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 acquired Anfernee Simons as part of the Jrue Holiday trade, but the veteran guard may be on the move yet again.

The Boston Celtics are sending veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks.