Blazers Send Anfernee Simmons to Celtics for Jrue Holiday in Blockbuster Trade

The NBA offseason is barely a day old, and a massive trade has already been completed. The Portland Trail Blazers have acquired Jrue Holiday from the Boston Celtics.

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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. https://t.co/2TMs5Cd8qn
— Shams Charania (@ShamsCharania) June 24, 2025

NBA insider Shams Charania revealed the news on X.

"BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN," the original post from Charania reads.

"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," Charania added.

The Trail Blazers get a solid veteran in Holiday, who the team had acquired in the trade for Damian Lillard, but he was sent to Boston for two first-round picks.

Holiday averaged 11.1 points, 4.3 rebounds, and 3.9 assists per game. He also shot a 44.3 field goal percentage during the 2024 season. He also had a 35.3 3-point percentage.

Though losing Simons is going to be tough to deal with, the Blazers get a solid contributor and veteran presence in Holiday.

Portland was on the cusp of playing in the play-in tournament, but they just missed the mark by only a few wins. At 36-46, the team was close to sneaking into the tournament, but that was not the case.

After a four-game win streak in the middle of March, the Trail Blazers rifled off four losses at the end of of the month. This was coupled with a 4-3 final stand in the last seven games of the season.

The Trail Blazers could have gotten into the play-in with a handlful of wins, and having a talent like Holiday could help that fact. He was a crucial member of the Celtics' championship run in 2023, and was also very active in the playoffs.

Holiday's experience is definitely needed on a younger team. Again, losing Simons is going to impact the Blazers' overall scoring, but Holiday can balance that out with his experience, imparting those skills onto the younger core players.

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