The Boston Celtics were previously rumored in May they would enter a roster shuffle, and it happened just this week. The management knew that it needed to free up cap space so it could avoid penalties associated with the league's new collective bargaining agreement regulations.

Within 24 hours, Brad Stevens and the Celtics' front office completed two significant trades involving Jrue Holiday and Kristaps Porzingis two days before the 205 NBA Draft.

Holiday to Portland, Porziņģis to Atlanta in Cap-Saving Deals

NBA Trade Rumors: Did Boston Celtics Win Financially After Trading NBA Trade Rumors: Did Boston Celtics Win Financially After Trading
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The first domino toppled late Monday evening when the Celtics swapped Jrue Holiday to the Portland Trail Blazers. Holiday, who just signed a four-year, $134 million extension with Boston, had $104.4 million left on that contract.

Only one day later, the Celtics traded Kristaps Porziņģis to the Atlanta Hawks in a three-team trade. Porziņģis, whose final year of contract was approaching, was to make $30.7 million in the 2025–26 season.

Though the moves disturbed the roster, the major goal was accomplished: becoming under the second apron.

Celtics Save $180 Million in Tax Penalties

With their back-to-back deals, the Celtics achieved speedy cap relief, ESPN front office insider Bobby Marks reported. He verified that Boston officially falls under the second apron, one of the most important lines in the NBA's new luxury tax model that severely punishes teams with inflated payrolls.

What Boston Gets in Return

The Celtics received Anfernee Simons, Georges Niang, and three second-round draft picks in return for their stars. Simons provides scoring punch and upside at guard, and Niang provides shooting and depth off the bench.

While neither Simons nor Niang offers the same defensive versatility as Holiday or the size and rim protection of Porziņģis, they come at a much more manageable price point. More importantly, their arrival reshapes Boston's roster with cap-friendly contracts, giving the team room to maneuver in the future.

Long-Term Flexibility Now in Focus for Celtics

The Celtics have obviously prioritized financial stability over immediate star power, a plan that can keep their championship window open while staying out of the league's worst penalties. These trades leave Boston set for greater flexibility in future free agency seasons, with room for maneuvering under the tax ceiling.

While fans will lament losing two name-brand contributors, William Chisholm knows the right strategy to make Boston a championship team once again. Instead of hanging onto a pricey roster, the Celtics realistically chose to rebuild in real-time while safeguarding their fiscal foundation.