Allan Houston: 6 years, $100.4 million (2001)
A deal that was such a horror show that the NBA came up with it’s own rule — in his namesake — to correct itself. In 2001, the New York Knicks signed Allan Houston to a six-year, $100.4 million contract extension. Coupled with subsequent injuries, his $20M+ salary per year made him the most toxic asset for any team to consider in the NBA.
In 2005, the NBA agreed on a new collective bargaining agreement (CBA), where the NBA effectively allowed one team to amnesty one contract from their salary cap ledger (although they’d still have to pay that player); that rule is commonly referred to as “the Allan Houston rule.”