5 Worst-case scenarios Trail Blazers must avoid at all costs in 2024-25

4. Portland's established players don't get traded

While the Blazers may be wise to keep Williams depending on his health and trade value, there are some players that they should strongly consider moving before the deadline. Ayton is the highest-paid player on the Blazers roster ($34 million this season), and it's clear that the Blazers are set on making Clingan their future center.

Clingan is six years younger than Ayton and roughly $27.2 million cheaper this year. While Ayton will likely always be a better scorer than Clingan throughout their respective careers, "Cling Kong" impacts winning in ways beyond his scoring, including his rim protection, rebounding, and underrated passing.

It may be hard to find value for Ayton given his contract and the fact that many teams already have their starting center position figured out, but this is a case where the Blazers should move Ayton for whatever they can get for him.

Another starter who doesn't make sense to keep around is Grant. He's the second-highest-paid player ($29.8 million this season) and the oldest player on their roster. The trade deadline is a perfect opportunity for Cronin to move Grant to a contender.

Matisse Thybulle also fits that category, as he's 27 years old and could potentially net a late first-round or multiple second-round picks from a team looking to add a two-way wing to make a playoff push.

Ayton, Grant, and Thybulle seem like the obvious pieces to move, but one more complicated situation is Simons. Trading Simons goes hand in hand with the first two worst possible outcomes and should depend on how Scoot and Sharpe (when he returns) look this season.

Assuming Scoot and Sharpe make significant leaps this season, then it makes more sense to trade Simons, as the backcourt trio can't all effectively start alongside each other. The Blazers have been wise to take a "wait and see" approach surrounding Simons. If Sharpe, or more likely, Henderson, doesn't pan out as expected, Simons is a great piece to keep around long-term, as he's only 25 and can play either guard position.

But to keep Simons would likely mean they don't trust one of their guards they recently spent a top-ten pick on, which would be considered a failure.