Skip to main content

CELTICS-BULLS TRADE FRENZY: Proposed Swap Sends Simons to Chicago for Chicago’s DUO of Future Stars!

The Boston Celtics, fresh off their 2024 NBA Championship, are navigating uncharted waters in the 2025-26 season. With superstar Jayson Tatum sidelined for the entire year due to a devastating Achilles tear, President of Basketball Operations Brad Stevens faces a daunting challenge: retooling a championship roster while slashing payroll to escape the NBA’s punitive luxury tax first apron. A proposed trade by Hardwood Houdini’s Jack Simone, involving Kevin Huerter and Jalen Smith from the Chicago Bulls, offers a glimpse into Stevens’ strategy to balance youth, depth, and financial flexibility. As the Eastern Conference weakens and trade rumors swirl, can Stevens keep the Celtics competitive without Tatum, or is a full rebuild on the horizon? 

The 2025-26 season marks a pivotal moment for the Boston Celtics, as Jayson Tatum’s injury and the NBA’s stringent luxury tax rules force Brad Stevens to make tough decisions. Trading away championship cornerstones like Jrue Holiday and Al Horford signals a shift toward a younger, cheaper roster. The proposed trade for Kevin Huerter and Jalen Smith, alongside moves like acquiring St. John’s prospect RJ Luis Jr., highlights Stevens’ dual focus: shedding salary while maintaining playoff potential. Let’s break down the trade, its implications, and what it reveals about Boston’s direction.

The Financial Crunch: Navigating the Luxury Tax

The Celtics’ projected payroll for 2025-26, including luxury tax penalties, was a staggering $493 million before Stevens began his cost-cutting mission. The NBA’s second apron, set at approximately $207.8 million, imposes severe restrictions, including frozen draft picks and limited trade flexibility. With Tatum’s $54.1 million supermax contract counting against the cap despite his absence, Stevens must shed at least $20 million to dip below the second apron and an additional $12 million to avoid the first apron. These financial pressures, combined with Tatum’s injury, have paused Boston’s pursuit of Banner 19, prompting a strategic pivot. As ESPN reports, Stevens’ trades of Holiday and Kristaps Porzingis saved over $300 million, bringing the Celtics closer to financial relief while reshaping the roster.

The Proposed Trade: Huerter and Smith for Depth and Youth

Hardwood Houdini’s Jack Simone proposes a trade that would send Anfernee Simons, acquired in the Holiday deal, to the Chicago Bulls for Kevin Huerter and Jalen Smith. This move aligns with Stevens’ goal of acquiring young, cost-effective players who fit the timeline of Tatum (27), Jaylen Brown (29), and Derrick White (31). Huerter, a 27-year-old sharpshooting wing, averaged 10.2 points and shot 36.1% from three last season, offering spacing and versatility. Smith, a 25-year-old big man, brings rim protection and rebounding, averaging 9.9 points and 5.5 rebounds. Both players are in their 20s, with Huerter on a $16.2 million contract through 2025-26 and Smith on a $5.4 million deal with a player option. This trade would save Boston approximately $6 million, edging them closer to the first apron while adding depth. Simone notes that Chicago benefits by shedding Smith’s second-year salary and gaining Simons, a 26-year-old scoring guard who could be flipped for assets like Coby White or Ayo Dosunmu.

The trade fits Stevens’ pattern of targeting undervalued talent. Huerter’s shooting complements Boston’s three-point-heavy system under coach Joe Mazzulla, while Smith provides frontcourt insurance, especially with Al Horford and Luke Kornet likely departing in free agency. However, as Simone warns, these additions could “accidentally” keep Boston competitive in a weakened Eastern Conference, potentially undermining a full rebuild. An X user commented, “Huerter and Smith could keep the Cs in the playoffs, but is that what Stevens wants without Tatum?” This tension—competing versus rebuilding—defines Boston’s offseason.

Stevens’ Strategy: Youth Over Veterans

Stevens’ recent moves, like trading Georges Niang for St. John’s prospect RJ Luis Jr., signal a preference for youth over veteran experience. Luis, a 22-year-old wing with raw athleticism, represents the “diamonds in the rough” Stevens has a knack for finding, similar to past successes like Sam Hauser and Luke Kornet. Trading Holiday ($32.4 million) and Porzingis ($30.7 million) for younger, cheaper players like Simons ($27.7 million) and Niang (later flipped) slashed roughly $135 million in salary while netting draft picks. This approach mirrors Stevens’ philosophy of building around Tatum’s eventual return, projected for 2026-27, when he’ll be 29 and in his prime.

However, Stevens’ reluctance to tank, as noted by NBC Sports Boston’s Chris Forsberg, suggests he’s not fully embracing a rebuild. With Jaylen Brown, the reigning Finals MVP, and Derrick White leading the core, alongside rising star Payton Pritchard, the Celtics could still vie for a playoff spot. An X post captured the sentiment: “Stevens is playing 4D chess—cutting costs but keeping enough talent to avoid a lottery season.” Yet, Simone argues that adding a scoring guard like Simons risks winning “too many games,” complicating a potential top-10 pick in the 2026 draft, which could be a valuable asset when Tatum returns.

The Eastern Conference Landscape: Opportunity or Trap?

The Eastern Conference’s relative weakness in 2025-26, with teams like Milwaukee potentially losing Giannis Antetokounmpo, creates an opening for a Tatum-less Celtics squad to compete. Mazzulla’s competitive ethos and Boston’s depth—bolstered by players like Huerter, Smith, and Pritchard—could secure a play-in spot or better. However, this competitiveness could conflict with Stevens’ long-term vision of acquiring draft capital for a reloaded roster in 2026-27. An X user noted, “The East is wide open, but without Tatum, do we want to scrape into the playoffs or aim for a high draft pick?” The Huerter-Smith trade, while cost-effective, risks pushing Boston toward short-term success at the expense of long-term gains.

Lessons from Stevens’ Past: Finding Gems

Stevens’ track record of unearthing talent—Hauser, Kornet, and even Derrick White in his Indiana days—suggests he can maximize Huerter and Smith’s potential. Huerter’s shooting and Smith’s defensive upside could thrive in Mazzulla’s system, which emphasizes spacing and versatility. Yet, the departure of veterans like Holiday and Horford, praised as “masterful” by The Ringer for saving $300 million, underscores the financial necessity driving these moves. An X user remarked, “Stevens is a wizard, but losing Holiday and Horford hurts. Huerter and Smith better step up.” The challenge is clear: can Stevens replicate his past success with younger, unproven players while managing expectations in a transitional year?

Brad Stevens’ offseason maneuvering for the 2025-26 Boston Celtics reflects a delicate balancing act: slashing payroll to escape the luxury tax while preserving enough talent to stay relevant in a weakened Eastern Conference. The proposed trade for Kevin Huerter and Jalen Smith, alongside moves like acquiring RJ Luis Jr., showcases Stevens’ strategy of prioritizing youth and financial flexibility as Jayson Tatum recovers. While these moves could keep Boston competitive, they also risk derailing a full rebuild that could secure valuable draft assets for 2026-27. As fans, we’re left wondering: is Stevens building a playoff contender or laying the groundwork for Tatum’s triumphant return? Share your take in the comments—let’s debate the Celtics’ future and whether Huerter and Smith are the right pieces for this new chapter.