Anfernee Simons was an obvious trade candidate for Portland this past offseason, but the expectation was that the rebuilding Trail Blazers would move Simons in exchange for future assets. General manager Joe Cronin took the opposite approach, swapping Simons for a 35-year-old Jrue Holiday with the Boston Celtics.
That shocking and aggressive move received criticism from the start. Question marks surrounded Holiday's fit with Portland's timeline and his $104 million owed over the next three seasons, which many deemed to be an overpay due to his declining play in Boston.
But it took less than ten games with the Blazers for Holiday to shift the narrative.