6. William “Boss” Tweed: Green-Wood Cemetery

As the leader of Tammany Hall, the unscrupulous Democratic political machine of the late 19th century, William “Boss” Tweed personifies corruption and avarice. During his reign, it is estimated that he and his political cronies stole over $200 million from the government, which is equivalent to $3.5 billion today. Boss Tweed ultimately ended up in prison in 1876 and died there from severe pneumonia in 1878.

While Boss Tweed was buried in Green-Wood Cemetery, the mayor of the time, Mayor Smith Ely, refused to fly the flag at half staff, not considering Boss Tweed worthy of the honor. As The New York Times reported in 1866, “It is the ambition of the New Yorker to live upon Fifth Avenue, take his airings in the [Central] Park and to sleep with his fathers in Green-Wood.”