The Boston Celtics are no strangers to the NBA’s high-stakes chess game, and their latest move—acquiring guard Anfernee Simons in the blockbuster Jrue Holiday trade—has sparked a fresh wave of intrigue. With the 2025-26 season looming, Simons, a 26-year-old sharpshooter on an expiring $25.9 million deal, finds himself at the heart of trade rumors, as reported by Clutch Points insider Brett Siegel. The Holiday trade slashed Boston’s payroll, dodging the NBA’s punitive second apron ($190.7M), but Simons’ name keeps surfacing in talks with multiple teams, hinting at further roster tweaks. With Jayson Tatum sidelined for the season due to an Achilles tear, Simons’ elite shooting and shot-creation could be a lifeline—or a trade chip to reshape the Celtics’ title chase. Can Boston harness his offensive firepower, or will they cash in on his value before his contract year ends? Let’s break down the rumors, Simons’ fit, and what’s next for the green.
Mar 21, 2025; Portland, Oregon, USA; Portland Trail Blazers guard Anfernee Simons (1) watches teammates warm up before a game against the Denver Nuggets at Moda Center. Mandatory Credit: Troy Wayrynen-Imagn Images
1. The Jrue Holiday Trade: A Financial and Strategic Pivot
The Celtics’ decision to trade Jrue Holiday, a defensive stalwart signed to a four-year, $134.4 million deal through 2028, for Anfernee Simons was a masterstroke of financial engineering. Holiday’s $33.6 million annual cap hit pushed Boston dangerously close to the NBA’s second apron ($190.7M), which triggers harsh penalties like frozen draft picks and restricted signings. Simons, on an expiring $25.9 million contract, saved roughly $7.7 million in 2025-26 cap space, per Spotrac, and paired with other moves (e.g., trading Derrick White), got Boston under the apron. This flexibility is crucial for a team rebuilding around Jaylen Brown (28.6 PPG last season) and Kristaps Porzingis, especially with Tatum out.
Simons, acquired from Portland, brings a different flavor: a 6’3” guard with a silky jumper, averaging 19.3 points, 4.8 assists, and 2.7 rebounds on 36.3% three-point shooting in 2024-25. His 8.5 three-point attempts per game over the last three seasons align perfectly with Boston’s three-heavy attack (42.5% of shots from deep, second in the NBA). But his expiring deal makes him a trade candidate, as Siegel reports: “The Celtics have held discussions with a few teams about Simons’ value since Summer League in July.” No deal is imminent, but the chatter signals Boston’s front office, led by Brad Stevens, is weighing options to either bolster the roster or clear more cap space. Fans on X are split: “Simons is a scoring machine—keep him!” vs. “Trade him for a defender; we’re soft without JT.”
2. Simons’ Fit: A Scoring Spark Amid Tatum’s Absence
With Tatum sidelined until at least April 2026, Boston needs offensive juice, and Simons delivers. His 2024-25 stats (19.3 PPG, 43.0% FG, 36.3% 3PT) showcase a dynamic shot-creator who thrives in pick-and-rolls and pull-up jumpers. In Portland, he shouldered a heavy load, averaging 3.4 made threes per game, a skill that slots seamlessly into Joe Mazzulla’s system, which saw the Celtics attempt 50.3 threes per game in 2024-25 (league-high). His ability to create off the dribble—evidenced by 4.8 assists and a 2.1 assist-to-turnover ratio—could ease pressure on Brown, who’ll face double-teams without Tatum’s gravity.
However, Simons’ defense is a glaring weakness. At 185 pounds, he struggles against bigger guards, posting a 121 defensive rating last season (bottom 10% league-wide, per NBA Advanced Stats). Boston’s switch-heavy scheme, anchored by Al Horford and Porzingis, can mask some flaws, but Mazzulla’s coaching will need to spark growth in Simons, who’s only 26. His feature in the NBA’s “No Days Off” series revealed a growth mindset: “You’re always using the time to get better… being more intentional in workouts.” If Mazzulla, who turned Derrick White into a two-way stud, can unlock Simons’ defensive potential, he could be a keeper. X buzz reflects hope: “Simons at 26 can learn to defend—Joe’s got this.”
3. Trade Rumors: Why Simons Is on the Block and What’s at Stake
Siegel’s report highlights Boston’s talks with multiple teams, exploring Simons’ trade value as his contract year looms. An expiring deal is a double-edged sword: it’s attractive for teams seeking short-term talent without long-term cap hits, but it risks losing Simons for nothing in 2026 free agency. His $25.9 million salary matches well with mid-tier stars or role players, making him a prime asset for a team projected to win 45-50 games but needing a boost to contend in the East. Potential suitors like the Lakers (seeking shooters) or Heat (eyeing Tatum before his injury) could offer picks or veterans to address Boston’s defensive holes, per Clutch Points.
Trading Simons could free up cap space for 2026, when Boston aims to reload around a healthy Tatum. Spotrac projects $20M in room if Simons walks, enabling a run at a max free agent like a future Hall of Famer (as an NBA insider dubbed a “best fit” for Boston). But keeping Simons risks a one-year rental if he chases a big deal elsewhere (projected $20-25M annually based on his 3.9 win shares). The Celtics’ 2024 title and 61-win 2025 season set a high bar; without Tatum, they’re a 4-6 seed at best. A trade could net a defensive wing or backup big, but losing Simons’ shooting in a three-centric system is a gamble. An X user summed it up: “Trade Simons for a rim protector, or we’re stuck with offense and no D.”
4. The Bigger Picture: Simons, the Celtics, and the NBA’s Financial Game
Simons’ situation reflects the NBA’s new reality under the 2023 CBA. The second apron ($190.7M) forces champions like Boston to make painful cuts—Holiday and White were cap casualties, not performance ones. Simons’ expiring deal gives Stevens leverage to either flip him for assets or keep him as a bridge to 2026, when Tatum’s return could reset the title window. His “No Days Off” ethos—emphasizing intentional workouts—signals a player hungry for a breakout, which could raise his value midseason (e.g., 20+ PPG could fetch a first-round pick).
The East is a gauntlet, with Milwaukee (Giannis’ return), Philadelphia (Embiid-Paul George duo), and New York (Brunson’s rise) loading up. Boston’s 42.5% three-point attempt rate demands shooters like Simons, but his defensive lapses (1.2 steals but weak on-ball) clash with the gritty identity of past title teams. League-wide, expiring contracts are trade gold—60% of such deals moved at the 2025 deadline, per ESPN. If Simons posts 20 PPG early, his trade value could spike, but a breakout could also convince Boston to extend him. Fans debate on X: “Simons is our mini-Dame—pay him!” vs. “Trade him before he walks for free.”
Anfernee Simons’ place in the Celtics’ rumor mill is a microcosm of Boston’s high-wire act: balancing cap relief, roster needs, and a title chase without Jayson Tatum. His sharpshooting and shot-creation are tailor-made for Mazzulla’s system, but trade talks signal Boston’s readiness to pivot for defense or future flexibility. At 26, Simons’ “No Days Off” mindset could make him a cornerstone or a valuable chip by the February deadline. Will the Celtics ride his scoring to a playoff push, or cash in for a missing piece?