Why the Boston Celtics May Miss Out on a Superstar Signing in 2025

The Boston Celtics, fresh off a championship in 2024 but reeling from a second-round playoff exit in 2025, find themselves at a crossroads as they approach the 2025-26 NBA season. The devastating loss of Jayson Tatum to a torn Achilles has forced the franchise to recalibrate, trading away key players like Kristaps Porzingis and Jrue Holiday to shed salary and stay under the second tax apron. Recent rumors have linked the Celtics to high-profile free agents, including former All-Stars like Damian Lillard, Ben Simmons, and Russell Westbrook. However, even if these rumors materialize, the Celtics may still miss out on landing a true superstar capable of elevating them back to championship contention. This article explores the reasons behind this, delving into the team’s financial constraints, roster dynamics, and the limitations of the rumored targets.

The Celtics’ Current Roster and Financial Situation

The Celtics entered the 2025 offseason with a roster that was the envy of the NBA, boasting a deep, versatile lineup led by Tatum, Jaylen Brown, Porzingis, and Holiday. However, Tatum’s season-ending Achilles injury, suffered in the 2025 playoffs, forced a dramatic shift in strategy. To avoid the punitive restrictions of the NBA’s second tax apron, the Celtics traded Porzingis to the Atlanta Hawks and Holiday to the Portland Trail Blazers for Anfernee Simons, while also allowing Al Horford and Luke Kornet to walk in free agency. These moves created financial flexibility but left the roster thinner, with Jaylen Brown, Derrick White, and Payton Pritchard as the core.

Despite these changes, the Celtics remain above the luxury tax line by approximately $15 million, limiting their ability to sign high-salary players without further roster adjustments. The team regained access to the mid-level exception, a valuable tool for signing free agents, but their payroll still hovers near the second apron, making blockbuster signings challenging. Recent additions like Luka Garza and Josh Minott on minimum contracts reflect a strategy of adding cost-effective depth rather than chasing superstars.

Rumored Superstar Targets: A Closer Look

Damian Lillard

One of the most prominent names linked to the Celtics is Damian Lillard, a nine-time All-Star who became a free agent after the Milwaukee Bucks waived him following a torn Achilles injury in the 2025 playoffs. Reports indicate that Jayson Tatum was actively recruiting Lillard, with the two communicating during the offseason. Lillard, now 35, is expected to miss the entire 2025-26 season to rehabilitate, with a player option for 2027-28. His availability as a free agent was a surprise, given his $112.6 million contract, but the Bucks opted to sign Myles Turner instead, freeing Lillard to explore new opportunities.

While Lillard’s scoring prowess and clutch playmaking make him an attractive target, his age and injury history raise concerns. An Achilles tear is one of the most severe injuries in basketball, and even players like Kevin Durant, who returned to All-Star form after a similar injury, required significant recovery time. Lillard’s inability to play in 2025-26 means he would not address the Celtics’ immediate needs, and his $54 million player option for 2027-28 could strain Boston’s cap further. Even if the Celtics sign him, his diminished athleticism and uncertain recovery timeline make it unlikely he returns to superstar status, rendering him a risky long-term investment.

Ben Simmons

Another name floated in rumors is Ben Simmons, the former No. 1 overall pick and two-time All-Defensive team selection. Simmons, a free agent in 2025, is reportedly considering the Celtics among four potential destinations. The Celtics view Simmons as a defensive replacement for Jrue Holiday, leveraging his elite playmaking and versatility. However, NBA insider Matt Vautour has strongly advised against this move, citing Simmons’ offensive limitations and controversial tenure with the Philadelphia 76ers.

Simmons’ refusal to play during his 2021-22 holdout with the 76ers and his subsequent struggles with the Brooklyn Nets have tarnished his reputation. His former teammate Georges Niang, now with the Celtics, expressed frustration with Simmons’ lack of commitment, highlighting the risk of signing him. At 29, Simmons has not been a consistent offensive contributor since his rookie years, and his inability to shoot from outside limits his fit in Boston’s spacing-heavy system. While his defensive skills and passing are intriguing, Simmons is far from a superstar in his current form, and signing him would likely not elevate the Celtics to contender status.

Russell Westbrook

NBA insider Robbie Stratakos of Fox Sports has named the Celtics as a “best fit” for Russell Westbrook, a nine-time All-Star and former MVP who remains unsigned deep into the 2025 free agency period. Westbrook, now 36, could serve as a bench scorer alongside Simons, Pritchard, and White, providing veteran leadership and energy. However, Westbrook’s inefficiencies as a shooter and his ball-dominant style clash with Boston’s system, which relies on ball movement and three-point shooting.

Westbrook’s recent stints with the Clippers and Nuggets showed flashes of his athleticism but also highlighted his declining impact. His addition would be a “bargain-bin” move, as Stratakos notes, but it would not address the Celtics’ need for a transformative star. Westbrook’s high-energy play could provide a temporary boost, but his age and fit issues make him a suboptimal choice for a team aiming to compete in the Eastern Conference.

Why These Signings Fall Short of Superstar Status

While Lillard, Simmons, and Westbrook are marquee names, none currently qualify as superstars capable of carrying the Celtics in Tatum’s absence. Lillard’s injury and age diminish his immediate impact, Simmons’ offensive limitations make him a role player at best, and Westbrook’s inefficiencies and declining production limit his upside. The Celtics’ championship aspirations require a player who can complement Jaylen Brown’s scoring and Derrick White’s two-way play while filling the void left by Tatum. None of these rumored targets fully meet that criteria.

Moreover, the Celtics’ financial constraints make it difficult to pursue other superstars. The team’s proximity to the second apron limits their ability to offer max contracts, and their trade assets, including the No. 28 and No. 32 picks in the 2025 NBA Draft, are not enough to land a game-changer without including core players like Brown or White. The departure of Porzingis and Holiday has already weakened the roster, and further trades could disrupt chemistry without guaranteeing a significant upgrade.

Alternative Trade Targets

Recognizing the limitations of free agency, the Celtics have been linked to trade targets like Pascal Siakam and Walker Kessler. Siakam, a versatile forward with the Indiana Pacers, could address Boston’s frontcourt depth issues, providing scoring and playmaking. Kessler, a shot-blocking center with the Utah Jazz, offers defensive stability at a low cost. However, acquiring either player would likely require sacrificing valuable assets, such as draft picks or young players like Sam Hauser or Payton Pritchard, which the Celtics are hesitant to do.

These targets, while intriguing, are not superstars either. Siakam is a high-level starter but lacks the game-changing impact of a healthy Tatum, and Kessler is a role player with limited offensive upside. The Celtics’ trade strategy appears focused on maintaining competitiveness while preserving flexibility for Tatum’s return, rather than chasing a blockbuster deal that may not be feasible.

The Impact of Jayson Tatum’s Absence

Tatum’s injury is the single biggest factor shaping the Celtics’ offseason. As the face of the franchise, his absence for the 2025-26 season leaves a massive void in scoring, leadership, and versatility. Jaylen Brown, now the unquestioned alpha, is a dynamic scorer but cannot carry the team alone in a loaded Eastern Conference featuring teams like the New York Knicks, Philadelphia 76ers, and Milwaukee Bucks. The Celtics’ trades of Porzingis and Holiday, while financially prudent, have further depleted their star power, making it harder to compete without a significant addition.

The Celtics’ front office, led by Brad Stevens, is navigating a delicate balance: building a playoff-caliber team around Brown and White while ensuring cap flexibility for Tatum’s return. However, the lack of available superstars on the market and the team’s limited trade assets make it unlikely they can land a player capable of filling Tatum’s shoes, even temporarily.

The Role of Rivalry and Organizational Pride

Similar to the Golden State Warriors’ reluctance to trade Jonathan Kuminga to a rival, the Celtics’ decisions are influenced by their rivalry with teams like the Philadelphia 76ers. Signing Simmons, a former 76er, could be seen as a risky move given his history with the franchise and the potential for locker room tension, especially with Niang on the roster. This dynamic underscores how organizational pride and rivalries can shape roster decisions, sometimes at the expense of pure basketball logic.

The Boston Celtics’ pursuit of a superstar signing in 2025 is fraught with challenges. While rumors of interest in Damian Lillard, Ben Simmons, and Russell Westbrook have generated buzz, none of these players are likely to restore the Celtics to championship contention. Lillard’s injury, Simmons’ offensive limitations, and Westbrook’s declining impact make them suboptimal fits for a team in need of a transformative star. Financial constraints, a thinned roster, and the absence of Jayson Tatum further complicate Boston’s ability to land a game-changer.

As the 2025-26 season approaches, the Celtics must focus on maximizing their current core of Jaylen Brown, Derrick White, and Anfernee Simons while exploring cost-effective additions through the mid-level exception or trades. The team’s long-term goal is to remain competitive until Tatum returns, but the lack of available superstars and the limitations of the rumored targets suggest that Boston may miss out on a blockbuster signing, even if the latest rumors come true. The road back to the NBA Finals will be a challenging one, requiring strategic patience and a bit of luck in a highly competitive league.