Image Credit: Bob DeChiara-Imagn Images

Boston Celtics Trade Jrue Holiday To Portland Trail Blazers for Anfernee Simons and Two Draft Picks

Jrue Holiday is on the move again.

Image Credit: Bob DeChiara-Imagn Images

The Boston Celtics traded Jrue Holiday to the Portland Trail Blazers in order to acquire Anfernee Simons and two second-round picks. This is the second time Holiday found himself on the move to Portland, following his trade from the Milwaukee Bucks in 2023 for Damian Lillard. He was then transferred to the Boston Celtics soon, but now they get him back in a blockbuster trade deal.

ESPN Insider Shams Charania reported, “Portland makes an aggressive move to re-acquire Holiday, who the franchise originally received from Milwaukee in the Damian Lillard trade in 2023 and later moved to Boston for a deal that included two first-round picks to Blazers. Simons joins Boston on an expiring contract.”

Shams also reported that this is only the beginning for the Celtics, who are engaged in trade talks “surrounding multiple players on the roster.” Holiday spent two seasons with the 18-time champions and played a key role in helping them win the 2024 title. He averaged 11.1 points and 4.3 rebounds per game in the 16th season of the league last season.

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

Inside the Jrue Holiday-Anfernee Simons Trade

It is to be noted that Holiday had two years left on his current deal with the Boston Celtics. He is owed $72 million and has a $37.2 million player option for the third year. With trading him to the Trail Blazers, the Celtics would be able to save around $40 million in tax savings in 2025-26. It would also help them move over the $18 million over the second apron.

Here are the salaries going out

To Boston

Anfernee Simons: $25.9M, $27.7M (UFA, 2026)

* The Celtics get off the combined $72M owed to Holiday in 2026-27 and 2027-28

* Projected $40M in tax savings in 2025-26

* $18M over the 2nd apron

* Simons is extension eligible

To…
— Bobby Marks (@BobbyMarks42) June 24, 2025

As for Simons, the 2018 No. 24 overall pick averaged 19.3 points, 2.7 rebounds and 4.8 assists for the Trailblazers with a 43/36/90 shooting split. He signed a four-year deal with the Trail Blazers, which was worth $100 million. However, he is set to enter the final year of the contract this fall.

Anfernee Simons

Boston Celtics

Jrue Holiday

Garima Ranawat

Garima is a sports writer with around two years of experience in Indian sports and a newfound interest in the NBA. Inspired by the leadership of cricketing legend MS Dhoni, she wishes to bring in newer perspectives to the NBA fanatics with her writing.