Anfernee Simons’ Path to Stardom: A Potential Award-Winning Season with the Boston Celtics

The Boston Celtics, navigating a tumultuous 2025-26 NBA season without their cornerstone Jayson Tatum due to a torn Achilles, have placed significant faith in Anfernee Simons, acquired from the Portland Trail Blazers in a blockbuster trade for Jrue Holiday. At 26, Simons is poised to seize a larger role alongside Jaylen Brown and Derrick White, potentially catapulting him into the conversation for awards like Most Improved Player or Sixth Man of the Year. His explosive scoring, dynamic playmaking, and fit within Boston’s system make him a prime candidate for a breakout campaign. This 2,000-word analysis explores Simons’ potential for an award-winning season, delving into his skill set, the Celtics’ roster dynamics, and the unique opportunity presented by Tatum’s absence.

Simons’ Journey and Skill Set

Anfernee Simons, selected 24th overall by Portland in 2018, has evolved from a raw, athletic prospect into a polished scoring guard. In the 2024-25 season, he averaged 22.6 points, 5.5 assists, and 3.6 rebounds, shooting 38.5% from three on 8.8 attempts per game. His game is defined by electrifying athleticism, a quick first step, and a smooth shooting stroke, allowing him to score at all three levels. Simons’ ability to create off the dribble, hit pull-up jumpers, and finish above the rim has drawn comparisons to players like Jamal Murray and C.J. McCollum.

In Portland, Simons often operated in the shadow of Damian Lillard or shared ball-handling duties with Scoot Henderson, limiting his ability to showcase his full potential. His move to Boston, a perennial contender with a championship pedigree, offers a new stage. The Celtics’ up-tempo, spacing-heavy system under coach Joe Mazzulla aligns perfectly with Simons’ strengths, setting the stage for a career-defining season.

The Celtics’ Roster Overhaul and Simons’ Opportunity

The 2025 offseason was a turning point for the Celtics. Tatum’s Achilles injury, sustained during a second-round playoff loss in 2025, forced president of basketball operations Brad Stevens to make drastic moves to stay under the NBA’s second tax apron. Trading Kristaps Porzingis to Atlanta and Jrue Holiday to Portland for Simons, while letting Al Horford and Luke Kornet depart in free agency, reshaped the roster. The current lineup, featuring Jaylen Brown, Derrick White, Payton Pritchard, and Simons, supplemented by role players like Sam Hauser, Luka Garza, and Josh Minott, is competitive but lacks the star power of the 2024 championship team.

Tatum’s absence leaves a gaping hole in Boston’s offense, as he averaged 30.1 points per game in 2024-25. Jaylen Brown, now the team’s primary option, is a dynamic scorer but thrives most when paired with a secondary creator. Simons, with his ability to initiate offense and create his own shot, fills this void. His role as either a starter or high-usage sixth man positions him to post career-high numbers, potentially elevating him to All-Star consideration or individual awards.

Why Simons is Primed for a Breakout

Expanded Role and Usage

In Portland, Simons’ usage rate hovered around 28%, reflecting his role as a secondary or co-primary option. In Boston, with Tatum sidelined, his usage could climb to 30-32%, placing him among the league’s top offensive engines. The Celtics’ system, which led the NBA in offensive rating in 2024, emphasizes three-point volume and drive-and-kick plays, areas where Simons excels. His ability to run pick-and-rolls, attack closeouts, and knock down catch-and-shoot threes makes him a seamless fit.

Simons’ scoring versatility allows him to exploit mismatches, whether through step-back threes or explosive drives. In a system that encourages pace and space, he could average 25-27 points and 6-7 assists per game, numbers that would rival top guards like De’Aaron Fox or Tyrese Maxey. Such a leap would not only boost Boston’s playoff hopes but also make Simons a strong candidate for individual honors.

Most Improved Player Candidacy

The Most Improved Player (MIP) award often goes to young players who capitalize on increased opportunity or a change in environment. Simons fits this mold perfectly. Recent winners like Tyrese Maxey (2024) and Lauri Markkanen (2023) thrived after stepping into larger roles on competitive teams. Simons’ move to Boston, coupled with Tatum’s absence, gives him a platform to showcase his growth.

If Simons boosts his scoring to 25+ points per game while maintaining his 38-40% three-point shooting, he could lead the MIP race. His playmaking, which improved to 5.5 assists per game in 2024-25, could also take a step forward in Boston’s ball-movement-heavy system. A season averaging 26 points, 6.5 assists, and 4 rebounds on efficient shooting would make him a compelling case, especially if the Celtics remain a top-four seed in the East.

Sixth Man of the Year Potential

If Mazzulla opts to start White and Pritchard alongside Brown, Simons could thrive as a sixth man, leading Boston’s second unit with instant offense. His scoring prowess mirrors that of past Sixth Man of the Year winners like Jordan Clarkson (2021) and Malik Monk (2024 runner-up). Simons’ ability to dominate bench units with pull-up threes and transition buckets makes him a natural fit for this role.

A season averaging 20-22 points off the bench, with 40% field goal shooting and 38% from three, would put Simons in the award conversation. His playmaking would also elevate teammates like Garza and Minott, creating a dynamic second unit. The Celtics’ depth allows Simons to focus on scoring in this role, maximizing his impact in 25-30 minutes per game.

Fit Within Mazzulla’s System

Boston’s offense thrives on versatility, spacing, and pace, all of which play to Simons’ strengths. His 38.5% three-point shooting on high volume adds a critical dimension, especially with Porzingis’ departure reducing frontcourt spacing. Simons’ ability to push the ball in transition, a staple of Mazzulla’s system, creates easy scoring opportunities. His experience running pick-and-rolls in Portland pairs well with bigs like Garza, who can roll to the rim, or Hauser, who can pop for threes.

Defensively, Simons is not elite, but he’s shown progress. At 6-foot-3 with a 6-foot-9 wingspan, he has the tools to be a pesky defender, particularly in Mazzulla’s aggressive schemes. Playing alongside White, a First-Team All-Defensive guard, and Brown, a capable wing defender, will mask Simons’ weaknesses, allowing him to focus on offense. His defensive effort, which improved in Portland, will be critical to earning Mazzulla’s trust.

Challenges to Overcome

Simons faces several hurdles in achieving an award-winning season. First, adapting to Boston’s high-pressure environment will be a test. In Portland, he played for a rebuilding team with little scrutiny; in Boston, every game carries playoff weight. Handling the expectations of a fanbase accustomed to titles will be crucial.

Second, Simons’ defense remains a work in progress. Elite Eastern Conference guards like Jalen Brunson, Donovan Mitchell, and Tyrese Haliburton will test him. Improving his point-of-attack defense and staying engaged off the ball will determine whether he earns starter-level minutes or settles into a bench role.

Finally, Simons’ contract situation adds uncertainty. In the final year of a four-year, $100 million deal, he’ll be an unrestricted free agent in 2026. A breakout season could price him out of Boston’s budget, especially with the team hovering near the second apron. Balancing his role with long-term financial considerations will be a challenge for Stevens and the front office.

Comparisons to Breakout Stars

Simons’ trajectory resembles that of players who leveraged new opportunities to achieve stardom. Tyrese Maxey’s 2024 MIP campaign saw him average 25.9 points and 6.2 assists after James Harden’s departure from Philadelphia. Similarly, Jamal Murray’s breakout in Denver’s 2020 playoff run showcased his ability to perform on a big stage. Simons, like Maxey and Murray, is a young guard with untapped potential stepping into a high-profile role on a contender.

Boston’s winning culture amplifies Simons’ opportunity. Unlike Portland, where playoff appearances were rare, the Celtics offer a platform to shine in meaningful games. If Simons embraces this environment, he could emulate the paths of Maxey and Murray, becoming a household name and an award contender.

Broader Implications for the Celtics

A breakout season from Simons would have far-reaching implications. With Tatum expected to return in 2026-27, a core of Tatum, Brown, Simons, and White could rival any in the East, especially if Simons develops into a 25-point scorer. His emergence would also reduce the need to pursue risky signings like Damian Lillard, Ben Simmons, or Russell Westbrook, as rumored. A cost-effective star would allow Boston to maintain flexibility under the second apron while building a sustainable contender.

Simons’ success could also stabilize the roster. The trades of Porzingis and Holiday weakened Boston’s depth, and a thin frontcourt remains a concern. If Simons emerges as a reliable second or third option, the Celtics can focus on adding complementary pieces, such as Pascal Siakam or Walker Kessler, via trade or free agency.

The Role of Rivalry and Team Dynamics

The Celtics’ rivalry with teams like the Philadelphia 76ers and New York Knicks adds pressure to Simons’ role. Outperforming guards like Maxey and Brunson in head-to-head matchups could boost his award candidacy and cement his status as a rising star. Additionally, his chemistry with Brown and White will be critical. Brown’s leadership and White’s defensive prowess create a supportive environment, but Simons must prove he can handle the spotlight.

Anfernee Simons is on the cusp of an award-winning season with the Boston Celtics in 2025-26. His scoring prowess, three-point shooting, and playmaking align seamlessly with Joe Mazzulla’s system, and Jayson Tatum’s absence provides a golden opportunity to shine. Whether as a starter averaging 25+ points or a sixth man providing instant offense, Simons has the tools to contend for Most Improved Player or Sixth Man of the Year. Challenges like defensive improvement and contract uncertainty loom, but his fit alongside Jaylen Brown and Derrick White, combined with Boston’s championship culture, sets the stage for a breakout. If Simons capitalizes on this moment, he could not only earn individual accolades but also help the Celtics remain a playoff force, laying the foundation for a new era of success in Boston.