Celtics ultimately traded Holiday to Portland in exchange for Anfernee Simons and two second-round draft picks.

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.

Boston will also receive two second-round draft picks in exchange for Holiday, a six-time member of the NBA's All-Defensive Team and a key part of the Celtics' run to their most recent NBA title