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

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.

Who won the trade that sent Jrue Holiday to the Portland Trail Blazers for Anfernee Simons, the Boston Celtics or the Portland Trail Blazers? The Blazers get a future Hall of Fame guard to bolster their already formidable defense,