Celtics Trade Champion Jrue Holiday to Trail Blazers for Anfernee Simons, Draft Assets in Major Roster Shake-Up
In a significant move signaling the start of what’s expected to be a busy offseason, the Boston Celtics have reportedly agreed to trade veteran point guard Jrue Holiday to the Portland Trail Blazers. In return, the Celtics will receive young scoring guard Anfernee Simons and two future second-round draft picks. The reported deal, first broken by ESPN’s Shams Charania and widely confirmed, marks a pivotal shift for both franchises as they prepare for the 2025-26 NBA season.
The trade comes after a 2024-25 season where the Celtics, fresh off winning their 18th NBA championship in 2023-24, saw their title defense derailed by a second-round playoff exit following a serious injury to star forward Jayson Tatum. This setback, coupled with the team’s rapidly escalating salary commitments, fueled speculation that major roster changes were on the horizon.
Why Boston Made the Move: Financial Flexibility and Future Focus
For Boston, the primary motivation behind trading Holiday appears to be financial flexibility and long-term salary relief. Holiday, 35, had two guaranteed seasons remaining on his contract plus a player option for a third, totaling a potential $104.4 million owed. Shedding this commitment, particularly the $72 million due in the 2026-27 and 2027-28 seasons, provides crucial breathing room for a team already deep into the luxury tax.
According to reports citing salary cap expert Bobby Marks, the trade is projected to save the Celtics an estimated $40 million in luxury tax payments for the 2025-26 season alone. Even with this saving, the team was reportedly still $18 million over the dreaded second apron, highlighting the extreme financial pressures they faced. Acquiring Simons, who is on an expiring contract entering its final year ($27.7 million owed in 2025-26) and is extension eligible, offers both potential on-court value and future contractual flexibility.
Beyond the financial aspect, the Celtics acquire a younger player in Simons. While they will undoubtedly miss Holiday’s elite defense, leadership, and unselfish play that were vital to their 2024 championship run, his scoring production saw a dip last season (11.1 PPG, his lowest since his rookie year). Simons, 26, offers a different offensive profile – a high-volume scorer who has averaged over 17 points per game for the past four seasons, including 19.3 last season and a career-high 22.6 the year prior.
Simons’ career 38.1% shooting percentage on 6.5 three-point attempts per game is a key asset that aligns perfectly with Boston’s aggressive offensive scheme, which led the league in both three-point makes and attempts last season. He could seamlessly fit into their guard rotation alongside Derrick White and Payton Pritchard, providing scoring punch and floor spacing.
What it Means for Portland: Veteran Presence or Trade Asset?
For the Portland Trail Blazers, acquiring Jrue Holiday brings a decorated veteran and champion to a young, rebuilding roster. Holiday’s experience, defensive prowess (a six-time All-Defensive player), and stabilizing presence could provide valuable leadership for players like Scoot Henderson. Portland coach Chauncey Billups has emphasized improving the team’s defense, a goal Holiday is uniquely qualified to help achieve.
Interestingly, this marks Holiday’s second brief acquisition by the Blazers. He was initially part of the package Portland received for trading Damian Lillard to Milwaukee in 2023 but was quickly rerouted to Boston without ever playing a game for Portland. This history raises the possibility that the Blazers might choose not to keep the 35-year-old veteran long-term and could explore trading him to a contending team again for further assets, accelerating their rebuild.
Trading Anfernee Simons ends his seven-year tenure with the team that drafted him 24th overall in 2018. Simons had developed into a productive scorer but reportedly struggled at times last season adapting to the full-time point guard role and the team’s faster pace after being accustomed to more half-court sets. Moving to a winning culture in Boston could potentially benefit Simons, allowing him to focus on his scoring strengths within a different system.
The official completion of the trade is expected in July, following the NBA draft and the start of free agency. With multiple reports suggesting the Celtics are engaged in further trade discussions involving other players, this significant transaction appears to be just the initial move in reshaping Boston’s roster for the future.
