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The Portland Trail Blazers entered the 2025 NBA offseason looking to shift their focus to their young core. The Trail Blazers moved on from Deandre Ayton and sent Anfernee Simons away to clear minutes for Donovan Clingan and Scoot Henderson. However, Robert Williams III and Jerami Grant will continue to steal minutes from Shaedon Sharpe and Yang Hansen.
As the regular season went on, Portland head coach Chauncey Billups began to give his young players more burn. Clingan grew into his own before his very eyes and will likely be the starting center in front of Williams III next season. However, the fact that Grant and Jrue Holiday are on the roster sends differing messages. Are the Trail Blazers trying to compete or tank?
Holiday was re-acquired in a move that was more of a salary dump by the Boston Celtics than anything else. He failed his physical, resulting in Portland taking back the draft picks they traded away for him. If he starts the year as the starting point guard, Henderson's development could be even more stunted.
Despite that, Grant and Williams III are the two biggest problems. Both Trail Blazers could have been moved earlier this offseason, but it is too late for their larger contracts to be moved easily. Grant had a market, but his contract is so large that the list of teams able to trade for him was not as long as the teams that would have been interested in adding him.
While the team's direction is clear, their execution is questionable. Portland just saw a division rival, the Oklahoma City Thunder, ride their rebuild into a championship. It is possible to build through the draft and make smart trades, but the Trail Blazers need to be a bit more assertive.
Why the Trail Blazers should have traded Grant and Williams III
Williams III has one more year on the four-year, $48 million contract the Boston Celtics gave him in 2022. His expiring contract will be one to watch at this year's trade deadline. If he can stay on the floor, he is a relatively cheap option at center for contenders. However, Williams III's injury history is lengthy and he cannot be trusted to stay on the floor.
Grant presents a very similar problem, with one key difference. The forward has not played in more than 63 games in a season since 2019-20. Grant was shut down with injury last season after appearing in just 47 games. He is in the third year of a five-year, $160 million contract he signed in 2023. At this point he is almost guaranteed to pick up the player option in the last year.
While Grant's contract is one of the worst in the NBA, the reasoning behind it is strong. At the time, Portland was trying everything it could to retain Damian Lillard. However, the franchise legend requested a trade after Grant signed his deal. The Trail Blazers were left with an oversized contract for a player who is not in their long-term plans.
Both of these players could find new homes later this summer or at the trade deadline. However, making such deals is easier in the early part of the offseason amid the chaos of free agency. Now, Portland will have to work harder to convince other teams to make trades with them. At the end of the day, the Trail Blazers' indecision shot them in the foot.
Williams III will come off the bench next season. However, Grant's talent and is contract are too much to justify a bench role.
Where do the Trail Blazers go from here?
The Trail Blazers had the right idea in the second half of the season. Sharpe began to show flashes of the scorer he could become down the back stretch. He and Henderson represent the future of Portland's perimeter, along with Camara. If Clingan continues on his current trajectory, he could be the next great defensive anchor in the league.
Billups has a lot of intriguing young talent to work with. Hansen was one of the biggest reaches during the NBA Draft, but his ball skills make for a fascinating development challenge. If he hits, the Blazers have six solid young pieces that can grow together. The Thunder proved that a strategy like that can work if the team has the right culture.
Holiday and Grant are the veterans that will help hold the team together, even if they are overpaid. Their roles on the team are similar to what Khris Middleton, CJ McCollum, and Marcus Smart are to the Washington Wizards. If both teams have their way, the veterans will help their young counterparts acclimate to the league and then fetch their team future assets in trade.
Unfortunately, their contracts hamstring the Trail Blazers until they are either off the team or expire. With the Western Conference as competitive as it is, maybe letting the contracts play out is not such a bad idea. If their young players continue to develop, Portland could sic them on the league surrounded by premier role players in a couple of seasons.
Regardless of what happens, not moving Williams III and Grant is the biggest mistake of the Trail Blazers' offseason so far.
