1. Shooting
Suppose Henderson, Simons, and Sharpe can't complement each other on the court at the same time. In that case, Simons could eventually be on the move. Veteran beat reporter Sean Highkin of The Rose Garden Report shared a quote emphasizing Simons' desire to win heading into what is somehow already his seventh season.
Anfernee Simons: "We don't want to have another year like this. My sixth year is done now, going into year seven, I want to have the opportunity to win."
— Sean Highkin (@highkin) April 15, 2024
Understandably so, but Simons may be disappointed if he expects this roster to become a playoff contender anytime soon, especially with formidable Western Conference teams like the Warriors and Kings not even making the playoffs. Since Joe Cronin decided not to pull strings to go all-in with Lillard last offseason, how he handles the situation with Simons likely won't be any different.
Even if the Blazers' best shooter stays with the team for the long haul, they still need to become drastically better at spacing the floor. This past season, they were dead last in the league in three-point efficiency at 34.4 percent. The two highest-percent shooters from three are Malcolm Brogdon and Jerami Grant, both veterans who could be on the move as soon as this summer.
Meanwhile, potential franchise building blocks in Henderson and Sharpe only connected from deep at 32.5 and 33.3 percent, respectively. While neither is known to be a great shooter at this stage in their careers, both have showcased flashes of their All-Star upside. Specifically, Henderson's post-All-Star break run this season and Sharpe's end-of-season stretch the year prior.
In the 19 games following the All-Star break, Henderson saw an increase in almost every statistical category, averaging 16.6 points, 7.1 assists, 3.5 rebounds, and 1.3 steals on 40/35/82 shooting splits.
Sharpe's increase in productivity was a combination of his development and his increased opportunity to be a focal point of the offense, with Damian Lillard sitting out for the remainder of the season. Albeit a small sample size, his best run was last April, where Sharpe posted All-Star caliber numbers, averaging 22.8 points, 6.3 rebounds, 5.0 assists, and 0.8 steals per game.
Henderson and Sharpe have shown enough in their early careers for the Blazers to consider their strengths and weaknesses as members of their core moving forward. Since neither player is an elite shooter and relies on their athleticism and ability to drive to create opportunities for themselves and their teammates, the Blazers must find pieces that can optimize their skill sets by spacing the floor.
Additionally, it will give the front office more flexibility to move pieces such as Grant, Brogdon, or even Simons, as the players currently most involved in trade rumors also happen to be their best shooters.
Bonus points if the shooters check all the boxes with their positional size and two-way prowess.