Joseph Cassano, Head of Financial Products at AIG
Cassano began his career at Drexel Burnam Lambert, under the tutelage of the junk bond king, Michael "A decade later and he'd have gotten away with it" Milken. AIG made billions underwriting and insuring complex multi-layer derivatives and securities…all of which, of course, were based upon nothing but the dreams of the ignorant and poor. Cassano told a few white lies, publicly stating he didn't think there'd be any loss, even though he did: "It is hard for us, without being flippant, to even see a scenario…that would see us losing one dollar." To his credit, they lost much more than one dollar, so there really was no reason to be flippant.
Cassano also routinely blocked internal and external audits of his unit, because, as all Unjailed Americans know, truth is the enemy of profit.
While taxpayers got the bill for bailing out AIG, Cassano walked away with over $300 million, plus a modest multi-million dollar severance package. Oh, and Cassano, he's not in jail.