Damian Lillard is widely regarded as one of the greatest players to ever don a Portland Trail Blazers jersey. Yet, despite his immense talent and numerous accolades, Lillard has yet to secure an NBA title. Many have speculated on why that is, but Lillard himself believes that one pivotal moment during his time with the Trail Blazers cost him his best shot at a championship.

According to Lillard, the departure of his 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] would have never went to San Antonio, we would have won at least once already. I would have come into my own, but he was that good. My rookie year, I started with an elbow pull-up jumper off a pick and roll—like literally, one-two-three dribbles to the elbow, pull-up every time. Cause they were trying to get back to him.”

Lillard and Aldridge: An unfulfilled 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 Athletic, Aldridge 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 just feel like I wish Dame and I would’ve talked more and tried to develop a better relationship. Part of it was he was young, trying to find his way, and I had worked so hard to get to the spot I was at. I wish I would have worked harder… the only regret I have is I wish I would have worked harder to have a relationship with Dame.”

The “what if” scenario surrounding Lillard and Aldridge continues to haunt Trail Blazers fans, as many believe that the duo had the potential to bring a championship to Portland.