3. Isiah Thomas
Zeke is responsible for a good chunk of this list. Jerome James? Steve Francis? Eddy Curry? Take your pick. Dolan should've noticed that Thomas ran the CBA into the ground due to over-spending, but no, he still hired him as President of Basketball Operations. For some odd reason, the Knicks had high hopes with Isiah making all the basketball decisions, but those same hopes soon turned into a nightmare five years too long. He was applauded when he brought Starbury back home, hired Lenny Wilkens, and made the playoffs in his first year. The "success" of his first year on the job was short-lived. New York got off to a slow start during the 2004-2005 season and Lenny was replaced by assistant Herb Williams. Herb was replaced the next year with another Hall of Fame coach by the name of Larry Brown. Zeke signed Larry to a record breaking deal, giving him $10 million a year for five seasons. During Larry's first and only year, the Knicks went 29-59 and teamed up Marbury with Steve Francis (lmao). Brown was fired and replaced by Thomas.
That didn't change much as the Knicks continued to struggle. Unbelievably, James Dolan decided to give Isiah an extension in 2007 amidst a sexual harassment lawsuit by a former employee. It was over after that. Thomas acquired Z-Bo and his enormous contract while signing Jerome James and Jared Jeffries to ridiculous contracts putting the Knicks deeper in debt. Then again, perhaps decision-making isn't the chief quality of a dude who threw his own daughter under the bus.