The Portland Trail Blazers are currently in the worst position a team could be in. Despite finishing with the worst record in the Western Conference at 21-61, they still found a way to be in the luxury tax and first apron heading into the 2024-25 season. The Blazers need to make a trade for the sake of finances and the team's roster in general.
They are currently in a unique spot from a financial standpoint. Deandre Ayton, Anfernee Simons, Jerami Grant, and Malcolm Brogdon combine for 80 percent of the Trail Blazers' salary cap. Having so much money invested into a handful of players yet being far from competing in the playoffs is certainly not ideal.
But, with the progression of their up-and-coming prospects and the addition of two lottery picks, there is reason for optimism surrounding their rebuilding process. Moving these key five players can help Rip City as they continue their roster overhaul.
1. Deandre Ayton
It's difficult to gauge how much Deandre Ayton contributes to a team. He can put up excellent stats that are somewhat "empty" and don't impact winning as much as you'd expect if you just saw the box score. The NBA style of play has transitioned away from centers like Ayton - someone with an excellent midrange game that can't shoot threes and isn't a defensive-minded rim protector.
To be fair, Ayton is an above-average starting center in the NBA. He turned his play around towards the end of the season after strangely blaming his slow start in Portland for having to sleep on an air mattress. Post All-Star break, Ayton averaged 22.7 points and 12.5 rebounds, showing flashes of what made him the No. 1 overall pick in the 2018 NBA Draft.
The issue with Ayton is that we will always wonder if he will consistently be able to do that throughout an entire season. Combine that with the fact that his play style isn't ideal in today's NBA, and it's hard to justify paying Ayton; Portland owes him $34 million next season and $35.5 million the following season. Paying a center that doesn't protect the paint on defense or space the floor on offense that amount of money limits your team's upside, financially and in terms of play style.
It could make sense to part ways with Ayton and take advantage of his high stock right now following his strong finish to the season. Portland could replace Ayton in this year's draft with a center like Connecticut's Donovan Clingan and the return of a hopefully healthy Robert Williams, allowing them to address other positional needs while saving cap room.
2. Anfernee Simons
Blazers fans seem divided about what they'd like the team to do with Simons. Besides playing remarkably similar to arguably the greatest Blazers player of all time, Damian Lillard, there are valid reasons for wanting to keep Simons around. For one, he's still only 24 years old and will be entering his prime by the time the Blazers hopefully reap the benefits of their rebuilding process. He's also the team's best shooter, an area they desperately need help in.
On the surface, it doesn't make much sense to get rid of a 24-year-old guard who just averaged 22.6 points and 5.5 assists while shooting 38.5 percent from three. However, the problem isn't necessarily with Simons. It's simply about the Blazers' roster construction, which could cause Simons to be the odd man out.
The Blazers plan on having former No. 3 overall pick Scoot Henderson as their franchise point guard, despite his relatively shaky start to his NBA career in his rookie season. Although a great shooter, Simons is a giant defensive liability due to his 6-foot-3, 193-pound frame. Henderson is also 6-foot-3, meaning that backcourt can't coexist effectively long-term, at least from a defensive standpoint.
With the amount of physicality in the playoffs and the NBA superstars who are so well-versed in taking advantage of size mismatches, the Blazers' best option in the long term may be to get rid of one of their best players.
Per Sean Highkin of the Rose Garden Report, Simons wants to have the opportunity to win soon. Simons has been great for Portland, but both parties may benefit from a change of scenery.
3. Jerami Grant
The Blazers never should have signed Jerami Grant to his five-year, $160 million contract last summer. This offseason is an opportunity for a fresh start as they focus on clearing cap space. It would also open up more playing time for their younger players, including forwards Jabari Walker and Toumani Camara.
Moving Grant may be the most challenging of the five players mentioned, with questions surrounding whether he is a positive or negative trade asset due to the size of his contract. Grant's salary may limit the number of teams that would be willing to take him on - it would likely have to go to a team looking to add another piece to get over the playoff hump. They would need cap space or a salary filler they can trade with fewer years remaining on their contract than Grant.
Like Simons, Grant is one of the team's best shooters. Even if you are a rebuilding team, it's always tough to trade someone who is arguably your best player, nonetheless someone who plays a position of need. Still, Grant is 30 years old and doesn't fit their rebuilding timeline. While a great NBA player, he's not a star who can move the needle for Portland anytime soon.
The Blazers want to keep their cap flexibility open in the coming years, and dumping Grant's salary would be a great start.
4. Malcolm Brogdon
Malcolm Brogdon is currently involved in numerous trade rumors. Brogdon's injuries limited him to only 39 games this season with the Blazers, but he was productive on the court. Brogdon averaged 15.7 points, 5.5 assists, and 3.8 rebounds per game.
There are multiple reasons to keep Brogdon around. For one, he's reportedly happy to be in Portland.
He's also a solid veteran presence and could particularly help the Blazers' young backcourt develop. Lastly, Brogdon helps fill the Blazers' biggest offseason need as a shooter—he was the most efficient three-point shooter on the team at 41.2 percent. But the reasons to part ways with the former Sixth Man of the Year outweigh the reasons to keep him around.
The Blazers' point guard situation is already too crowded, and trading Brogdon will give their young guards more opportunities to get playing experience. Brogdon doesn't fit in with the Blazers timeline at 31 years old, not to mention he is often injured. Brogdon has only eclipsed 60 games in his eight-year career in three seasons.
With Brogdon's contract expiring, this may be the best time to move the Blazers guard. He was also heavily involved in trade rumors at last year's deadline. He is already piquing interest from teams around the league. Practically every team could use a veteran point guard who can come in and orchestrate the offense within the game's flow while spacing the floor for star players to operate.
Brogdon is an underrated player who would be an excellent addition to any team he plays for. However, he doesn't fit the Blazers' direction or positional need.
5. Matisse Thybulle
The Blazers matched the Mavericks' offer sheet for Thybulle last summer, which was a three-year, $33 million deal. Like Brogdon, there are also a few reasons for the Blazers to keep Thybulle around.
Thybulle is only now entering his prime at 27 years old. He fits in with the Blazers' rebuilding timeline as someone who could be a veteran piece by the time their young core develops. He also fills a need for Portland as a two-way wing. Thybulle is a two-time All-Defensive Second-Team forward. He's improved his shooting throughout his career and isn't quite the liability he once was. Thybulle connected on 34.6 percent from three this season.
However, teams would likely be willing to trade a somewhat significant asset, such as a late first-round pick or multiple second-round picks, to obtain Thybulle. He is the type of player playoff teams want to add as someone who can make life difficult for the other ball-dominant wing superstars like Jayson Tatum or Luka Doncic. He's also on an extremely reasonable contract.
With the Blazers emphasizing patience in their rebuild, it still makes sense to be open to trading Thybulle in exchange for more draft compensation. Especially now that they have another version of Thybulle in rookie Toumani Camara.