The Portland Trail Blazers may have just pulled off arguably the biggest trade in franchise history by dealing Damian Lillard to the Milwaukee Bucks in a massive three-team deal, but the work in Portland isn't done quite yet. While Jrue Holiday was the main acquisition for the Blazers in the deal, the next move for Portland doesn't involve him — at least not yet.
Re-flipping Holiday makes a lot of sense, but the Blazers would be wise to shop another player who no longer fits with the current competitive timeline in Portland: Matisse Thybulle.
While the Blazers should absolutely look to shop Jerami Grant, a 9-year veteran who should be an attractive piece to contenders given his talent level and locked-up contract, Grant won't be eligible to be traded until December 15th. It doesn't make sense for the Blazers to pay Grant $160 million over the next five years while they rebuild, but they'll have to wait a few months before shopping him.
What's next for Portland on the trade market
Trading Matisse Thybulle is a smaller move, but the 26-year-old should draw attention on the trade market after the Blazers matched an offer sheet the Dallas Mavericks signed him to in July. While Thybulle can't be dealt to the Mavericks for a full year, Thybulle can be moved to another contender after October 5th (3 months after being signed) for a draft pick or a player with a higher ceiling.
Thybulle is a truly great defender, being named to the All-Defensive team twice despite never playing more than 25 minutes a game for the Philadelphia 76ers. Portland doesn't need to move him necessarily, but rebuilding teams are usually wise to clear salary and use minutes on rookie-scale, controllable players instead of known veteran entities. It's possible that Thybulle raises his trade stock early in the season in an expanded role with Portland, but shopping him now to contenders desperately in need of a defensive wing could bring back a key piece for the rebuild.
Thybulle is only due $10.5 million this season, which should make him easy to deal to most teams around the league. Where Thybulle is dealt ultimately is up to him, as he has the right to veto any trade destination for a whole year since he was matched by Portland in restricted free agency. Whether or not Thybulle would actually want to go to a contender matters here, but you can assume that playing a role on a potential title team would be more attractive than playing for a team that's rebuilding in the wake of the Damian Lillard trade.
While it's within the realm of possibility that the Blazers decide to keep Jrue Holiday and attempt to make the playoffs with Scoot Henderson, Anfernee Simons, Holiday, Thybulle, Shaedon Sharpe, it seems more likely that Portland will clear up their backcourt logjam and play for the future by re-trading Holiday. Moving Thybulle first might tip Portland's hand, but it also could generate some real offers and eliminate some of the expected low-ball offers Portland will be getting (or already is getting) in return for Holiday.
What might be most likely for Portland is to set a high price on Thybulle in trade offers, and insist on a first-round pick. It seems highly unlikely that any contender will part with such a valuable asset for a role player, but the Blazers shouldn't be in a rush to move the 26-year-old wing, as he's theoretically young enough to grow with Scoot Henderson and contribute down the line for the Blazers.
But make no mistake about it: making players like Jrue Holiday, Jerami Grant, and Matisse Thybulle available on the trade market is the right move for a Portland team that can't reasonably contend for a title with this current roster. Rebuilding and starting the youth movement behind the No. 3 pick in the 2023 draft in Henderson is the way to go, and trading Matisse Thybulle can fit into that plan just as well.
After being locked into relative mediocrity with Damian Lillard, Portland is finally free to blaze a new path moving forward. But there's still plenty of work to be done in Portland.
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