The Jrue Holiday-Anfernee Simons trade is another win for the Boston Celtics.

Feb 12, 2025; Denver, Colorado, USA; Portland Trail Blazers guard Anfernee Simons (1) dribbles the ball up court in the first quarter against the Denver Nuggets at Ball Arena. Mandatory Credit: Isaiah J. Downing-Imagn Images | Isaiah J. Downing-Imagn Images

The Boston Celtics were rumored to be making changes to their roster to get under the 2nd apron and this trade signals just that. After acquiring Jrue Holiday in the trade from the Milwaukee Bucks for Damian Lillard in 2023, the Portland Trail Blazers traded Holiday to Boston who was desperate for a defensive guard after they moved Marcus Smart.

Holiday proved to be an intricate part of the Celtics championship run in 2024. Although Boston would have loved to find a way to keep him around, it wasn’t going to work given their situation. Boston is over the 2nd apron which can severely limit team building. For the Celtics, Holiday is an aging guard at 35 years old on a hefty contract. Acquiring Anfernee Simons was about saving money while also getting younger in the process.

As for Portland, it is clear that they want to turn the page to Scott Henderson. After all, the franchise used their 3rd overall pick in 2023 to draft the young guard. After trading Lillard, the Blazers hoped that Henderson could be their future franchise Point Guard. However, in the midst of this, Simons had been breaking out as a scorer. While he was never projected to be a positive defender, Simons broke out during the 2021-2022 season. He upped his scoring average from 7.8 points per game to 17.3 points per game in just one season. Simons would then go on to average 20.7 points per game combined over the next three seasons.

It was clear that Simons was a talent scorer and Portland rewarded him for it. At age 23, the Blazers signed Simons to a 4-year deal worth $100M. While that may seem like a lot of money, Holiday still makes more money on his contract that he signed when he was still in Milwaukee and again when he got to Boston. The key to this trade is that Holiday will be owed over $30M per year for the next three seasons. He also has a $37M player option after his age-37 season.

The Celtics would rather take a chance on Simons for a year than continue to pay Holiday well into his late thirties. If Boston doesn’t see a fit with Simons long-term, they can let him enter free agency after next season. Unlike with Holiday, there is no pressure to commit to Simons long-term. With Tatum out, Simons might be looked at as a bridge player until he gets back healthy again.

The issue for Portland is that they traded a young player for an aging one who makes more money. Although the Blazers felt that Simons doesn’t fit their vision long-term, it’s hard to see why they would be interested in taking on his contract. If a defensive-minded guard is what Portland was looking for, Marcus Smart would have been a better option. Not only is Smart four years younger than Holiday at 31, but he’s on a cheaper and shorter contract. Perhaps money isn’t an issue for Portland, but it’s hard to imagine them committing so much money to an aging guard like Holiday.