The Portland Trail Blazers should trade Anfernee Simons this offseason because he wants to win now (subscription required). Portland is not ready to make the jump in the loaded Western Conference. They have two gigantic contracts weighing down their books and no path to adding a star. Simons has not requested a trade, but Portland should look to keep him happy for several reasons.
The 25-year-old is entering the final year of his contract and is extension-eligible. It won’t be cheap to keep him, and the Blazers do not want to risk him testing free agency. If Simons refuses an extension or is dead set on winning immediately, Portland’s only option is to trade him. The Magic are a clear landing spot and could create a win-win move.
Beyond making Simons happy and gaining financial stability, Portland also picks a lane with their backcourt. Scoot Henderson showed flashes in year two and is ready for more minutes. That isn’t possible with Simons and Shaedon Sharpe on the Blazers’ roster.
Blazers should make the smart move to trade Anfernee Simons
Portland cannot play Simons, Sharpe, and Henderson together and only have 96 minutes available in the backcourt. The easiest solution is trading one of their 6’3 guards to open up more minutes for the other. Simons is a proven 20-point-per-game scorer, who is just entering his prime. It is the perfect moment to sell high.
The Blazers would also open up more shots for Deni Avdija to prove his late-season breakout was the new norm. He averaged just under 25 points per game and had seven 30-point performances over his final 16. The trade looks like a slam dunk for Portland as he is locked up to a bargain contract. This is just one more reason to trade Simons to the highest bidder.
The Blazers are building an exciting young team and will add another lottery pick to their mix in June. Deandre Ayton is entering the final year of his contract, so Portland will have some spacing open up. They are not ready to win in the 2025-26 season, but the flip is coming. If Simons is unwilling to wait, the Trail Blazers should move on and try to maximize their remaining young pieces.
It is a crossroads offseason for the Portland Trail Blazers. Do they keep slowly rebuilding or try to make significant changes? An Anfernee Simons trade could be the start of the shift. He wants to play for a contender and should get his wish this offseason if the Blazers are wise.