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 Boston Celtics have started their wheeling and dealing this offseason. ESPN's Shams Charania was the first to report that the Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons.

Anfernee Simons #1 of the Portland Trail Blazers drives to the basket against Payton Pritchard #11 of the Boston Celtics during the second half at TD Garden on March 05, 2025 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images) Getty Images