The Boston Celtics are still working the phones this offseason, with one player at the center of it all: Anfernee Simons.
Boston landed Simons in the Jrue Holiday trade, but reports have consistently suggested the Celtics are looking to flip him as part of their effort to reduce payroll. The 25-year-old guard is owed $27.6 million for the 2025–26 season, making him more of a financial hurdle than a long-term building block in Boston.
Now, a familiar rival may be emerging as a possible landing spot.
Bucks Linked to Anfernee Simons
Photo by Maddie Meyer/Getty ImagesAnfernee Simons, Boston Celtics
According to Sam Amico of Hoops Wire, the Milwaukee Bucks have been “contemplating” a trade for Simons. The fit makes sense — Milwaukee recently stretched and waived Damian Lillard, leaving a glaring hole in their backcourt.
Simons, who averaged 19.3 points, 2.7 rebounds, and 4.8 assists last season, could provide an instant scoring boost and give the Bucks a reliable perimeter creator. For Boston, moving his contract would take them another step closer to avoiding heavy tax penalties.
At this stage, it’s unclear what type of return the Celtics could get from Milwaukee, or whether draft capital would need to be included to make a deal work.
Mock Trade Pitch: Celtics and Bucks
Boston Celtics receive:
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Bobby Portis ($14.5M, signed through 2027 with 2027–28 player option)
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Gary Trent Jr. ($3.7M)
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Ryan Rollins ($4M)
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2026 second-round pick (via MIL)
Milwaukee Bucks receive:
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Anfernee Simons ($25.3M)
Why Boston does it: They move off Simons’ $27.6 million salary for the 2025–26 season without attaching a first-round pick, which has been their priority all offseason. Instead of one big cap hit, they split it into multiple mid-sized contracts that are easier to move. This improves flexibility and avoids unnecessary strain as the franchise prepares for Jayson Tatum’s eventual return.
On the court, Portis provides toughness and rebounding on a steady deal that runs through 2027. Trent Jr. adds perimeter shooting. Rollins is a developmental guard who could benefit from Boston’s system. Compared to Simons, the incoming salaries are more manageable. They give the Celtics both immediate depth and future roster options.
Why Milwaukee does it: The Bucks land the best player in the deal, filling the scoring void left by Damian Lillard. At just 25 years old, Simons provides perimeter creation that can take pressure off Giannis Antetokounmpo and gives Milwaukee a long-term guard option.
Parting with Portis is painful given his role as a sixth man and fan favorite, but Simons represents the type of young, high-upside talent that could extend Milwaukee’s window. Depth takes a hit, but the payoff is landing a guard who fits both the present and the future.
Timing matters here, too — because Portis cannot be traded until December 15, 2025, a deal like this would have to happen closer to the February trade deadline rather than in the offseason.
Celtics Face a Tough Choice
The Celtics have already made major changes to their roster this summer, including parting ways with multiple starters. With Jayson Tatum sidelined until 2026–27, Boston’s path forward is complicated.
Trading Simons would clear salary and align with a more patient approach, but it would also mean punting on the chance to see him fit alongside Jaylen Brown in the short term. If the Celtics are serious about contending this season, moving Simons could cut into their depth at guard.
Still, given Boston’s financial situation, it seems more likely the team will prioritize flexibility over a one-year push.
What Comes Next
The Celtics don’t appear eager to attach additional draft picks in any Simons deal. That may be the price of doing business. Rival teams know Boston wants to shed salary. Leverage could become an issue.
For now, the Bucks are one of the first concrete teams linked to Simons. They likely won’t be the last. Simons doesn’t appear to be part of Boston’s long-term plans, so moving him before he reaches free agency in 2026 could be a practical step for a franchise in transition. Boston’s decision will say a lot — are they focused on surviving the upcoming season, or reloading for Tatum’s return?
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