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 Blazers agreed to deal 26-year-old guard Anfernee Simons to the Celtics earlier this week, and the reasoning for the deal on Boston's side of the trade was about as clear as it gets. The Celtics were looking at one of the largest repeater tax bills in NBA history if they did not reduce salary on their 2024 title core.