Heading into the offseason, it was expected that Jrue Holiday would be traded. The Boston Celtics need to shed salary and get under the second apron. As a result, Holiday was a clear trade candidate, with three years left on his four-year $134 million contract. However, the Portland Trail Blazers were an unexpected landing spot for Holiday. In return for Holiday, the Celtics got Anfernee Simons and two second-round picks. Let’s dive into why this deal is logical for the Celtics.
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
Brad Stevens Strikes Again With an Amazing Jrue Holiday Trade
Why the Celtics Won the Jrue Holiday-Anfernee Simons Trade
Holiday is undoubtedly still a highly impactful player as a defender, spot-up shooter, and connective playmaker. For Portland, he’ll be an incredible veteran presence and make a quality all-around impact. Regardless, at 35 and showing signs of decline as a scorer, it was unclear what Holiday’s value would be on the open market.
With the deal complete, it’s safe to say that Brad Stevens maximized Holiday’s value. Simons is a deadly sniper from beyond the arc, making him an ideal fit in Joe Mazzulla’s system. This past season, Simons averaged 19.3 points, 2.7 rebounds, and 4.8 assists on 42.6/36.3/90.2 shooting splits. As a three-point scorer, shot creator, and playmaker, Simons is a perfect fit for the Celtics. Getting a highly productive player and any form of draft capital is a massive win for the Celtics in a Holiday trade.
Furthermore, Simons is just 26 and is on an expiring $27.6 million contract. This move also saves the Celtics $4.8 million next season. It’s possible that Simons could be a long-term fit with the Celtics on a similar contract. As a result, Boston may look to extend him. Alternatively, if his deal comes off the books next season, the Celtics could save some significant money. Perhaps the Celtics end up re-routing Simons to save more money. Regardless, given his clear fit in the system, the first scenario seems the most likely.
Without Jayson Tatum, Simons will provide some much-needed scoring. However, when Tatum returns, Simons will fit like a glove next to him, and Jaylen Brown with his elite spot-up shooting. Simons gives the Celtics a chance to be competitive in the East next year and could eventually help get the Celtics back to contention when Tatum is fully healthy in the 2026-27 season. From all angles, this deal was a no-brainer for the Celtics.
The Last Word
Brad Stevens has proven to be one of the best general managers in the league and has made some awesome trades over the years. The Holiday/Simons swap is just the latest example of this. With Kristaps Porziņģis likely being the next domino to fall as Boston continues to shed salary, Celtics fans should be grateful that they are in good hands with Stevens. Ultimately, the Celtics are poised to remain fairly competitive next season, and Simons should be a big part of that.
Featured image: © David Butler II-Imagn Images
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