July 1 update: Damian Lillard has requested a trade from the Blazers, so it appears he’s going to the guard going out. He was not expected to pursue this path, so his chances of being dealt appeared to be low. However, the trade request has been put forward and we can now boost his chances of being dealt to 99%.
With the conclusion of the 2023 NBA Draft, the focus in the league now shifts to free agency and the possibility of bigger trades. As the new league year begins and a new CBA comes into play July 1, some teams will be looking to make moves to improve their short-term prospects while not completely sacrificing their long-term plans.
One such team trying to thread that needle is the Portland Trail Blazers. The Blazers missed the playoffs in each of the last two seasons, making it the first time in Damian Lillard’s career he’s missed postseason play in back-to-back years. Lillard is the franchise’s icon, and he’s been in trade rumors over the last few years as he enters the final stage of his career. The point guard is on a huge contract and has a $63 million player option for the 2026-27 season, so the Trail Blazers seemingly would need to make moves now to avoid being hamstrung too much by the salary cap later on in this deal.
Lillard has reportedly given the team a chance to improve the roster before demanding a trade. The guard has been diplomatic for the last few seasons about the performance of the team, but even he is slowly realizing he may need to leave in order to have a serious chance at a ring. The Blazers took guard Scoot Henderson with the No. 3 overall pick in the 2023 NBA Draft, giving the team four high-usage guards. We’ll take a look at each player and the likelihood he gets dealt this summer.
Lillard averaged a career-high 32.2 points per game last season. His usage rate was 33.8%, which is also a career high. The guard will be 33 entering the 2023-24 season, so he’s theoretically a bit past his peak but still very much considered a star. Injuries have been a concern over the last few seasons with Lillard, but the Blazers have also shut him down when they realized they were out of contention.
Both Portland and Lillard, from all the reporting, want to avoid a split. Unless Lillard demands a trade, the Blazers aren’t going to deal him. And Lillard likely won’t do that barring an offseason where the team makes no moves. Portland is unlikely to run things back with this roster as currently constructed, so the likelihood Lillard gets dealt is probably around 5%.
The rising guard had a career-high 21.1 points per game. He’s a lethal three-point shooter and has maintained a good percentage with an uptick in volume. At 24, Simons likely has a few more seasons to develop. His 25.1% usage rate is a bit problematic in the context of the team, especially if Henderson and Sharpe getting more touches is a priority for Portland. Simons is also a negative defender by every metric, which makes him likely to dealt. His contract is sizable but not a hinderance in trade negotiations. There’s a belief he can take a step forward as a lead guard, which makes him appealing to teams. The likelihood Simons gets dealt is at 50%.
In his final 10 games of the season. Sharpe averaged 23.7 points, 6.1 rebounds and 4.1 assists while shooting 46% from the floor and 37.8% from deep. That’s an encouraging sign for the Blazers regarding his development, although Portland went just 2-8 in those games. The team is unlikely to give him up, and his trade value is hard to gauge since he didn’t have a big role until the end of the season when the team was out of contention and basically trotting out G League lineups. The likelihood he gets dealt is somewhere around 15%.
Henderson is considered by many to be the second-best prospect in the draft, and he’s got the tools to be a lead guard for any team. The Blazers have reportedly said they believe the addition of Henderson would be more impactful than any other move they could’ve made with the No. 3 overall pick. Defensively, Henderson could make an immediate impact for Portland in the backcourt. He’s a good trade chip and teams will want him if they are taking on salary in a trade, but the Blazers value him highly. The likelihood he gets dealt is 5%.
The most likely outcome for the Trail Blazers next season is a three-guard lineup with Lillard, Henderson and Sharpe. Jerami Grant is a priority in free agency, and the Blazers won’t be operating as a team over the second apron in the new CBA. That means they can package Simons and Jusuf Nurkic in trades, and take on more salary than they are sending out. The question is whether there’s a player out there who not only fits Lillard’s timeline to compete but also fits the roster. The Blazers can’t trade their 2024 or 2025 first-round pick, but they have their full arsenal of first-round picks after that.
Deandre Ayton and John Collins feel like the most logical trade targets, but the Blazers could aim bigger by inquiring about Pascal Siakam and Nikola Vucevic. Vucevic would have to come in a sign-and-trade agreement, since he’s a free agent. If Zion Williamson becomes available, that’s another player the Blazers could look into acquiring.