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.

What should we make of the trade of vet Boston Celtics guard Jrue Holiday for Portland Trail Blazers guard Anfernee Simons? The deal, which saw the Celtics agree to send Holiday to the Blazers for Simons and a pair of second round draft picks,

After officially sending Anfernee Simons to the Celtics, the Trail Blazers would be wise to re-route Jrue Holiday for even more value.