Even before being eliminated by the New York Knicks, Boston Celtics fans had a good idea that Jrue Holiday would be traded in the offseason. At the same time, no one expected the Celtics to get Anfernee Simons in return from the Portland Trail Blazers.
Simons was the Trail Blazers’ best player the past two seasons, averaging 20.6 points, 5.1 assists, and 3.1 rebounds in that span. Although he’s coming off a down season, he still managed to drill 36.3% of his threes on 8.5 attempts and led the team in scoring (19.3).
Simons seems like a perfect fit for head coach Joe Mazzulla on paper. At the same time, with Jayson Tatum sidelined indefinitely and the Celtics remaining open to trading him, the ex-Blazer's tenure will likely be short-lived, which could cost him a significant amount of money in the summer.
Celtics' Anfernee Simons Will Cost Himself a Payday in 2025-26
Simons, 26, is entering the final year of his four-year, $100 million extension he signed with the Trail Blazers in 2022. It doesn’t matter what team he plays for next year; the former 2018 first-rounder will want a pay raise next summer.
As things currently stand, Simons will have to improve defensively if he wants a pay increase. He is a noted poor defender, finishing last year with a 119 defensive rating per 100 possessions (119), marking the sixth consecutive season it's reached that number or been worse.
Although he averaged a career-high 0.9 steals last season, players he guarded still shot 50.6% from the field. Having Derrick White and Jaylen Brown may take the pressure off of Simons, but he’s still got a way to go from being a solid defender.
Not only will his defense potentially cost him a payday, but his current status on the team could hurt his value. Back in August, FastBreak's Grant Afseth reported that Payton Pritchard would start over Simons. Pritchard has improved every season and took a big leap last season, ultimately taking away closing game minutes from Holiday.
This is a crucial blow to Simons, who’s been a starter the last three seasons. While Simons has been successful on the bench, no team will pay more than $100 million to a bench player, regardless of how good he is.
Although Simons is a great scorer and catches fire easily, he has a lot to prove to the Celtics (and the other 29 teams) if he wants to secure a lucrative deal in the 2026 NBA offseason.