Should the Blazers Keep or Yeet Anfernee Simons?

The Portland Trail Blazers’ 2021-22 season has come to an end. The summer ahead will hold plenty of decisions for the club. They put 27 difference players on the court during the regular season. Not all are still with the team, but enough are that there’s no way the Blazers could retain them all...if they even wanted to. A 27-55 record would argue against a high retention rate, but asterisks abound despite the dismal performance.

Into this question-filled swamp stride Dave Deckard and Dia Miller with their annual review of Portland’s roster. They talk about each player, then decide whether they would keep or yeet (toss) the player in the coming year. Performance, fit, age, salary, and team priorities/direction are all open for discussion.

The series starts with Portland’s most prized free agent, Anfernee Simons. He had a banner year, and is also open for other teams to bid on this summer in restricted free agency. Should the Blazers keep him, and at what cost?

Dave: So we’re back again for your favorite exercise of the entire year, keep or yeet! And we’re starting with the guy who probably had the best overall season of any of the Trail Blazers players, Anfernee Simons. He’s a restricted free agent, scoring 17 points, shooting 44% from the field and 41% from the three-point arc. That means he’s going to cost a fortune to retain this summer. Is it worth it? What’s your take?

Dia: This is my LEAST favorite exercise of the year. I’d rather run a marathon (and if you’ve listened to our podcast y’all know how much I don’t want to do that). But here we are anyway. At least we start off with one that is a no brainer in my opinion. Absolutely 100% keep Anfernee Simons. Protect that man at all costs (well, most costs. Reasonable costs). He was such an asset before he got benched for the season, and I truly think if he hadn’t, he would have been seriously in talks for Most Improved Player. His ceiling is extremely high in my opinion, and he’s reaching for It.

Dave: Reasonable costs, eh? That is the question. There’s no doubt that Simons is the closest thing to an ascending star the Blazers have. As such, he’s nearly indispensable if their vision strays beyond the next season or two. But other teams may feel that way too. It won’t shock anybody to see his offer start north of $20 million per season. If they come in at $18 million, they should count themselves lucky.

Normally, you’d shrug that off as the price of doing business. But Portland just moved on from the Damian Lillard-CJ McCollum pairing that was:

A. Not winning big. And...

B. Super expensive.

Simons’ deal won’t be as expensive as McCollum’s, but that’s still a lot of moolah invested in two score-heavy starting guards. With Josh Hart in the wings too. Do you have any concerns about re-investing in the Lillard-Simons duo?

Dia: I have definitely considered this, and I think you have to after moving someone as good as CJ. How do you justify that, but then pay Anfernee Simons? I get why that’s a conversation. Here’s my short answer— Simons is significantly younger. To me it’s much less about Dame and Simons playing side by side as It is about Simons playing a huge role as Dame eventually ages out. However, if the plan is win now (or now-ish) and the right deal comes along, you have to consider that. But I think you have to always consider the “right deal”. That being said, I don’t think there are many I’d consider worth It. I think Ant is going to be a big part of the future of this team.

Dave: Yup. I’m on the keep side for Simons, simply because the Blazers won’t be able to replace him with comparable assets at this point. They’d have to dump the whole team to generate enough cap space to make a run at other players, and anybody young and talented enough to match Simons won’t come to Portland anyway. That’s the pitfall of the kind of approach they’ve taken, and paying a huge contract to Ant without blinking is a logical endpoint to it.

Do you agree, dear readers? Weight in on Anfernee Simons in the comment section below. Should the Blazers Keep or Yeet him, and why?