Dame Time Up In Portland?

Piece by: Nicholas Cosmai

Player loyalty in sports is decreasing at an increasing rate. What once used to be so common has today become something that makes a player so much more likeable. Not just by the fans of that team, but also gaining respect from the rest of the league. In any sort of job, sometimes loyalty can wear thin, and it becomes a decision about whether or not its time to advance your career. Even when you know it most likely will not happen at the place you are at. This crossroad is evident in sports and can be amplified by the large microscope some professional leagues are under, particularly by the media. Damian Lillard is now approaching a decade in Portland and every time they have been knocked out the same question arises. Is the time now for Damian to look elsewhere?

As most people know in the NBA, small markets struggle with bringing in and keeping star players happy. They usually rely on being able to draft exceptionally well to build up a team for the future. What makes it harder for those teams is keeping them when things are not trending very well. Portland is an example of this, in Damian’s time in Portland, his best teammate when he was drafted was LaMarcus Aldridge and now ever since he was traded, it has been CJ McCollum. He has never been able to play in Portland with a perennial all-star.

In relation to this, he has never been the type to try and form a ‘super team’ or a ‘big 3’ in Portland. Many thought that in 2019 when his contract was expiring that he would put the pressure on the front office to bring him more help. This was not the case and he ended up signing a four-year max contract. Damian, with not enough help from a number two, has been able to carry his team to the playoffs multiple times including a western conference finals appearance against a stacked Golden State Warriors team.

Damian is contracted through until the end of the 2024-25 season, but it would be ignorant to think that yet another disappointing playoff exit will not get him wondering. This season, of course, they went out in six games against the Denver Nuggets, but it was more so about how they went out. Damian ended up playing over 41 minutes per game (which is still number one in the league in the playoffs) and averaging 34 points and 10 assists per game. What most likely could heighten the frustration for Damian would have been game five in their matchup against the Denver Nuggets. Not only did he hit a buzzer beater three to send it to overtime and again to send it to double overtime, but he also dropped 55 points and 10 assists. He also scored their last 28 of 46 points and also assisted for eight points in that period too. A game like this can certainly make your mind wonder, it happened with Kevin Durant in OKC after they blew a 3-1 lead to the warriors in the 2016 western conference finals. It happened to LeBron after the 2018 finals where he had one of the greatest runs in playoff history and it was not enough.

This is only the most recent example of Damian potentially being frustrated with his teammates. It has been reoccurring every time the blazers exit the playoffs. As previously mentioned, he is not the type of player that looks to form super teams in Portland and certainly not anywhere else. He even threw Kevin Durant shade for moving to Golden State and said he would never do such a thing. So yes, it would seem highly hypocritical for him to move. Regardless, Damian now is in his thirties, the clock is ticking, and he would 100% want that championship ring. For himself, how long will he have to play at an exceptionally high level? It would be wise for him to have a proper conversation with the front office and ownership just like Giannis did last off season. They need to go and get Lillard a proper star to consistently help him shoulder the load.

If Portland is unable to bring more support for Lillard, it could be time to seriously consider what is most important for Damian for the remaining years of his career. Of course, it is assumed that this is a championship, and he may have to hold out in order to be dealt where he wants to be dealt. There is no question that if Lillard requested a trade tomorrow, there would be 25 plus teams giving Portland a call. No matter what happens though, the moment Lillard retires, the Trail Blazers will begin preparing a jersey retirement ceremony. He is one of two players to hit multiple series ending buzzer beaters with the other being Michael Jordan. He is as clutch as any player currently in the NBA along with his insane shooting range and scoring volume. There are plenty of teams that could do with another volume scorer and if Portland doesn’t get one to pair with Damian, they are definitely at risk of losing him.