The Portland Trail Blazers have an active four-year playoff drought that they want to end. If their 33.5 win total projection is any indication, that's unfortunately unlikely to happen this upcoming season. But for whatever reason -- whether it's their end-of-season hot streak, new ownership looming, impatience, an overly optimistic view of their roster, or some combination of these factors -- Portland is adamant about winning immediately.
"It's winning time now for the Trail Blazers. Chauncey [Billups] and I have been saying that since last season," general manager Joe Cronin said.
Before Cronin said that, he made that desire apparent through his actions, deciding to send Anfernee Simons to the Boston Celtics in exchange for Jrue Holiday. Although the 35-year-old guard with championship experience will positively impact the development of Portland's young core, the primary reason to make such a trade is to win now. Why else would you take on an aging guard still on the books for $104 million over the next three years?
But if the Blazers really want to win right away, they should consider trading Scoot Henderson, Shaedon Sharpe, and one of Donovan Clingan/Yang Hansen for a superstar who better fits that timeline.
Should the Blazers sacrifice their young core for a superstar?
After the trade for Holiday and Damian Lillard's exciting return to Portland, the Blazers will have two talented aging stars in the backcourt once Lillard returns from injury, likely in 2026-27. Thanks to the initial Lillard trade with Milwaukee, Portland finally has the complementary pieces around him.
A starting five of Lillard, Holiday, Toumani Camara, Deni Avdija, and Donovan Clingan is enough to make the playoffs even in a loaded Western Conference. But if the Blazers want to become legitimate contenders, they'd still need to find more star power.
If, say, Giannis Antetokounmpo suddenly becomes available, the Blazers are now in a much better position to make an all-in trade for such a player. They could entice Milwaukee with a package that included the Bucks getting their picks back, along with Henderson, Sharpe, and one of Clingan or Hansen. At that point, Camara should even be considered touchable with Jerami Grant and his immovable contract sliding into the starting five.
To be clear, Portland blowing up its young core is an aggresive move that could set back their franchise for years to come. With that being the case, they should only pull this forbidden lever if a superstar becomes available that could truly move the needle for their contention status. But the Blazers have been straddling two timelines for multiple years now, and with the additions of Holiday and Lillard, they continue leaning closer to the older one. Eventually, something will have to give.
Sharpe and Henderson will have every chance to breakout in 2025-26 with Simons gone and Lillard still recovering. But if they don't, it will be even more tempting for the win-now Blazers to pull this forbidden lever.