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.

This NBA offseason isn't waiting around for the draft to get rolling. Heck, the Kevin Durant trade went down before the Finals even ended. And one day after Game 7, ESPN's Shams Charania broke the news that the Boston Celtics were dealing Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks.

"Anfernee Simons is a BETTER player than Jrue Holiday, 9 years younger, making less money, and on an expiring deal," Moran said. "Blazers just gave the Celtics an out on Jrue's horrible contract." Holiday's contract, signed in 2024, was worth $135 million over four years.