the potential to bring a championship to Portland.
Gianni Taina is a bilingual journalist, fluent in English and Spanish, specializing in soccer, NBA and tennis. He began his professional career in 2020 with Mundo Deportivo US, where he took his first steps as a writer. Gianni has covered major sporting events such as the FIFA World Cup in Qatar, the NBA Finals and Grand Slam tournaments such as Roland Garros. His ability to report on events in real time and write under pressure has established him as a valuable member of a top-level team of journalists. In 2024, he joined Bolavip US, where he covers a wide range of sports, including European soccer, MLS and the NBA. Gianni graduated in Communications from Deportea in Buenos Aires, Argentina.