4. The Larry Brown Saga
On July 28th, 2005, James Dolan gave Larry Brown the richest contract in NBA history for a head coach $50-$60 million for five years. The team finished 23-59 in Brown’s first season. After feuds with Stephon Marbury fueled the turmoil, Dolan made the decision to fire Brown after one season. It would come at a cost though as Brown was bought out for $18 million and additionally paid $10 million for the one season he coached. Essentially, James Dolan paid Larry Brown a lump sum of $28 million for one of the worst seasons in Knicks history.