Jerry Krause and Scottie Pippen
Everybody knows that Krause was one of the greediest, conniving general managers in basketball history. He infamously manipulated Pippen into one of the most one-sided contracts in NBA history. Remember, Pippen was one of the league’s best players and a key cog in their ’90s dynasty.
Pippen’s team advised him not to take the deal that saw him receive almost 17 million dollars across six years. This affected his relationship with the GM and owner Jerry Reinsdorf before he finally joined the Rockets. But ironically it also gave the Bulls more financial freedom to build a roster around him and Jordan (via CBS Sports).