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 Celtics shipped the 35-year-old Holiday to the Portland Trail Blazers for the much-younger Anfernee Simons, and Holiday wasn't a fan of the move. Per Heavy Sports' Steve Bulpett, one source said Holiday is "pissed" about being traded to Portland.

He previously spent four days as a Trail Blazer after being traded by the Bucks and then acquired by the Celtics in 2023.