Shannon Sharpe believes Damian Lillard made a mistake not chasing titles, stayed too long in Portland
While Damian Lillard established himself as one of the best guards in the NBA during his time with the Portland Trail Blazers, the team was unable to put together a deep playoff run that cemented the franchise as a championship threat. While Lillard continued to impress, the team was unable to break through and contend for a title.
Year after year Lillard and the Trail Blazers were bounced from the playoffs without an NBA Finals appearance, making it out of the first round just three times in 12 years. During the later stages of Lillard's tenure with the Blazers, there was considerable talk of the two sides parting ways.
For his part, Lillard remained steadfast in his commitment to the team, wanting to win in Portland rather than pursuing a ring. It wasn't until the 2023-24 season that Lillard parted ways with the Blazers, joining Giannis Antetokounmpo on the Milwaukee Bucks.
The way Shannon Sharpe sees things, Lillard made a mistake by not opting to leave Portland sooner. During a recent episode of Sharpe and Chad Johnson's Nightcap show, the NFL vet weighed in on the situation:
"But you know this notion—'I don’t want to link up with nobody, I want to do it on my own.' Man, look, they’re gonna criticize you and judge you anyway.
"Go be happy, man. Damn what people say because they’re gonna talk about you anyway. I’d rather be sad in a Rolls-Royce than riding the bus. So talk about me when I got a ring on my finger, because then I can put one of them in my ear and drown you out."
Check out the comments below beginning around the 7:30 mark.
Damian Lillard recently revealed that he believes he would have won a ring if LaMarcus Aldridge stayed in Portland
While much of Damian Lillard's time with the Portland Trail Blazers was spent competing in the playoffs alongside C.J. McCollum and Jusuf Nurkic, Lillard believes that if LaMarcus Aldridge had stayed in Portland, the two could have won at least one ring together.
At the time Lillard played his rookie season for the Portland Trail Blazers, LaMarcus Aldridge had already found his rhythm in the league, cementing himself as a 20+ point per game scorer while nearly averaging a double-double. The two shared the court for just three years, the first three of Damian Lillard's career.
By the time Lillard had come into his own and found his rhythm in the league, Aldridge was on his way out the door, joining the San Antonio Spurs after the 2014-15 season. The way Damian Lillard sees things, if Aldridge had stuck around, the two would have won at least one ring together:
"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.”
For his part, Aldridge has stated that he regrets how the pair's relationship played out in Portland, saying that he wishes he would have worked harder to have a relationship with the young guard.
As he explained in a 2021 interview with The Athletic, not working harder to establish a relationship with Damian Lillard is one of his biggest regrets.