Jrue Holiday Reportedly Traded to Blazers, Celtics Get Anfernee Simons, Draft Picks

Jrue Holiday's time with the Boston Celtics is over.

Boston traded the veteran guard to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round NBA draft picks, per Shams Charania of ESPN:

Charania also noted the Celtics "remain engaged in trade talks surrounding multiple key players on the roster."

The Sacramento Kings and Dallas Mavericks were among teams also reportedly interested in Holiday before the deal, per NBA Insider Jake Fischer. The Blazers still don't plan to flip the veteran point guard and will "definitely" keep him to try to improve in the Western Conference, per Fischer.

The idea of the Celtics trading Holiday picked up steam after they were eliminated by the New York Knicks in the second round. Jay King of The Athletic reported after that series that "several contending teams" were interested in the UCLA product should Boston decide to shop him.

This offseason was also one of uncertainty for the storied franchise, as Jayson Tatum suffered a ruptured Achilles in that loss to the Knicks. It could leave him sidelined for most, if not all, of the 2025-26 campaign, bringing into question how much of a title contender the team could be as currently constructed.

What's more, a group led by Bill Chisholm agreed to purchase the Celtics at a valuation of $6.1 billion in March. That introduced another variable when it came to managing the roster and overall finances, especially since the Celtics were previously projected to have the highest payroll in NBA history:

With Holiday signed through the 2026-27 season with a $37.2 million player option for 2027-28 to go along with the $32.4 million in base salary in 2025-26 and $34.8 million in base salary in 2026-27 he was set to make, he was a candidate to be moved and was ultimately traded.

Still, he told reporters after the playoff loss he wanted to stay with the Celtics and added, "I think that we had the best team in the league."

While he didn't get his wish with this trade, he now has the opportunity to bolster an already impressive resume on a new team.

That resume includes two championships, six All-Defensive selections, two All-Star Game nods and two Olympic gold medals (2020 Tokyo Games and 2024 Paris Games). He is one of the best defensive players of his generation and won two of the last five titles, helping propel the Milwaukee Bucks to the championship in 2021 and the Celtics to one in 2024.

Holiday is known for his hounding perimeter defense, but he has also averaged 15.8 points and 6.2 assists per game in his career while shooting 37 percent from deep.

His ability to extend his offensive arsenal beyond the arc helped him take advantage of spacing created by playing alongside stars such as Giannis Antetokounmpo and Tatum in recent years, and he will look to do the same at his newest destination.

Even though he will be 35 years old during the upcoming campaign, he was still effective in 2024-25 while posting 11.1 points, 4.3 rebounds, 3.9 assists and 1.1 steals per game as he shot 44.3 percent from the field and 35.3 percent from deep.

Given the veteran leadership he provides, his ability to anchor the perimeter defense and his overall skill set, Holiday figures to be a valuable addition for the Blazers as they try to turn things around after a 36-46 season.

Boston, meanwhile, adds a high-upside guard in Simons who averaged 19.3 points and 4.8 assists per game. The 26-year-old could immediately become a top perimeter threat alongside Jaylen Brown with Tatum injured.