The Boston Celtics, fresh off a 2024 NBA championship, are undergoing a seismic roster overhaul that has shocked #CelticsNation. With Jayson Tatum sidelined by a devastating Achilles injury, key championship pieces like Jrue Holiday and Kristaps Porziņģis traded, and veterans Al Horford and Luke Kornet gone, Boston is prioritizing financial flexibility over immediate contention. Now, NBA insider Jake Fischer reports the Celtics are actively shopping Anfernee Simons, the 26-year-old guard acquired in the Holiday trade, to further reshape their future. As the 2025 season looms, what does this mean for Boston’s strategy, and could a blockbuster trade redefine their path?
The Boston Celtics’ 2024-25 season was poised for a title defense until Jayson Tatum’s ruptured Achilles, suffered in a late 2024 practice, upended everything. The injury, sidelining their All-NBA star for most or all of the season, forced president Brad Stevens to rethink the franchise’s direction. Last season’s roster, which posted a 64-18 record and a +11.7 net rating (best in the NBA, per Basketball-Reference), was dismantled in months. Jrue Holiday and Kristaps Porziņģis were traded, Al Horford signed with Miami, and Luke Kornet joined Atlanta, per ESPN. In their place, Boston added budget-friendly players like Chris Boucher, Luka Garza, and Josh Minott, ducking the second tax apron ($190.1 million, per Spotrac) but still hovering near the first luxury-tax line ($170.8 million). Now, Anfernee Simons’ $27.7 million expiring contract is on the trade block, signaling a deeper reset, per Jake Fischer on the NBA Insider Notebook.
Simons, acquired in the Holiday trade, is a 26-year-old scoring guard averaging 22.6 points and 5.5 assists in 2024, with a 38.5% three-point clip on 8.8 attempts, per NBA.com. His expiring deal makes him a prime asset for contenders needing shooting, but Boston’s shift away from immediate wins makes him expendable. Fischer notes, “The Celtics are going to continue to look for salary-shedding opportunities, and they are going to listen to incoming trade calls for Anfernee Simons.” Moving his salary could save millions, reset the repeater-tax clock, and net draft picks or young talent, aligning with Stevens’ long-term vision. With Tatum out, Boston’s championship odds have plummeted from +300 to +1800, per FanDuel, trailing Eastern Conference rivals like Philadelphia (+800) and New York (+1200). This reality has pivoted the Celtics toward 2026 and beyond.
A proposed three-team trade, outlined by Bleacher Report, illustrates Boston’s strategy. The deal would send Simons to the Toronto Raptors, who ranked 29th in three-point makes (11.5 per game) in 2024, per NBA.com. Toronto would part with RJ Barrett (21.8 points, 43.7% FG in 2024), while the Brooklyn Nets facilitate, acquiring Barrett and sending Terance Mann (8.8 points, 38.7% 3P) to Boston, plus salary fillers like Dennis Schröder ($13 million). Boston could also gain Ochai Agbaji (5.8 points, 42.7% FG) and second-round picks. This trade slashes payroll by $10-15 million, per Spotrac’s projections, and adds versatile wings. Mann, 28, offers defensive flexibility (1.2 steals per game) and fits Boston’s core of Jaylen Brown (26.7 points in 2024) and Derrick White (15.2 points, 39.6% 3P), per ESPN. Agbaji, 24, brings upside as a 6’5” shooter, while picks bolster Stevens’ asset stockpile, which already includes six second-rounders through 2030, per RealGM.
Boston’s roster moves reflect a philosophical shift. Last season’s title run leaned on Holiday’s two-way play (12.5 points, 4.8 assists) and Porziņģis’ spacing (20.1 points, 51.6% FG), per Basketball-Reference. Their trades, netting Simons, Boucher (6.1 points, 4.5 rebounds), Garza (4.0 points, 54.0% FG), and Minott (2.7 points), prioritized cost control over star power. Horford’s departure (8.6 points, 6.4 rebounds) and Kornet’s exit (5.3 points, 4.1 rebounds) further cut costs but weakened depth. The Celtics’ 2024-25 payroll, at $170.8 million, is $2.3 million below the first tax line, but Simons’ salary pushes them close to penalties. Trading him could save $20 million in taxes and reset the repeater clock, critical for a franchise facing luxury-tax restrictions through 2028, per Spotrac. Stevens’ prior trades, like acquiring White in 2022 for a first-rounder, show his knack for balancing present and future, per The Athletic.
The trade’s appeal extends beyond finances. Mann’s 6’5” frame and 3-and-D skill set (1.1 blocks per game in spot starts) complement Brown and White, who combined for 5.1 assists and 41.2% three-point shooting in 2024, per NBA.com. Agbaji, a 2022 lottery pick, offers developmental potential, shooting 35.5% from three in limited minutes. Toronto benefits from Simons’ scoring, addressing their 28th-ranked offensive rating (112.1), while Brooklyn’s rebuild gains Barrett (23 years old, $25.6 million deal), per Bleacher Report. X posts, like @CelticsInsider’s “Simons trade could set us up for 2026,” reflect fan optimism, though some, like @NBATalk’s “Why trade Simons when he’s our best scorer without Tatum?” question the move. Without Tatum, Boston’s offense, 2nd in 2024 (120.6 rating), may dip, with Brown projected to carry 30+ points per game, per ESPN’s Kevin Pelton.
The Celtics’ reset isn’t without risks. Trading Simons could weaken a backcourt already thin without Holiday, with Payton Pritchard (9.6 points, 44.0% 3P) and rookie Baylor Scheierman (39.8% 3P in college) unproven as starters, per NBA Draft Digest. Boston’s defense, 2nd in 2024 (110.6 rating), may falter without Holiday and Horford, though White’s 1.2 steals and Mann’s versatility could mitigate losses. The Eastern Conference, with Philadelphia’s Joel Embiid (34.7 points) and New York’s Jalen Brunson (28.7 points), poses a challenge, per NBA.com. A 2025 tank could secure a top-10 pick in a loaded draft, featuring Cooper Flagg (projected No. 1, 18.2 points in high school), per ESPN, but risks fan backlash, as seen in @CelticsNation’s “No tanking after a title!” posts. Stevens’ focus on 2026, when Tatum returns and Brown’s $57 million cap hit peaks, suggests a long game.
Alternative trade scenarios exist. The Los Angeles Lakers, seeking guard depth, could offer Gabe Vincent ($11 million) and a 2027 first-rounder, per HoopsHype. The Miami Heat, with $172 million in payroll, might propose Duncan Robinson (14.1 points, 37.9% 3P) and picks, per The Ringer. These deals maintain Boston’s flexibility while adding assets, though none match Simons’ scoring punch. Stevens’ history—trading Marcus Smart for Porziņģis in 2023—shows bold moves pay off, per CBS Sports. With 41 wins projected by ESPN’s Basketball Power Index, Boston risks a play-in spot, but a Simons trade could prioritize youth and picks, setting up a 2026 core of Tatum, Brown, White, Mann, and Agbaji, with cap space for a max free agent like Devin Booker (+2500 to join, per FanDuel).
The Celtics’ roster overhaul, driven by Tatum’s injury and Stevens’ vision, marks a daring pivot from title contention to future flexibility. Trading Anfernee Simons could unlock draft picks, young talent like Terance Mann, and millions in savings, positioning Boston for a 2026 resurgence. But with risks of a weakened roster and fan unrest, can Stevens balance short-term pain for long-term gain?