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 Portland Trail Blazers have ended Anfernee Simons ’ seven-year run with the franchise by trading him to the Boston Celtics for Jrue Holiday. ESPN’s Shams Charania first reported the news. Simons, 26, averaged 19.3 points and 4.8 assists last season while struggling to adapt to being the starting point guard.

"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.