Damian Lillard looks to be a surefire Hall of Famer, potentially the best player in the history of the Portland Trail Blazers, and one of the greatest guards of all time. So the question is, how did he get here, and what is next?

Lillard bounced around three different high schools before finding success at Oakland High School in California. He was not highly recognized and committed to Weber State in the Big Sky conference as a two-star recruit out of high school.

Lillard exploded onto the college scene winning Big Sky Conference Freshman of the Year and being named to the first-team All-Big Sky. He followed that up by averaging 19.9 points per game and leading his team to a Conference Championship. He also won Big Sky Player of the Year as well as being named an All-American by the Associated Press. 

Lillard was not done, returning for his redshirt junior season to average 24.5 points per game, good for second in the nation, was named to a third Big Sky first-team All-Conference and won a second Big Sky Player of the Year award. He finished his career at Weber State as the No.2 scorer in school history and fifth in Big Sky history before entering the 2012 NBA Draft. 

The Trail Blazers took him with the sixth pick in the first round. In his rookie season, Lillard continued to dominate, winning the NBA Rookie of the Year Award. In his second season, he was selected to his first all-star game and received his first All-NBA selection. 

Lillard would then clinch his first division title in year three, before being eliminated in the first round of the playoffs. The Trail Blazers knew he was the guy, and inked him to a five-year, $120 million contract extension. He paid it off by becoming the fastest player in NBA history to reach 600 threes made in just 247 games.

He would go on to break the franchise record for career threes with 827 and became the first Blazer to rack up 400 assists in each of his first four seasons. After advancing to the second round of the playoffs, the season would end. 

In year five he joined Michael Jordan and LeBron James as the only players to reach 8,000 points and 2,000 assists in their first five seasons. Lillard would also set the franchise record with 59 points in a game and became the fifth Blazer to ever record 2,000 points in one season. Despite a first-round exit, Lillard earned the Magic Johnson Award for excellence on the court and with cooperation and dignity in dealing with the media and public.

In the 2017–18 season, Lillard received his first All-NBA first-team selection and was fourth in MVP voting after finishing top five in the league in scoring. And after a rough postseason, he bounced back strong in the 2018–19 season going the farthest he has ever gone in the playoffs, just coming up short in the Western Conference Finals to the Golden State Warriors. It was the first Western Conference Finals appearance since 2000 for the Trail Blazers.

Lillard set a new franchise record for threes in a season with 229, became the first Blazer to ever have 2,000 points and 500 assists in one season, and set the record for most games in Blazer history with 30 points and 10 assists. In the 2019–20 season, he would be named to his fifth all-star team, and recorded three 60-point games, tying Wilt Chamberlain for the most in one season.

This season Lillard set the record for most points scored in Blazer history with 18,040 on Dec. 19, 2022. On Jan. 25, he recorded his fourth career 60-point game, becoming the fifth player to ever do so. Lillard this season has moved up to sixth on the all-time list for threes and was named Western Conference Player of the Week last week. He reached the 5,000 assist mark Monday night, the second most in franchise history.

Lillard was named to the NBA’s top 75 players of all time list in 2021, but he still does not have one thing: a ring. Despite being one of the most loyal players in the league, the question of his future in Portland remains, with fans and analysts riding the fence. Gunner Scott Miller, a junior WSU and a die-hard Lillard fan, said he loves him, but he needs to move on to succeed.

“He means everything to us fans, his loyalty over the years is inspiring knowing what type of basketball super-teams there are nowadays,” Miller said. “As a Portland fan, I’ve wanted him out for years. I want him to contend. I love him but he will never win in Portland. He is a generational talent on a weaker franchise. I hope to see him succeed, I am a fan of Lillard wherever he goes.”

Fellow fan Evan Charney, who is also a junior at WSU said he hopes he stays but that he deserves to chase a ring and no one would blame him if he did. Lillard is 32 years old now and still producing at a Hall-of-Fame level, but how long does he have, and what is the right move for Lillard?

The Blazers continue to do all they can, whether it is trades or $50 million, but they still are not contending. All we can do for now, is sit back, and watch the legend of Damian Lillard continue to unfold.