You can’t make a list of the best point guards in today’s NBA without putting Damian Lillard near the top. His combination of deep range shooting and ability to finish at the rim often leaves his defenders at a loss for how to defend him. He has two of the most highlight-worthy playoff buzzer-beaters in league history, as well as some spectacular offensive showcases in the regular season.

He’s currently in his eighth season in Portland, and while he and the organization appear to be on good terms, the front office has yet to build a team around him with a true chance to compete for a championship. The Trailblazers have tried various roster constructions and failed time and time again. Somehow, in an era of players changing teams constantly, Lillard has remained loyal, evidenced by the five-year max extension he signed in the summer of 2019.

If Lillard, 29, wants to play out the rest of his prime seasons on a mediocre Portland team, he’ll be a Blazers legend for life. He probably already is. If he has loftier individual aspirations, however, he should request a trade elsewhere. With that in mind, here are five reasons Lillard should leave the Portland Trailblazers.

 

1. Rings

(via Sports Illustrated)

The Blazers haven’t had a real shot at a title in all of Lillard’s time with the franchise. Last season was the first time he made it as far as the Western Conference Finals, only to be swept by a banged-up Warriors team without Kevin Durant, and that was probably the team’s best shot at a championship it’ll ever have.

Without a ring, Lillard will likely go down as a great scorer who never got it done. So many others have suffered this fate and it does them an injustice when talking about basketball’s all-time greats. Lillard is on pace for a Hall of Fame basketball career — which isn’t exactly the most exclusive club compared to other sports — but he should also want to taste the champagne at least once.

Lillard is too good a player to never win a ring and be eventually lost to history. His loyalty is respectable. Eventually, though, he should put his legacy above the Portland Trailblazers organization.

 

2. Superteam

(via Fadeaway World)

C.J. McCollum and LaMarcus Aldridge are the two best players Lillard shared the court with so far, and neither particularly complemented his skillset. Lillard’s Blazers teams have been solid teams for most of his career but either lacked offensive firepower or defensive stoppers. He’s been a spectacular individual player and deserves to play with at least one other star on his level at some point in his career.

There are several teams in the NBA that Lillard could join to form a big-three and contend for a title. He’s said before that he doesn’t like how common it is for star players to join forces, so he may be picky with what situation he chooses to join. Still, it doesn’t appear that Portland is poised for a long playoff-run anytime soon.

He could join the Lakers, Bucks, 76ers, and plenty of other squads in need of a perimeter scorer. He only has a few great seasons left, so he should decide sooner than later.

 

3. Big Market

(via Fadeaway World)

Portland is a good basketball city and embraced Lillard since the day he was drafted sixth overall in 2012. One could argue that a player in the modern era doesn’t need to play in a major market to earn major endorsements and recognition because of social media’s massive exposure. On the flip side, if Alex Caruso played for a team like the Magic, Bleacher Report wouldn’t post his highlights nearly as often.

Great players playing for historically-great franchises will always get more attention than those playing in places like Portland. Sure, Portland loves Lillard, but there are more fans of teams like the Lakers and Celtics around the world than the Blazers. In a bigger market, Lillard could grow his brand even more.

Lillard said recently that if he were to be traded, the Lakers and the Knicks are his preferred destinations. Can you imagine what Lillard’s legacy would be if he made the Knicks good again?

 

4. He Deserves To Play In More Big Games

(via CBS Sports)

Even if Lillard does leave and help another franchise become great, that doesn’t guarantee he’d win a championship. What factor it would greatly increase is the likelihood of him playing in more Conference Finals and Finals games.

Lillard is such an electrifying, clutch player and deserves a chance to prove himself on the game’s biggest stage. So many great players throughout NBA history, for a multitude of reasons, never made it to the Finals. Take Tracy McGrady for example, a Hall of Famer who never made it out of the first round until his final season when he rode the bench for the Spurs. It’d be a shame if Lillard never got the chance to play under ultimate pressure. Based on his past playoff performances, he’d likely shine under the bright lights.

 

5. NBA Fans Would Like It

(via Sports Illustrated)

Not every fan wants to see Lillard move, particularly those in Portland, but it’s always fun to see which players get dealt at the trade deadline and during the summer. The recent tendency for players to change teams is both exciting and frustrating, so Lillard should join the trend, especially during the lackluster free-agent class of 2020.

After eight seasons watching Lillard and the Blazers tread water in the Western Conference playoffs, one could argue that fans are getting bored with his time in Portland. Moving teams would reignite interest in Lillard’s career and get more fans following his path, which would likely also increase his merchandise sales and overall brand exposure.

If Lillard wants to stay put, more power to him. It’d be great to see a team like the Blazers get over the hump. It’s unlikely, though, so him forgoing his loyal nature for a great ending to his already stellar career would be a great modern NBA story.

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