The Portland Trail Blazers have an 18-29 record, the seventh worst in the association. They've played much better basketball as of late, winning five of their last six games. It's been entertaining watching things finally click for their young roster. But at the same time, one can't help but wonder if all this winning is doing more harm than good in the long run.
Portland would be better off going through more growing pains to help their young core develop while also increasing their odds of landing a top pick. That's something that GM Joe Cronin must prioritize in general leading up to the February 6 trade deadline. However, more specific factors with individual trade pieces also need to be considered.
1. Jerami Grant's massive contract
The Blazers signed Grant to a substantial five-year, $160 million deal on the first day of free agency in 2023, just one day before Damian Lillard's trade request. The contract was agreed upon but not yet formalized and signed; however, Lillard's request didn't alter Portland's intentions to proceed with Grant's deal.
It's fair to wonder whether the Blazers actually wanted to go through with Grant's contract after finding out about Lillard, but as Sam Quinn of CBS Sports noted, "Teams don't rescind agreements in the moratorium period. It would ruin their league-wide credibility. No team would cross Rich Paul like that."
The Grant contract was head-scratching at the time, but Portland finally had a chance to get out of it this summer. Yet Cronin was reportedly asking for two first-round picks for someone who was owed $160 million. Obviously, a deal never materialized, as that was too steep of an asking price.
Now, the Blazers need to essentially take whatever they can get. If they don't, that contract will become a major headache.
Grant has a player option in 2027-28. That's far enough away to overlap with the Blazers' young core finally making a playoff push. Portland won't be able to upgrade their roster when it matters most.
2. Robert Williams III's injury history
Robert Williams III has been playing well this year, and it's been incredible to see him back to the impactful level of player he was in Boston. However, the risk outweighs the reward for the Blazers to keep him around past the deadline. He's only played more than 35 games in two seasons throughout his career.
It would be one thing if Portland were ready to contend immediately, but the Blazers are years away from that being the case. It could be challenging to align the timelines so Williams is still healthy while the Blazers are ready to play winning basketball.
We love Williams as a player, and it's easy to see why other teams would want him despite his injury history. But the Blazers need to cash in their chips at this point in their rebuild.
3. Anfernee Simons' next deal
Portland's backcourt has been the most frustrating situation all season. Now, the Blazers are playing big with Anfernee Simons as the only true guard in the starting lineup. To Chauncey Billups' credit, it's been incredibly effective, especially on the defensive end. But Cronin needs to make a trade to sort out this mess, and the easiest way to solve their logjam is to trade Simons.
Sharpe and Henderson have both shown enough flashes to feel comfortable making the long-term switch. And in the short term, the Blazers need to lose more games anyway.
Portland also needs to be proactive with Simons' contract. He's owed $25.9 million this season and $27.7 million next season. That's reasonable for now, but he will likely cost north of $30 million annually in his next deal. Do the Blazers want to lock him long-term for that amount?
He's great, but your ceiling is much lower if he's one of your team's best (and highest-paid) players. The Indiana Pacers have a similar dilemma with Myles Turner, who arguably impacts winning at a higher level than Simons with his rim protection and floor spacing.
Paying a high-volume combo guard that amount of money isn't the right move, especially considering who is behind him in the depth chart.