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 Boston Celtics are trading Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, according to ESPN's Shams Charania. The deal marks the se

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