Jrue Holiday is now in his second stint with the Portland Trail Blazers after the Boston Celtics traded him to Portland before the NBA Draft. Of course, Holiday never played for the Blazers in his first stint.

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

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.