Blazers must trade Anfernee Simons immediately after missing ideal window

The longer they wait, the worse it gets.
Memphis Grizzlies v Portland Trail Blazers
Memphis Grizzlies v Portland Trail Blazers | Soobum Im/GettyImages

Last season was the Portland Trail Blazers’ golden window to trade Anfernee Simons, and GM Joe Cronin missed it. Now, he needs to act fast to maximize whatever trade value remains.

Just last offseason, Simons was named one of the top ten trade assets on the market. Teams would have lined up to land a prolific 24-year-old guard coming off his best statistical season, averaging a career-high 22.6 points and 5.5 assists while shooting 38.5 percent from beyond the arc. Now, not so much.

By his standards, Simons is coming off a relatively down year in which he averaged 19.3 points, 4.8 assists, and 2.7 rebounds on 43/36/90 shooting splits. But his play isn't the main factor -- it's more about the timing of it all.

Why the Blazers must move on from Anfernee Simons ASAP

For one, there is a lot more competition in terms of potential trade candidates this summer. ESPN's Shams Charania predicted that this could be the craziest offseason ever. Even Simons' obvious landing spot, the Orlando Magic, should be viewing him as a backup plan if trades for better players like Darius Garland, among others, don't materialize.

Declining play and market competition will make it more challenging for the Blazers to get a significant haul from Simons. However, the most critical factor in Simons' decreased trade value compared to last summer is that the team trading for him will have to extend him.

Simons actually fits into the Blazers' young core as he's similar in age to their building blocks, Deni Avdija and Toumani Camara. He also provides floor spacing and secondary playmaking, two areas that Portland still needs to address. But, on top of giving Scoot Henderson the keys to the backcourt, another reason to move on from him is that his next extension won't be worth it relative to his impact on winning as an undersized offensive-minded guard who isn't a true table-setter.

With the new CBA, teams must be highly selective with who they are dishing out these massive contracts. And the harsh reality is that it will be disadvantageous to extend Simons because you can't build a contender around him being one of your top-paid players.

The problem is that other teams around the league know this, too.

Orlando is a perfect trade partner because their desperation for shooting and backcourt help outweighs any concerns surrounding his next contract. But with each passing day that Simons gets closer to the end of his contract, he loses value. No team should want to trade for Simons as a rental, and it will be hard to convince them to give up significant assets on top of his impending extension.

That's why Cronin needs to do something he rarely does -- lower his asking price and move Simons immediately. The longer he waits, the harder it'll be to get anything meaningful in return.