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.

After falling short of capturing back-to-back titles, the Boston Celtics have gone through a complete makeover this offseason. As they continue to tinker with the roster, one mock trade surfaced where they address a key area of need.