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.

On Monday night, they dealt Jrue Holiday to the Portland Trail Blazers in return for Anfernee Simons and a pair of second-round draft picks. Sources told MassLive that the picks include a 2030 selection from the Knicks and a 2031 pick from the Blazers.