Blazers vindicated for Jrue Holiday trade as Celtics sell low on Anfernee Simons

Oct 22, 2025; Boston, Massachusetts, USA; Boston Celtics guard Anfernee Simons (4) during the second quarter against the Philadelphia 76ers at TD Garden. Mandatory Credit: Winslow Townson-Imagn Images
Oct 22, 2025; Boston, Massachusetts, USA; Boston Celtics guard Anfernee Simons (4) during the second quarter against the Philadelphia 76ers at TD Garden. Mandatory Credit: Winslow Townson-Imagn Images | Winslow Townson-Imagn Images

The Boston Celtics have traded Anfernee Simons and a second-round pick to the Chicago Bulls in exchange for Nikola Vucevic and a second-round pick, ESPN's Shams Charania reports. This past summer, the Portland Trail Blazers flipped Simons for Jrue Holiday in a one-for-one swap with the Celtics.

Between Simons, Vucevic, and Holiday, it's clear who is the best player.

Blazers traded Anfernee Simons at the right time

Even at 35 years old with declining athleticism, Holiday has been incredibly impactful for Portland. He's found new life with the Blazers, stepping up in an increased playmaking role to average 14.3 points, 6.7 assists, and 4.5 rebounds on 43/35/76 shooting splits. That bounce-back season has proven Holiday still has plenty of gas left in the tank, boosting his trade value as a result.

Teams like the New York Knicks have inquired about Holiday, and the Blazers would likely be able to receive a package more significant than Vucevic if they were to move on from their veteran guard in the next two days. Having Holiday at least gives them a pathway to acquiring Mikal Bridges, for instance. That never would've been a realistic option if Simons were still in the picture.

Vucevic remains a quality starting center and will provide an immediate upgrade for Boston's frontcourt, but he's also owed $21.5 million and on an expiring contract. It makes sense from the Celtics perspective as it likely signals they expect Jayson Tatum to return in time for a deep postseason run. But in terms of maximizing value, it's clear the Celtics sold low on Simons.

They know Holiday is the better player, but they essentially had to move him in order to duck the second apron. Vucevic is owed roughly $6 million less than Simons, which will further help the Celtics tax situation. But fortunately, the Blazers don't have to deal with that problem. The fact that they had these players on rookie deals and team-friendly contracts means they were able to steal Holiday for limited assets.

His contract could be problematic down the road as the Blazers owe him $37 million when he'll be 37 years old. But they could also proactively get ahead of that situation with a market already emerging for Holiday -- especially given his connections to former Bucks teammate Giannis Antetokounmpo.

In other words, if Portland decides to trade Holiday in the coming days, expect a better return than Vucevic.

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