Should Damian Lillard Have Followed LeBron James' Path To NBA Titles?

Apr 27, 2025; Milwaukee, Wisconsin, USA; Milwaukee Bucks guard Damian Lillard (0) looks on in the first quarter during game four against the Indiana Pacers of first round for the 2024 NBA Playoffs at Fiserv Forum. Lillard left the game early in the in the first quarter with an injury. Mandatory Credit: Benny Sieu-Imagn Images | Benny Sieu-Imagn Images

The chances of NBA superstar Damian Lillard winning a title before his career ends are slim. After trying to win a ring with the Milwaukee Bucks, he recently returned to play for the Portland Trail Blazers. Lillard failed to reach the NBA Finals in two seasons with the Bucks.

It caused social media influencer Sean Amos to suggest Lillard was too loyal to the Trail Blazers, who drafted him in 2012. Lillard stayed in Portland for 11 seasons before deciding to make a change before the start of 2023-24 season.

Amos makes the point of Lillard should have left Portland years before to win a championship. The closest the Trail Blazers came was when they lost to the Golden State Warriors in the 2019 Western Conference finals.

Amos felt that was the perfect time for Lillard to make an exit like LeBron James did after his seventh season with the Cleveland Cavaliers. After falling to the Boston Celtics, James left Cleveland to join Chris Bosh and Dwyane Wade with the Miami Heat. While the move was widely criticized because James teamed with two of the league's top 10 players, it led to his first title.

James won two championships in four straight appearances in the NBA Finals from 2010-14. It put him among the league's greats. Lillard would probably be in similar discussions if he had a title.

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