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.

Injured Boston Celtics star Jayson Tatum will miss playing with Jrue Holiday in the backcourt and Kristaps Porziņģis helping out around the rim. Tatum sent parting messages to both players following Boston's trades with the Portland Trail Blazers and Atlanta Hawks.

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.