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 trading Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks in the first major trade since the end of the NBA Finals. It's a fairly rare trade in that the recent champion Celtics are giving away the well-known veteran while the younger rebuilding team is giving away young talent in a win-now effort.