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.

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.