Trail Blazers general manager Joe Cronin received criticism when Portland acquired Jrue Holiday from the Boston Celtics this past offseason. Holiday is a clear upgrade over Anfernee Simons from both a talent and impact on winning standpoint, even at this stage in his career. However, many still questioned why a rebuilding Blazers team made an aggressive win-now trade.
There were concerns surrounding Holiday's contract, age, and injury history. He's currently the highest-paid player on Portland's roster, owed $32.4 million this season with a $37.2 million player option in 2027-28 -- at which point he'll be 37.
Unfortunately, we even saw some downsides to that risk when the Blazers' aging star missed roughly two months with a lingering calf strain.