The Damian Lillard situation in Portland is very complicated. The Trail Blazers haven’t always operated in a sense of championship window. Signing guys like Evan Turner and Allen Crabbe to 4yr/$70+ million deals in the summer of 2016 have come back to bite them. First round exit after first round exit starts to wear on any player, especially one of Lillard’s caliber. Now, he reportedly is not a huge fan of the Chauncey Billups hiring as he was not asked for his intel. It is starting to become messy, and having a superstar in a messy situation is never a good thing. Where have the Portland Trail Blazers gone wrong? Can they fix it and if so how can they keep Lillard in a Portland uniform for the rest of his career or even just for next season?
In 2012, the Portland Trail Blazers had the 6th pick in the draft, along with the 11th pick. At 6, they drafted guard Damian Lillard out of Weber State, that pick worked. At 11, they drafted big man Meyers Leonard out of Illinois, over the likes of Evan Fournier, Draymond Green, and Khris Middleton. Leonard has had a subpar career averaging 5.6 points and 3.2 rebounds over 9 seasons with the Blazers and the Miami Heat (he was traded to and waived by the Oklahoma City Thunder in March after using an anti-semitic slur). In 2013, the team drafted guard C.J. McCollum out of Lehigh University, a massive hit. McCollum has become a dynamic player in the backcourt with Lillard. Over the past 6 seasons McCollum has averaged 21.9 points and 4.0 assists on 45% from the field, 40% from 3 point range, and 82% from the free throw line, becoming one of the better guards in the NBA. On February 19th, 2015, Portland traded Will Barton and a first round pick to the Denver Nuggets for Aaron Afflao, Afflao would leave the team as a free agent and Barton has become a vital team to a really good Denver Nuggets team. That summer, disaster struck, as multi-time All-Star LaMarcus Aldridge departed from the team, signing with the San Antonio Spurs. In 2016, the NBA saw a salary cap spike, so what did Portland do? They would sign Evan Turner to a 4yr/$72 million dollar deal and matched a 4yr/$75 million offer sheet that guard Allen Crabbe signed with the Brooklyn Nets, Crabbe was traded to the Nets the very next summer for Andrew Nicholson, who never played for Portland, a disastrous offseason. They traded up in the 2017 draft to draft Zach Collins, over Donovan Mitchell, Bam Adebayo, and John Collins. Center has been a revolving door, they signed Enes Kanter in the buyout market, then traded for Hassan Whiteside, and traded for Enes Kanter after he left the team as a free agent. They traded 2 first round picks for Robert Covington to try and help the defense, but he didn’t. This is a team who continues to make moves that are mediocre, so why would they ever expect to be anything above just that, mediocre. They did trade Mason Plumlee for Jusuf Nurkic and a first round pick, so that was smart.
The Portland Trail Blazers have made mediocre moves, which leads to mediocre results. Over the past 5 seasons the team has advanced out of the first round just once, and when they did, they were swept out of the Western Conference Finals in 2019. They have been swept three times, twice out of the first round, since 2017. They lost in 5 games, losing 4 straight to be eliminated in 2019. They were bounced by a depleted Denver Nuggets team, one that would be swept the very next round. They have not done anything drastic to improve the roster over the past couple of years, so why would the results ever change? Now, here we are, the star of the team might just be looking for a new home, how can Portland try and salvage the situation, if it is salvageable at all.
Portland was 29th in defense this past season, only better than the Sacramento Kings. That needs to improve, the coaching change should help. However, the roster needs to improve as well. Well, a first team all-defensive player might have become available on the trade market. Ben Simmons did have a rough series against the Atlanta Hawks but Portland should still try to trade for the 24-year-old forward. Would the Philadelphia 76ers take guard C.J. McCollum in a trade? I think so as they need a guy who can put the ball in the basket. However, McCollum simply is not an NBA point guard, he has not been a good enough passer during his career to say that he is. Maybe with more opportunities McCollum could become a better playmaker but I am not too sure about that. The Sixers would probably want something extra with McCollum in the trade so Portland could add a draft pick to the trade to get it done. Another thing the Blazers can do is not re-signing Enes Kanter, because that dude is terrible at defense, and replace him with a better defensive player. If Simmons become available, Portland needs to strike in that department. However, what if Lillard did ask for a trade out of Portland?
Here is the first thing about a Lillard trade demand, he is about to have a 4yr/$176 million dollar contract extension kick in which is why from a quick glance a demand feels unlikely. However, that final year is a player option and he is going to be 31 in July. 3 years feels much shorter then 4 and to go along with the fact that we just saw James Harden demand out of Houston with 2 years plus a player option left on his contract, something Kyrie Irving also did in 2017, a trade demand does not feel as unlikely anymore. So now we have to ask the question: what could Portland get in a Damian Lillard trade?
What we have seen over the past couple of years from the Oklahoma City Thunder, Houston Rockets, and New Orleans Pelicans, is that acquiring boat loads of draft picks is what teams want to do, and hope that one of the picks becomes the next face of your franchise. Portland could absolutely go that route. Maybe the Knicks offer every pick and swap rights they own unprotected to go along with R.J. Barrett, Obi Toppin, and Immanuel Quickley in a trade. That is around 10 draft assets, as the Knicks also own a few Dallas Mavericks picks. The Celtics could offer Jaylen Brown plus picks, which seems like the best offer there might be. Maybe the Pelicans try to get involved, they have a ton of future picks, along with players like Brandon Ingram, Nickeil Alexander-Walker, Kira Lewis, and Lonzo Ball in a sign-and-trade. The Lakers would be laughed off the phone with Kyle Kuzma, Talen Horton-Tucker, the 22nd pick and the 2 future picks they could put in a trade. The 76ers could try and create an offer of Ben Simmons, Tyrese Maxey, and Matisse Thybulle plus a bunch of picks, but they owe a pick to the Thunder due to the Al Horford for Danny Green trade. Teams would line up to try and acquire Damian Lillard in a trade and the return Portland would get in any trade would be massive.
The Portland Trail Blazers have been a mediocre team for years now. They have been eliminated in the first round 4 out of the past 5 seasons, winning just 3 playoff games in those 4 first round exits. They need to improve and need to improve fast so they can try and keep star Damian Lillard, though it might just be too late. Lillard is a superstar in this league and has been just stuck in mediocrity during the course of his career, advancing in the playoffs in just 3 seasons and going to just one Western Conference Finals during his career. It has not been good enough in Portland, and now the franchise looks like they are going to pay for it.
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