In a surprising move shortly after the NBA Finals, the Boston Celtics have traded veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round draft picks. This deal marks a rare instance where a recent championship team parts with an experienced veteran, while a younger, rebuilding side seeks to accelerate its championship window by acquiring a proven, although aging, star.
This unexpected trade immediately raises questions about who benefits more. Evaluating the implications for both the Celtics and Trail Blazers provides insight into the strategic gambles taken by each franchise.
Boston Celtics Capitalize on Flexibility and Younger Talent
Assessing Jrue Holiday’s current level of play is key to understanding Boston’s motivations. Approaching his 35th season, Holiday recently averaged 11.1 points per game, his lowest output since entering the league, despite playing on a team designed to maximize spacing and offensive efficiency. His defensive prowess, once elite, appears to be diminishing, with his best matchups now more commonly wing players rather than the quickest point guards.
Although still useful, Holiday’s contract is hefty and likely out of proportion to his declining production. He is set to earn $32.4 million in the coming season, increasing to $37.2 million by his age-37 campaign through a player option. This steep financial commitment for a player past his prime makes his contract a negative asset in Boston’s roster construction.
By moving Holiday, the Celtics not only shed the burden of these remaining expensive years but also gain valuable assets. The two second-round picks obtained add to Boston’s future flexibility. Anfernee Simons arrives on an expiring deal worth about $27.7 million next season, which Boston can decline to extend, thereby gaining cap space toward their goal of dipping below the second salary cap apron. This immediate financial relief alone justifies the trade from Boston’s standpoint.
Beyond the worst-case scenario, Simons offers significant upside. The 26-year-old guard has proven himself as a potent scorer, averaging 20.7 points per game since becoming a starter and shooting 37.4% from beyond the arc on nearly nine attempts per game. His offensive firepower fits perfectly within Boston’s preference for sharpshooters, and while his defensive weaknesses contributed to Portland’s decision to trade him, Boston’s strong defensive tandem led by Jayson Tatum and Jaylen Brown could mitigate those vulnerabilities.
Simons is also still young, with potential for growth. Boston’s current injury landscape, particularly with Tatum sidelined, makes adding a player of Simons’s offensive caliber especially valuable for maintaining competitiveness. If Simons can thrive as a complementary scorer or high-end sixth man, he could become a long-term asset. Considering this, Boston’s trade gains represent either vital cap flexibility or a promising young contributor—both valuable outcomes for the reigning champions.
Portland’s Risky Bet on Veteran Leadership and Immediate Impact
The Portland Trail Blazers’ acquisition of Jrue Holiday signals an aggressive shift toward a win-now approach, but the costs and strategic reasoning invite scrutiny. Portland’s late-season performance showed some competitiveness, with a 13-14 record after the All-Star break and a top-five league defense. While not a contender, the Blazers are far from a complete rebuild.
Their 2022 and 2023 lottery picks, Shaedon Sharpe and Scoot Henderson, have shown promise but struggled to receive consistent offensive roles due to Anfernee Simons’s heavy usage. By moving Simons, Portland aims to clear space for their young guards to assume leadership roles without sharing possessions. However, Jrue Holiday, while officially a guard, now defends mostly forwards and may not command as significant a role offensively, particularly with other guards emerging. His arrival could thus limit offensive opportunities for Sharpe and Henderson.
However, Holiday’s reputation extends beyond statistics. He is widely admired as a teammate and leader, having won the Twyman-Stokes Teammate of the Year award three times and the NBA Sportsmanship Award twice. He also recently received the Kareem Abdul-Jabbar Social Justice Champion title for the 2024-25 NBA season. Portland likely hopes Holiday’s mentorship mirrors the positive impact Chris Paul had on Shai Gilgeous-Alexander in Oklahoma City, nurturing the team’s young core through his professionalism and leadership.
These reasons paint a plausible, if modest, rationale for Portland’s investment. Yet, acquiring a three-time veteran player aged 35 and older on a $104 million contract over three years is an expensive approach to securing locker room mentorship. Lesser contractual commitments to veteran presence, through minimum deals or coaching leadership—head coach Chauncey Billups is himself a seasoned guard and mentor—might have sufficed.
From a performance standpoint, the trade’s benefits seem limited. Portland’s offense ranked 20th post-All-Star break with Simons, indicating struggles in either creation or shooting. Simons’s departure removes a major offensive weapon, and while Holiday is a solid defender, shooting efficiency from deep has been a concern. Holiday’s below-average three-point shooting last season contrasts with Portland’s already weak perimeter shooting stats, causing questions about offensive improvements.
Defensively, Holiday remains versatile and switchable, likely bolstering Portland’s strong defensive rankings seen post-All-Star. When paired with wings like Deni Avdija and Toumani Camara, the team could apply intense ball pressure through switching. Despite this boost, Portland’s competition in the Western Conference remains fierce, with teams like the Rockets (now with Kevin Durant), Lakers, Warriors, Clippers, Nuggets, and Timberwolves all vying for playoff spots. Emerging threats like Victor Wembanyama further crowd a challenging field, suggesting Portland may struggle to rise beyond a play-in position.
The flaws in Portland’s gamble become clearer off the court. The team once had a potential $50 million-plus cap space opening by 2026, which is now largely consumed by Holiday’s large contract. They also retain Jerami Grant on another substantial deal, resulting in over $73 million in combined salaries for the 2027-28 season for two older veterans on a young team. This financial burden threatens flexibility, especially as young stars Sharpe and Henderson become extension-eligible and Camara faces a new contract soon.
This mirrors a familiar pattern under the team’s current management. The Blazers have tended to hold veteran players too long, often resulting in trades with downgraded returns, as seen with Damian Lillard’s delayed trade and more recently with Jerami Grant’s steep contract and trade demands. If Portland had moved Simons earlier, they might have secured higher-value draft assets, following examples like Orlando’s recent multi-pick trade for Desmond Bane.
Despite these concerns, there is still room for optimism. If Holiday’s veteran presence and on-court contributions help Sharpe and Henderson reach star potential, this risk could be justified. However, the long-term danger of large, expensive contracts on aging players looms over Portland’s efforts, marking the trade as a significant gamble at best.
Implications and Outlook for Both Teams
For the Boston Celtics, the trade offers meaningful salary relief and the potential to add a dynamic, younger offensive piece in Anfernee Simons. This move aligns with their strategy to remain competitive in the near term while managing salary cap constraints and planning for future roster flexibility. If Simons reaches his ceiling, Boston benefits both during Jayson Tatum’s recovery and when he returns to lead the team again.
The Portland Trail Blazers’ decision reflects a sense of urgency and belief in the growth of their young guard duo of Shaedon Sharpe and Scoot Henderson. The hope is that Jrue Holiday’s blend of experience, defense, and leadership will accelerate their development and strengthen the team’s playoff push. However, the heavy financial commitments and limited immediate upside raise questions about the sustainability and prudence of this direction.
Ultimately, this trade encapsulates a broader tension in the NBA between rebuilding with youth and chasing immediate relevance, with the Celtics prioritizing cap space and potential growth, while the Trail Blazers wager on veteran guidance amid a crowded Western Conference. The coming seasons will reveal whether Portland’s high-stakes gamble pays off or compounds their challenges.