Ironically, Holiday was briefly a Trail Blazer after his part in their deal with Milwaukee for Damian Lillard in 2023 before the Celtics acquired him less than a week later. Boston was lifting another trophy within the year, in no small part due to Holiday’s stout defense and unselfish team play.

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.

Jrue Holiday 'Pissed' Celtics Traded Him originally appeared on Athlon Sports. The Boston Celtics have agreed to trade two-time NBA champion Jrue Holiday to the Portland Trail Blazers. The Celtics are sending Holiday to the Trail Blazers for Anfernee Simons, a 2030 New York Knicks second-round pick and a 2031 Portland second-round pick.