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.

A late-night trade saw Jrue Holiday traded to Portland from Boston for Anferenee Simons. Here's how both teams made out.