Boston Celtics' Jrue Holiday dribbles the ball during the second half of Game 3 of an NBA basketball second-round playoff series against the New York Knicks, Saturday, May 10, 2025, in New York.
The Boston Celtics, fresh off their 18th NBA championship win, are shaking up their roster again. Jrue Holiday, whose acquisition last season helped Boston clinch the title, is now being traded back to the Portland Trail Blazers. In return, the Celtics will receive Anfernee Simons and two second-round draft picks, according to ESPN.
Holiday’s Journey Comes Full Circle
Jrue Holiday’s NBA journey has come full circle. Just a season ago, he was sent to Portland from Milwaukee in the Damian Lillard trade. But his time with the Trail Blazers was brief. He was quickly shipped to Boston, where he stepped into the starting line up and played a crucial role in their championship run.
Now, after helping Boston make NBA history, he’s heading back to Portland, a team in rebuild mode.
Boston’s Big Move Signals Change
The decision to trade Jrue Holiday suggests that the Celtics are entering a transition phase. The move follows another recent setback: All-NBA forward Jayson Tatum is set to miss time due to Achilles tendon surgery. With two key starters out, the Celtics are clearly reshuffling their deck.
Holiday was more than just a defender. He brought experience, leadership, and elite defensive skills. In his first season with Boston, he earned his sixth All-Defensive Team selection. However, his scoring dipped to 11.1 points per game — his lowest since his rookie season in 2009–10.
Salary Cap Pressures Behind the Trade
Money played a big role in the decision to part ways with Holiday. The veteran guard is owed $104.4 million over the next three seasons. Given the massive contracts already handed to Jayson Tatum and Jaylen Brown, the Celtics needed some financial breathing room.
Though his scoring declined, Holiday’s value remained high across the league. Several teams — including the Sacramento Kings, Dallas Mavericks, and Toronto Raptors — reportedly showed interest. Ultimately, it was Portland that struck a deal.
Simons Brings Youth and Scoring to Celtics
In Anfernee Simons, the Celtics get a younger, more offensively inclined guard. Simons averaged 19.3 points last season and posted a career-high 22.6 points per game in 2023–24. His scoring ability could help fill the gap left by Holiday’s departure and Tatum’s injury.
Simons is known for his shooting touch and speed, making him a dynamic fit for Boston’s fast-paced offence. At just 25, he also brings long-term upside, something the Celtics might prioritize as they prepare for future seasons.
Holiday Joins Fifth NBA Franchise
For the Holiday, this trade marks the fifth NBA team of his career. Starting with the Philadelphia 76ers, he went on to play for the New Orleans Pelicans, Milwaukee Bucks, and Celtics. He won a title with Milwaukee in 2021 and is a two-time Olympic gold medallist.
Despite a dip in scoring, Holiday remains one of the most respected guards in the league. His career average of 15.8 points over 16 seasons speaks to his consistency and versatility.
What’s Next for Boston and Portland?
The Celtics may have just won a title, but the road ahead looks uncertain. With Tatum sidelined and Holiday gone, Boston will rely heavily on Brown, Simons, and their supporting cast to keep the team competitive.
For the Trail Blazers, bringing Holiday back could be a short-term play, or part of a larger trade strategy. Either way, the deal signals Portland’s interest in bringing veteran leadership to a young squad.
