April 15, 2013; Auburn Hills, MI, USA; Philadelphia 76ers point guard Jrue Holiday (11) drives past Detroit Pistons point guard Will Bynum (12) during the first quarter at The Palace. Mandatory Credit: Tim Fuller-Imagn Images Tim Fuller-Imagn Images

Ex-Sixers Star Moved in Blockbuster Trade Between Celtics-Blazers

Originally posted on Philadelphia 76ers on SI
By Justin Grasso | Last updated Jun 23, 2025 11:56 PM ET

Jrue Holiday is on the move again. After spending the last two seasons with the Boston Celtics, the former Philadelphia 76ers star was included in a trade to the Portland Trail Blazers.

On Monday night, ESPN’s Shams Charania reported that Holiday was dealt to the Blazers in exchange for Anfernee Simons and multiple second-round picks.

Holiday’s chances of getting traded were high once the Celtics’ season ended in the second round of the 2025 NBA Playoffs. With the payroll starting to rise to uncomfortable levels, the 35-year-old Holiday was viewed as a trade block candidate, along with Boston’s hybrid center, Kristaps Porzingis.

BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN. pic.twitter.com/2ycXQicGkT
— Shams Charania (@ShamsCharania) June 24, 2025

Holiday becomes the first domino to fall, allowing the Celtics to replace his spot on the roster with a 26-year-old guard, who averaged 19 points on 36 percent shooting from deep one season ago.

Meanwhile, Holiday followed up his All-Star season in 2023-2024 with a 62-game showing in Boston for his second season with the team. The veteran guard produced 11 points per game on 44 percent shooting from the field and 35 percent from three. Holiday also averaged four rebounds and six assists per game.

Throughout his career, Holiday has been recognized as one of the best two-way guards in the game. He was a critical addition to the Milwaukee Bucks’ 2021 championship team, and the same can be said about the 2024 NBA Champions, the Celtics.

Before the Celtics landed Holiday two offseasons ago, he was initially traded from the Bucks to the Blazers. Holiday was a key piece in the trade that landed Milwaukee Damian Lillard. Less than five days later, Holiday was sent to Boston. Last year, he inked a four-year extension with the Celtics.

Before the Celtics landed Holiday, the Sixers were rumored to be interested in a reunion with their former guard. The Blazers were more intrigued with what the Celtics had to offer at the time. Two years later, Portland gets him back with three seasons left on his deal.