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Trail Blazers: When does legacy overpower loyalty for Damian Lillard?

By Carson Brown

MIAMI, FLORIDA - JANUARY 05: Damian Lillard #0 of the Portland Trail Blazers reacts against the Miami Heat during the second half at American Airlines Arena on January 05, 2020 in Miami, Florida. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Michael Reaves/Getty Images)
MIAMI, FLORIDA - JANUARY 05: Damian Lillard #0 of the Portland Trail Blazers reacts against the Miami Heat during the second half at American Airlines Arena on January 05, 2020 in Miami, Florida. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Michael Reaves/Getty Images) /
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Damian Lillard has set himself up to have an all time career with the Trail Blazers, but he needs that ultimate honour of being an NBA Champion.

No matter what he accomplishes in the second half of his career for the Trail Blazers, if there is no championship ring somewhere in there, then his name will always have an asterisk next to it as one of the greats who could never get it done.

As much as I hate to say this as a die-hard Blazer fan but you have to think that Damian Lillard understands this. No superstar wants this next to their name. To be the player who could never figure it out and win at the highest stage.

When you really think about it, how many of the greats out there who never won a title stuck with the team that drafted them? Charles Barkley switched teams three times, Allen Iverson thought a young Melo could do it for him leading to him demanding a trade, and Karl Malone even ring-chased in his later years and teamed up with Kobe Bryant and Shaquille O’Neal.

At what point does Dame call it quits as a Trail Blazer? He preaches loyalty and the drive to bring a title to Portland but somewhere along the way he has to reach a breaking point. Where being the small market player that nobody takes serious as a contender gets old.

Even Dirk Nowitzki was said to be ready to leave Dallas if he didn’t get that one ring that defines his career, but thankfully he pulled that off. Dame is 29, not 24. He’s in the midst of his prime and only has so much time left to be playing at this level.

Next. 4 players most likely to be moved before trade deadline. dark

Writing this brings me pain but I’m just being realistic. As much as I love and respect Lillard, I am worried that the day he demands a trade may be sooner than later. Dame is the best healthy point guard in the NBA at the moment and it’s going to get him nowhere.

Just take a second and imagine him alongside Giannis Antetokounmpo in Milwaukee or pairing with Luka Doncic in Dallas. Those teams are unquestioned contenders that would go crazy about the opportunity to have Lillard. And to say it again, I’m a die-hard Blazer fan and respect what Damian Lillard has done for Portland and the Trail Blazers but it may be time for him to get his…