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.

According to NBA insider Shams Charania of ESPN, the Boston Celtics could trade Anfernee Simons. The Celtics acquired Simons from the Portland Trail Blazers in the Jrue Holiday deal.  “I think players like Sam Hauser,

"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.