As the summer days drag on, there is a very interesting scenario brewing in Portland: The Blazers are rostering four potential All-Star guards. This could be a desirable situation or a dire situation depending on how you look at it. The desirable part of this situation is Portland has boatloads of both current talent and future talent at the guard positions. The dire part of this situation is that Portland has no size, length, or defense for that matter. In a league where size and length is so prevalent, Portland has major work to do from a roster construction standpoint. But from a talent accumulation standpoint, Portland has done exceptionally well. But that is the difficulty of building out a championship-caliber roster: you need all three of talent, length, and size. That’s why the Blazers find themselves in an intriguing situation. Let’s review how they got there.
For starters, the Blazers have a top 3 PG and an incredibly loyal player: Damian Lillard. Since 2012, Lillard has led Portland on the floor, and Portland has promised to build a contender around him (that still hasn’t happened yet, but that’s neither here nor there). Then in 2018, Portland drafted Anfernee Simons out of IMG. While he was a project early on, he has recently blossomed into a 20+ ppg scorer and Portland’s starting two guard. Then in 2022, Portland drafted Shaedon Sharpe with the 7th pick. Some fans were slightly surprised the team didn’t move the pick for immediate help, but nevertheless, Sharpe had a promising rookie year that has fans salivating at his potential. Finally, in the 2023 draft, the Blazers took Scoot Henderson with the #3 pick. This left the fanbase torn; the Blazers added a massive young talent, but it also put the Blazers into this guard conundrum that must be solved before the season starts. Now, Portland has a major decision on their hands. In the following paragraphs, I’m going to address the pros and cons to keeping or trading each guard.
Damian Lillard should be non-negotiable when trade talks occur, but Lillard controls his own future and has expressed discontent with the front office’s decision-making recently. Portland management has reiterated multiple times that they are committed to building around Lillard; however, their actions have portrayed the opposite. And the biggest piece of evidence for this was the decision to draft at #3. Portland had an opportunity to trade for a big-time veteran star in exchange for #3, but Portland stood pat and drafted Henderson. The optics could not have looked worse for the relationship between Lillard and the front office. First, Joe Cronin and company promised Blazer fans that they would make a win-now move to give Lillard help. That didn’t happen. Secondly, Dame has expressed his desire to play with veterans, and he has vehemently proclaimed that he doesn’t want to play with youngsters. That hasn’t happened yet either. Finally, Portland took a guard with #3, and many people view Scoot as Dame’s possible replacement. Like I said, bad optics. Thus, if Lillard wants out, you must respect it. Teams that could put a package together for Lillard include the Heat, Nets, and 76ers. However, the packages are underwhelming at best, and Portland must be sure that they get sufficient assets in return. However, if Lillard continues to be loyal and wants to stay in Portland, you must keep him and build around him. A top 75 player of all time doesn’t come around often, and Lillard gives you the best chance to win a title. The onus is on Cronin to give him help. Thus, my preference is that Lillard stays a Blazer and continues to lead this team, as long as Cronin gives him help for once.
Verdict: Keep
Anfernee Simons is the next guard in the Blazer rotation. Simons has made major strides since his rookie year, and he is now one of the best young guards in the league. He can create his own shot off the dribble, hit threes with the best of them, and he is super athletic. If size wasn’t an issue, I would love to keep Simons. However, there is one key factor to Simons’ value and potential to be traded: his contract. Simons is making $100 million over 4 years, which makes his contract valuable when trying to match salary in a trade. For the Blazers, this is a vital piece because in order to get a second star to pair with Lillard, you must match salary. Simons’ contract does that perfectly. It is unfortunate, but Simons’ skills and play style is expendable in the current iteration of the Blazers: Sharpe is younger and has more potential and Lillard is just flat out better. In addition, Simons is young and should have value to other teams. I would love to keep him, but he seems like the perfect trade candidate, especially when Portland is after a forward with star power.
Verdict: Trade
Shaedon Sharpe might be the guard that has the most potential in the NBA. Drafted #7 out of Kentucky last year, Sharpe has rare athleticism and a silky shot. Last year, once the Blazers started tanking, Sharpe had multiple 20+ point games. He proved he has the makings of an elite scorer. If you compare Sharpe to Simons, Sharpe is younger, more athletic, and cheaper. Currently, Sharpe is not the better player when compared to Simons, but Sharpe’s potential is what makes Portland and other teams excited. In addition, Sharpe is a healthy 6’5”, which is important when putting a guard next to Dame. We all know that CJ and Ant are smaller guards, and it’s been well documented that Portland needs size around Dame. Sharpe doesn’t have the perfect height, but 6’5” is a whole lot better than 6’3”. Because of Sharpe’s height, potential, and age, it would be extremely wise for Portland to hang onto him and watch him grow. The only way it would be reasonable for Sharpe to leave Portland would be if he was included in a trade for a massive, massive talent. Think Joel Embiid level talent. And because that is probably not going to happen, I think Sharpe is a Blazer next year. Portland would be wise to keep him.
Verdict: Keep
Finally, let’s discuss Scoot Henderson. Scoot, to no fault of his own, is the player that really turned this situation into a conundrum. In all honesty, I’m not sure what Portland should do with Scoot, and quite frankly, I don’t think Portland does either. In a press conference following the draft, GM Joe Cronin stated that they are more interested in accumulating talent rather than focusing on fit. Well, Scoot Henderson passes the talent test, but in terms of fit, it couldn’t be worse. If Portland keeps both Dame and Scoot, how many minutes will Scoot play? If you are giving your #3 pick less than 15 minutes a game, that is terrible asset management. On top of that, Scoot’s growth would be hindered. In my opinion, Scoot’s future with Portland is based off of Damian Lillard. If Lillard asks out, Scoot will be given the keys to the franchise. But if Dame stays in Portland, I don’t see how Scoot and Dame can co-exist. I could be wrong, but I don’t see the upside in bringing Scoot off the bench and hindering his development. In addition, Scoot and Simons could net the Blazers an absolute haul in a trade. This would give Lillard immediate help. Henderson has incredible value around the league; he is seen as the next great NBA guard. Admittedly, it is unfortunate that the Blazers have to “pick” between Dame and Scoot, but if Portland wants to compete with Dame, tough decisions need to be made.
Verdict: Depends on Lillard’s decision
It is safe to say that Portland is in an intriguing situation. It is a great situation in the sense of having assets: the four guards in Portland are uber-talented. But, it is a grim situation because the roster fit is abysmal and the Blazers still don’t have size. It is clear that Portland must do something before the season starts for multiple reasons. If they want to build around Dame, one or two of the guards must go in exchange for help. Additionally, four guards won’t win a title, so Portland must balance out the roster if they want to compete in any way. Let’s see what happens.
Let us know in the comments who you think Portland will trade. Do you think Portland will make any moves at all?