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3 Big Questions for Anfernee Simons Heading Into the Boston Celtics 2025 Season

Today, as part of the "3 questions" mini-series, we're looking at Boston Celtics' guard Anfernee Simons.

Adam Taylor 19 September 2025 / 6 min read The Green Room
3 Big Questions for Anfernee Simons Heading Into the Boston Celtics 2025 Season

We're continuing with our "3 Questions" series. Today, we're looking at Anfernee Simons.

Let's get it!

Will Simons be shipped out before the trade deadline?

This is – or should be – the question on every Celtics fan's lips. Simons was added to the rotation as part of the deal that sent Jrue Holiday back to the Portland Trail Blazers. Therefore, how the Celtics handle the next 12 months of Simons' (expiring) contract will likely impact how we view the overall return for Holiday.

Simons will earn $27.6 million this season. I'd argue that's an overpay considering his defensive limitations and non-star reputation around the NBA. Simons is a very talented scorer. He is not, at least yet, an All-Star. However, his presence will eat 17.9% of the Celtics cap space this season.

To make matters worse, his expiring deal means opposing teams will look for a cut-price deal. It's not easy to find value when moving an expiring contract worth nearly $30 million per year. Therefore, the smart play might be to keep him around.

However...

If Brad Stevens does choose to stick with Simons, the smart move would be to sign him to another contract. Not because he projects to be a key piece of the next championship core – I mean, he could, we need to see how things look in action – but because it negates the risk of him walking away next summer with nothing heading back to Boston in return.

One thing I did want to do, though, is examine some of the benefits of keeping Simons around, at least for now. So, allow me to outline them quickly.

  • He's a proven three-level scorer at the NBA level
  • Has experience leading an offense in Portland
  • Knows how to deal with being the focal point of a defensive scouting report
  • Will thrive with the additional attention Jaylen Brown, Derrick White and Payton Pritchard draw ... Oh, and Sam Hauser, too.
  • He is slightly below a 3:1 assist-to-turnover ratio with a high amount of touches (65.1 per game last season) – something he can scale as a secondary or tertiary playmaker with the Celtics.
  • Could still improve his defense based on scheme, system and the talent around him.

On paper, he's certainly a talent worth keeping. However, if the right opportunity arises, flipping him should be on the table.

If you are interested in what type of trade packages Boston could get for Simons, I refer to the Four Trade Ideas For Celtics To Flip Anfernee Simons we looked at the other week.

🗣 My Take: A lot will depend on what the market looks like for Simons. Stevens is unlikely to make a move for the sake of it. Instead, I expect him to approach each potential trade opportunity on merit. If nothing is out there that makes sense, then maybe Simons re-signs with Boston and is moved at a later date. Or, maybe the cap relief of letting him walk next summer will be something the front office is interested in.

For now, though, I expect Simons' tenure with the Celtics to remain fluid.

What can we expect from his offense

There's no two ways about it: Simons is a bucket.

According to Cleaning The Glass, Simons shot:

  • 62% at the rim
  • 39% in the short mid-range
  • 52% in the long mid-range
  • 37% from three (overall)
  • 38% from the corner 3

The first thing that stands out to me is the long mid-range success.

Take a look at the above clip. Simons comes off the pin down and receives the pass. His defender successfully navigates the screen by going under, getting back to the three-point line to run Simons out of his shooting motion.

Three dribbles and a step-back later, the New Orleans Pelicans have given up an additional two points. My point here is that Simons isn't likely to hunt out long two-point attempts, but he is clearly comfortable in attacking close-outs off the bounce and finding success.

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