Jrue Holiday to Portland: What the Celtics-Blazers Trade Means for Both Teams

By Edcel Panganiban June 27, 2025 07:15

In a significant NBA offseason move, the Boston Celtics have traded veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for young guard Anfernee Simons and two future second-round draft picks. This deal, announced on June 23, 2025, carries substantial implications for both franchises as they navigate their respective futures.

Celtics’ Perspective: Financial Relief and Roster Flexibility

For Boston, the trade is primarily a financial and strategic decision. Holiday, 35, is under a hefty four-year, $135 million contract extension signed in 2024, with $104.4 million remaining over the next three seasons. The Celtics faced nearly $500 million in total payroll and luxury tax penalties if they retained their full roster, a burden made more acute after star forward Jayson Tatum suffered a season-ending Achilles injury in the Eastern Conference semifinals. As a source close to the team explained, "There was no universe in which the franchise kept [Holiday]. It would just be too expensive for a team that quite possibly wouldn't have its best player on the court for the postseason next year".

Trading Holiday alleviates Boston’s luxury tax strain and opens up valuable cap space, enabling the Celtics to pursue roster upgrades through the draft and free agency. While Holiday was a crucial part of Boston’s 2024 NBA championship run averaging 11.8 points per game and earning his sixth All-Defensive Team selection his departure signals a transition phase for the Celtics. Anfernee Simons, the 26-year-old guard coming from Portland, offers scoring upside with a career-high 22.6 points per game last season and is entering the final year of his $100 million contract, making him a younger, more flexible asset for Boston’s backcourt.

Trail Blazers’ Perspective: Veteran Leadership and Defensive Prowess

Portland, meanwhile, reacquires a familiar face in Holiday, who was briefly with the Trail Blazers following the Damian Lillard trade in 2023 before being sent to Boston. At 35, Holiday brings elite defensive skills, veteran leadership, and championship experience to a Blazers team in the midst of rebuilding. Despite averaging career lows in points (11.1), rebounds (4.3), and assists (3.9) last season, Holiday’s impact extends beyond statistics. He is a two-time NBA champion, two-time All-Star, and six-time All-Defensive Team member, known for his professionalism and locker room presence.

However, Holiday reportedly expressed dissatisfaction with the trade, reportedly being "pissed" about moving to Portland, a team with less immediate championship contention prospects than Boston. A source noted, "He’s not happy with this deal... I’ll be surprised if Portland doesn’t move him on if they can, because right now he does not want to go there". Nonetheless, Portland’s front office likely values Holiday’s ability to mentor younger players and stabilize the roster during their rebuild.

Trade Grades and Outlook

Analysts grade the trade as favorable for both sides given their circumstances. Boston gains financial flexibility and a promising young scorer in Simons, while Portland adds a seasoned defender and playmaker in Holiday who can contribute immediately and help develop their young core.

In summary, the Jrue Holiday trade marks a pivotal moment for two franchises with contrasting trajectories. The Celtics, constrained by salary cap realities and injury setbacks, opt for a youth-infused, cost-controlled approach. The Trail Blazers, embracing a rebuild, acquire a veteran presence who embodies defensive excellence and playoff experience. As the 2025-26 NBA season approaches, both teams will look to leverage this trade toward their long-term goals.

This trade underscores the evolving nature of team-building in the NBA, balancing financial prudence, player development, and championship aspirations. As Celtics President Brad Stevens noted in a recent press conference, "Sometimes tough decisions have to be made for the greater good of the franchise’s future". Meanwhile, Portland’s management remains optimistic about Holiday’s role, viewing him as a cornerstone in their next chapter.