Yet, he has never won a championship ring nor has he even come close.
The furthest Lillard and his Blazers have gotten to the Finals was when they made the 2019 Western Conference Finals…and were promptly swept by the Golden State Warriors.
He deserves much better than what he gets in Portland and it has become very apparent that the team’s front office will never deliver.
Right now it feels like only a matter of time before Lillard packs up and moves to another team.
What are the biggest ways that Lillard has been let down by the Trail Blazers – and is it too late to change?
They Didn’t Give Him Defense
The last time a team built around a pair of smaller guards won a championship was over 30 years ago when the Detroit Pistons went all the way.
In other words, the NBA currently isn’t a league that favors smaller teams.
Yet, the Blazers have never done what they should have when it comes to landing bigger, defensive players to complement Lillard and CJ McCollum.
For the last few years, they have had the best big man they’ve ever played with, Jusuf Nurkic, but it is too little, too late.
Jusuf Nurkic finds Damian Lillard for your Heads Up Play of the Day! pic.twitter.com/kkTpagmjMU
— NBA TV (@NBATV) March 8, 2019
If Portland had given Lillard a stronger team long ago they would have already won a championship or two.
They Didn’t Take Him Seriously
The Trail Blazers assumed that Lillard would never leave Portland.
They knew he is a loyal guy and wouldn’t cut and run at the first signs of trouble.
However, they didn’t contemplate that he could ever grow unhappy, but how could he not as he watched other teams rise through the ranks and surpass him?
If the Blazers were serious about keeping Lillard, they would have been serious about keeping him happy and not taking his loyalty for granted.
Speaking of the Billups hiring, that is related to another way the Blazers let Lillard down.
The drama that surrounded Billups was completely avoidable if the front office did proper investigating and spent more time vetting him.
However, they didn’t and it led to a controversy that bogged the team – and Lillard – down.
In fact, it was the first time that Lillard was spoken of unfavorably in the local press which is huge because he has always been heralded as a hero in Portland.
The Billups drama, followed by the Neil Olshey investigation and firing and the bickering and tension behind the scenes, are big distractions that make the Blazers look bad and surely leave a bad taste in Lillard’s mouth.
Damian Lillard has reportedly ‘grown frustrated’ with Portland’s play and tension appears to be on the rise between the players and Chauncey Billups, per @ShamsCharania & @sam_amick pic.twitter.com/Tice1dVmGY
— NBA Central (@TheNBACentral) December 6, 2021
There is no way that all of the chaos surrounding the team isn’t pushing Lillard further and further away and lessening his chances of sticking around.
Lillard is a cool, calm guy and he wants to be surrounded by a cool, calm environment.
The fact that Portland hasn’t been able to give Lillard what he needs is a near-guarantee that he will soon be looking to secure his first ring somewhere else in the NBA.
There is still time to change fate and keep Lillard around but it’s becoming increasingly unlikely, especially since it sounds like McCollum will be sidelined for a while and will leave Lillard to lead the team on his own.
Rumor has it that Lillard wants to play with Ben Simmons and Portland should move heaven and Earth to make that happen or else Dame Time is just about over.