Apr 11, 2025; Boston, Massachusetts, USA; Boston Celtics owner Wycliffe K. Grousbeck presents the Red Auerbach award to guard Jrue Holiday (4) before a game against the Charlotte Hornets at TD Garden. Mandatory Credit: Eric Canha-Imagn Images

Just a year ago, it appeared as if the Boston Celtics could be forming a true dynasty in the NBA after winning the NBA championship in the 2023-24 NBA season. But on Monday, the organization made its first move in light of Jayson Tatum’s torn Achilles injury, which appears to suggest a slight rebuild may be coming in Boston.

Tatum’s injury was devastating in multiple ways. For one, it all but ensured that they would ultimately lose to the New York Knicks in the second round of these past playoffs.

Unfortunately, it also means that the organization’s plans for the upcoming 2025-26 season have appeared to change. Tatum is expected to miss a vast majority of the season. And in light of this, the organization decided to trade away an aging cornerstone of the organization who contributed heavily in their recent success.

First reported by ESPN’s Shams Charania, the Celtics agreed to a trade on Monday with the Portland Trail Blazers that will see Jrue Holiday head to Portland. In return, the Celtics will receive Anfernee Simons and two second-round picks.

Simons is certainly no slouch, averaging 19.3 points per game this past season. But still, given Holiday’s excellent ability to impact the game on both sides of the ball, it’s hard not to see this as a bit of a downgrade from a short-term perspective.

But, at 35 years of age, Holilday may start to regress in the near future. And considering Tatum’s injury for much of the 2025-26 NBA season, it seems as if Celtics GM Brad Stevens has made it a point for the team to get younger.

Naturally, many NBA fans had plenty to say about this move. Somewhat surprisingly, Celtics fans were largely in favor of the move given where the team is currently at with Tatum’s injury.

About Reice Shipley

Reice Shipley is a staff writer for Comeback Media that graduated from Ithaca College with a degree in Sports Media. He previously worked at Barrett Sports Media and is a fan of all things Syracuse sports.