The Portland Trail Blazers find themselves at a crossroads. The young core is already established, and the team has more than $75m in estimated 2026 cap room, so the offseason presents a chance to turn the page on rebuilding and start competing. The following three strategic moves could be key to transforming the Blazers into a playoff threat.
1. Flip Jrue Holiday for Shooting
The acquisition of Jrue Holiday by the Blazers showed the direction of a winning team, but $104 million and a three-year contract are restraining options. Trading Holiday at the moment would create roster space and alleviate the playing time of up-and-coming youngsters such as Scoot Henderson and Shaedon Sharpe.
On the same note, Robert Williams III is available on the trade block, and his salary of $13.3 million could save and earn role players or draft picks. The first order of business: pay the salary, and then it becomes an emergency to bring in a catch-and-shoot wing of the highest quality, which Portland could not even crack the top half of the league in catch-and-shoot percentage with anybody but Anfernee Simons.
More spaced and stronger offensive teams tend to overachieve, particularly against the spread, and lines are often moved at sportsbooks depending on roster movement and offensive numbers. A knockdown shooter trade would not only help Portland in the real-world success but also their dependability from a betting perspective. As a fan and bettor, it is critical to monitor such moves on the roster. Salient betting analysis and forecasting of such moves are available by Cheekypunter, a leading source in the analysis of sports betting.
Impact: Cap relief and a sharpshooter would tremendously help floor spacing and offensive efficiency, and the young core would be more efficient.
2. Trust Youth: Promote Clingan and Hansen Thrive
DeAndre Ayton has agreed to an out-of-season buyout, which will release $25 million and minutes at the centre. That clears the way for Portland to prioritize Donovan Clingan and the rookie Yang Hansen. Clingan has defensive instincts as a rookie, and Hansen, who has received some criticism on draft night, will need legitimate development time. The Blazers cannot afford overworking the frontcourt and should allow these young bigs to learn to be confident and to have rhythm and experience.
Impact: The growth of homegrown talent enhances the long-term upside, reinforces the defensive presence, and saves the cap space to add players later.
3. Use Cap Space + Draft Capital on Getting a Consistent 3-and-D Wing
Having flexibility in their finances and veteran contracts in-house, Portland is in a good position to seek a veteran 3-and-D wing in free agency or through trade. According to analysts, the Blazers could sign a productive floor-stretcher at the position via their mid-level exception as the latest addition to their team. They could trade up-and-coming draft capital, too, and pair picks to trade in a market that is becoming more spacing and shooting-oriented.
Impact: A straight perimeter shooting skill would open the court, improve the spacing in offence, and give easier opportunities to Henderson, Sharpe, and others.
Final Word
Scoot Henderson, Shaedon Sharpe, and Donovan Clingan form a good young core, but they have to have some structure to make it in the stacked Western Conference. Through trading big contracts like Jrue Holiday or Robert Williams III, it is possible to create space and get better-fitting role players. Youth development will help with growth in the long run and find their identity, particularly in the frontcourt. Lastly, they would want to procure a solid 3-and-D wing who can make them more balanced in offence and competitive as a team. When properly done, these three steps can bring Rip City back to relevance and to a sustainable formula back to postseason relevance.
In a perfect world, but what you fail to mention is who would they get, and how would they get them? It is easy to say what they should do, but it is harder to write a realistic option.