Joe Lieberman, Slum Lord

He is co-exeutor of his Uncle's estate ($25g/year for not doing much) and the properties in Stamford Connecticut that he was supposed to manage were dilapidated, garbage strewn, and occupied by squatters.

To be fair, he did eventually sell his uncle's property for $17 million, after he had arranged for millions of dollars in earmarks for the Stamford Urban Transitway, which increased the property's value.

What a prince.