7. Tweed and his Ring May Have Stolen as Much as $200 Million from New York City

We’re not talking about just landing a contract for a buddy, or sneaking an appropriation into the budget. Depending on your metric, $200 million in 1871 is worth many billions of dollars in today’s money, and it was used to line the pockets of Tweed’s Ring. Other members of the ring include “Elegant” Abraham Oaks Hall, a dapper prototype for future Tammany Mayor “Gentleman” Jimmy Walker (he also served as counsel to Mayor Fernando Wood, infamous for his motion that Manhattan should secede from the Union). Hall ran into problems when his mishandling of a religious parade led to a Irish Catholic v. Irish Protestant brawl that killed 62 people. The brains of the operation was Parks Commissioner Peter Sweeney, whose schemes are reminscent of Office Space‘s Michael Bolton. The Comptroller was “Slippery Dick” Connolly. Enough said.

These four men trusted each other little, and the Ring’s self-destruction was a question of if, not when. When the relatively young New York Times began invesitgating this story in the summer of 1871, Tammany was only mildly threatened – at one point they tried to buy out the paper to kill the story. But publisher George Jones would not sell, and the shocking revelations of theft, lies and greed led to a full investigation.