The Boston Celtics’ offseason overhaul is underway after trading veteran guard Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two future second-round picks (2029, 2030). The deal, announced on Monday night, comes as a surprise move from a team heavily invested in retooling since their championship run in 2023.
The Celtics had made it clear that they would not be able to afford key players beyond the 2024-25 season due to an escalating payroll. However, coach Brad Stevens opted to sign nearly his entire rotation to extensions two years ago, making a strategic gamble on player value holding up despite aging. This move is now starting to pay off.
The Celtics took in $4.7 million in savings from trading Holiday and secured a more manageable salary cap hit for next year. Simons, who earns $27.6 million this season but lacks long-term money attached to him, could become an attractive player in secondary trades. The two second-round picks added to the deal will help replenish Boston’s draft cupboard.
Despite the Simons trade, Stevens’ work is far from over. Boston’s payroll remains above the luxury tax line, and further cost-cutting measures are inevitable. The Celtics are looking to retool while bringing spending back down to a sustainable level ahead of Jayson Tatum’s impending return.
With their off-season overhaul underway, the Celtics appear well-positioned for another strategic push under Stevens’ guidance.
Source: https://www.masslive.com/celtics/2025/06/brad-stevens-savvy-tactic-pays-dividends-with-anfernee-simons-trade-brian-robb.html