The Blazers agreed to deal 26-year-old guard Anfernee Simons to the Celtics earlier this week, and the reasoning for the deal on Boston's side of the trade was about as clear as it gets. The Celtics were looking at one of the largest repeater tax bills in NBA history if they did not reduce salary on their 2024 title core.

The Celtics shipped the 35-year-old Holiday to the Portland Trail Blazers for the much-younger Anfernee Simons, and Holiday wasn't a fan of the move. Per Heavy Sports' Steve Bulpett, one source said Holiday is "pissed" about being traded to Portland.

He previously spent four days as a Trail Blazer after being traded by the Bucks and then acquired by the Celtics in 2023.