Celtics
Holiday played a key role in helping the Celtics win a championship in 2024.
The Boston Celtics are reportedly breaking apart some of their championship core in search of some salary relief.
According to ESPN’s Shams Charania, the Celtics are trading guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks.
MassLive’s Brian Robb reported that the two second-round picks are a 2030 Knicks pick and a 2031 Blazers selection.
“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,” Charania added on X. “Simons joins Boston on an expiring contract.
Holiday, 35, played two seasons with the Celtics. His arrival via trade from Portland in October 2023 put an already strong Boston roster over the top.
An elite defender out of the backcourt who added some championship pedigree to Boston, Holiday played a key role in the Celtics’ run to a championship in 2024. During the 2024 playoffs, he averaged 13.2 points, 6.1 rebounds, and 4.4 assists per game while drawing daunting defensive assignments.
He appeared in 62 games with Boston this past season, averaging 11.1 points, 4.3 rebounds, and 3.9 assists per game.
Holiday was initially envisioned as a long-term fixture during Boston’s contention window, especially after signing a four-year, $135 million extension with the Celtics in April 2024.
But with Boston potentially looking at a bridge year in 2025-26 following Jayson Tatum’s Achilles injury and the Celtics needing to get under the restrictive second apron of the NBA’s luxury tax threshold this summer, the writing was on the wall that the team needed to shed salary.
“We still have a really, really great opportunity and a great window to be successful and win a championship again,” Holiday told reporters after Boston’s 2024-25 season ended in the second round. “I think the talent that we have on this team, not only on the court, but the coaching staff all the way up to (Celtics president of basketball operations) Brad [Stevens], has been amazing. So, the opportunity to win is now, and I still want to be a part of that.”
While Boston is only reducing their payroll by $4.1 million by dealing Holiday and taking on Simons’ expiring contract ($27.6 million), the Celtics are also decreasing their looming tax penalties by around $41 million by getting Holiday’s contract off the books, per NBA cap analyst Yossi Gozlan.
It remains to be seen if Simons factors into Boston’s plans moving forward due to that expiring deal. But, the 26-year-old guard was a productive player this past season for Portland, averaging 19.3 points and 4.8 assists per game.
With Tatum sidelined, Simons could be in line to be a featured player for Boston in 2025-26 alongside Jaylen Brown.
“Even after dealing Holiday, Stevens and the Celtics still have plenty of work to do when it comes to retool this roster and clearing up more cap space, Charania added on X. “An extremely active offseason begins for the Celtics with the trade of Jrue Holiday, who played a critical role in Boston’s 2024 NBA championship.
“The Celtics remain engaged in trade talks surrounding multiple key players on the roster, sources said.”
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