The Boston Celtics have been a powerhouse in recent years, hoisting the 2024 NBA championship banner and dominating the Eastern Conference. But even the best teams make mistakes, and with Jayson Tatum sidelined by a torn Achilles and the team facing salary cap challenges, the Celtics are poised for a pivotal offseason. A shocking proposal from Bleacher Report’s Matt Velazquez suggests trading Jrue Holiday to the Portland Trail Blazers for Matisse Thybulle, Robert Williams III, and Duop Reath, addressing a 2019 draft blunder and reshaping Boston’s roster. Could this risky move propel the Celtics toward another title run, or is it a gamble too far? Let’s dive into the trade buzz and see what it means for Boston’s future!
The Celtics’ Championship Pedigree and Current Challenges
The Boston Celtics have been a model of consistency, reaching the Eastern Conference Finals multiple times and securing the 2024 NBA title with a dominant roster led by Jayson Tatum, Jaylen Brown, and Jrue Holiday. However, the 2025-26 season brings new hurdles. Tatum’s torn Achilles, suffered late last season, will delay his return, putting pressure on Brown and others to carry the load. Meanwhile, the team’s payroll—pushing against the NBA’s second apron ($207.8 million)—limits flexibility under the league’s strict financial rules.
With Jaylen Brown off the trade table after his 2024 Finals MVP performance, the Celtics are exploring bold moves to maintain their contender status. Trading Jrue Holiday, a championship-caliber point guard with a $30 million salary for 2025-26, could alleviate cap pressure while addressing roster depth. Bleacher Report’s Matt Velazquez ties this potential move to a past mistake: selecting Romeo Langford over Matisse Thybulle at No. 14 in the 2019 NBA Draft. While Langford flamed out, Thybulle became a defensive standout, and acquiring him now could rectify that error.
The Proposed Trade: Holiday to Portland
The proposed deal would see Boston send Jrue Holiday to the Portland Trail Blazers for Matisse Thybulle, Robert Williams III, and Duop Reath. For Portland, Holiday’s veteran leadership and playoff experience would be a boon, especially if they trade Anfernee Simons this offseason. Holiday, a two-time All-Star averaging 19.3 points and 7.9 assists last season, could mentor young stars like Scoot Henderson and elevate the Blazers’ competitiveness in the Western Conference.
For Boston, the trade brings a mix of high-risk, high-reward players:
Matisse Thybulle: A defensive specialist, Thybulle’s All-Defensive Second Team honors in 2021 and 2022 highlight his elite perimeter defense. Limited to 15 games last season due to injuries, he’s a buy-low candidate at $11 million on an expiring contract. His 36.3% three-point shooting last season adds offensive upside, making him a potential 3-and-D fit alongside Brown.
Robert Williams III: A former Celtic, Williams is a dynamic rim protector and lob threat but has been plagued by injuries, playing only 6 games last season. At $12.4 million on an expiring deal, he’s another low-risk gamble. A healthy Williams could reclaim his role as a top-tier defensive big, bolstering Boston’s frontcourt.
Duop Reath: A depth piece at $2 million, Reath averaged 9.1 points and 3.7 rebounds last season, offering size and versatility off the bench.
The trade sheds Holiday’s hefty salary, giving Boston flexibility to navigate the second apron while adding depth to a roster thinned by Tatum’s absence.
Rectifying the 2019 Draft Mistake
Velazquez’s Bleacher Report article frames this trade as a chance to correct Boston’s 2019 draft error. Selecting Romeo Langford over Matisse Thybulle at No. 14 was a misstep—Langford played just 141 NBA games before exiting the league, while Thybulle became a defensive stalwart with the Philadelphia 76ers and Portland. Thybulle’s ability to guard multiple positions would have complemented Tatum and Brown, and acquiring him now could redeem that missed opportunity.
The trade also brings back Robert Williams III, a fan favorite in Boston from 2018-23. Known as “Time Lord” for his game-changing blocks and dunks, Williams was traded to Portland in 2023 for Holiday. His return, albeit risky due to injury concerns, adds emotional resonance and defensive upside. The Celtics are betting on Thybulle and Williams’ expiring contracts to provide short-term impact without long-term financial commitment.
Risks and Rewards
The trade is a gamble with significant risks. Trading Holiday, a proven playoff performer and locker-room leader, could disrupt team chemistry and weaken Boston’s backcourt. Thybulle and Williams’ injury histories—21 combined games played last season—raise concerns about their reliability. If both fail to stay healthy, the Celtics could struggle to replace Holiday’s production, especially with Tatum sidelined.
However, the rewards are enticing. Thybulle’s defense could neutralize opposing wings like Jalen Williams or Luka Dončić, while Williams’ rim protection would anchor the paint alongside Al Horford. Reath adds depth, and the cap relief—shedding $30 million for $25.4 million in expiring deals—gives Boston room to pursue free agents or midseason trades. If the move flops, the expiring contracts limit long-term damage, allowing the Celtics to reset in 2026 when Tatum returns.
Boston’s Broader Offseason Strategy
This trade aligns with Boston’s need to balance immediate contention with financial prudence. With Brown, Derrick White, and Kristaps Porziņģis forming a strong core, adding defensive specialists like Thybulle and Williams could maintain Boston’s elite defense, ranked No. 2 in 2024-25. The Celtics could also explore smaller moves, such as re-signing depth players or targeting buyout candidates, to round out the roster.
Portland’s perspective is equally compelling. Holiday’s arrival could accelerate their rebuild, providing stability and mentorship. If Simons is traded, Holiday could slide into the starting point guard role, forming a dynamic backcourt with Henderson. The Blazers’ willingness to take on Holiday’s contract suggests confidence in their young core, including Shaedon Sharpe and Donovan Clingan.
The Bigger Picture
This trade reflects the Celtics’ delicate balancing act: staying competitive without Tatum while preparing for his return. It also underscores the NBA’s financial landscape, where cap management is as critical as on-court performance. Boston’s front office, led by Brad Stevens, has a history of bold moves, from acquiring Holiday to drafting Brown and Tatum. Trading Holiday would be another high-stakes decision, testing their ability to maximize a championship window.
For Portland, the trade signals ambition to climb the Western Conference standings. Holiday’s veteran presence could mirror Damian Lillard’s impact during his Blazers tenure, guiding a young roster toward playoff contention.
The Boston Celtics are at a crossroads, and trading Jrue Holiday for Matisse Thybulle, Robert Williams III, and Duop Reath could be a game-changer—or a costly misstep. This bold proposal corrects a 2019 draft mistake, adds defensive depth, and eases cap pressure, but risks losing a championship cornerstone. As the offseason heats up, all eyes are on Boston to see if they pull the trigger. Celtics fans, what’s your take? Is trading Holiday a genius move to keep the title dream alive, or too big a gamble?