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Dec 28, 2024; Portland, Oregon, USA; Dallas Mavericks guard Kyrie Irving (11) drives to the basket during the second half against Portland Trail Blazers guard Anfernee Simons (1) at Moda Center. Mandatory Credit: Troy Wayrynen-Imagn Images Troy Wayrynen-Imagn Images

Celtics Insider Provides Update on $100 Million Guard Trade Rumors

Originally posted on Boston Celtics on SI | By Jason Fray | Last updated Aug 26, 2025 1:00 PM ET

When the Boston Celtics traded Jrue Holiday to the Portland Trail Blazers earlier this summer, the move was done primarily to open up cap flexibility in years to come.

Promising young guard Anfernee Simons came back to Boston in the deal. He's a guy that can score 20+ points on any given night with enough usage. Some have questioned whether he's a starting guard on a good team — or rather a potentially excellent scoring option off the bench.

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Simons will be a free agent at the end of the year which makes his status in Boston interesting. The Celtics could opt to hold onto him for the sake of winning.

The franchise also could deal him before the trade deadline as a way to get something for Simons as opposed to seeing him leave in free agency (barring an unlikely extension).

Not sure I see much of a path to a Simons deal for PHI/MIL/DEN.

Sixers could S&T Grimes but that would be difficult for various reasons. Bucks could trade Portis or Kuzma, but don’t see that either. I don’t see a path for the Nuggets at all unless they get hurt later.
— Bobby Manning (@RealBobManning) August 24, 2025

Celtics reporter Bobby Manning is highly dialed in to the musings surrounding the franchise. He took to X and surmised that possible Simons deal involving the Philadelphia 76ers, Milwaukee Bucks, and Denver Nuggets may be too difficult to pull off.

As Manning mentions, a sign-and-trade involving Quentin Grimes doesn't appear to be in the cards. Milwaukee could offer Kyle Kuzma or Bobby Portis Jr. However, both appear to be major pieces for the Bucks this season.

The best bet for the C’s, in my opinion, has always been carrying Simons into the season and seeing where it goes. Brooklyn, Utah could make something happen, but it would cost C’s valuable draft capital they don’t want to part with. They only have 4 seconds left, by the way.
— Bobby Manning (@RealBobManning) August 24, 2025

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Manning suggests that Boston keep Simons and assess from there. There's a world where the Celtics might not be very good — yet Simons has exploded in a contract year. If his value does increase, there could be multiple pathways for the Celtics to garner young players and/or draft capital.

What Will Boston's Front Office Do with Simons?

The latter is likely what the front office is pursuing. The thought of taking on a player with a longer deal likely defeats the purpose in trading Holiday in the first place unless the acquisition can be a fit alongside the current core.

In all likeihood, Simons will get a decent amount of minutes as a member of the rotation. Whether he starts or not is also up for debate. Derrick White is essentially a shoe-in to start at one of the guard spots. Depending on what Boston wants to do, Simons could start next to White and Jaylen Brown — though reigning Sixth Man of the Year Payton Pritchard figures to also be heavily in the mix.