A few key figures largely controlled politics in the 19th century. Among them, William Magear Tweed was a well-known politician in his time. He was often called Boss or Boss Tweed, a name derived from his other moniker, William Marcy Tweed. Mr. Boss was the leader of Tammy Hall, a political party that played a crucial role in the politics of the day. William Tweed was an astute but crooked man who owned vast wealth, including large tracts of land.

On December 4, 1875, Mr. Tweed made headlines after escaping prison; this was after he was found guilty of embezzling funds from state and city contracts. The money he stole amounted to millions of dollars, earning him twelve years in prison. Unfortunately for the justice system, Mr. Tweed was a man of his means and soon got his sentence reduced to one year. His life behind bars was no ordinary life. He furnished his cell with luxury furniture and organized a library in his room to keep him busy.

Shortly after his release, however, Mr. Tweed was arrested to face more charges. His subsequent sentence was to be carried out in Ludlow Jail. This was when he made his attempt to free himself. His taste of independence did not last long as he was briefly arrested after fleeing from Cuba to Spain. After he was re-arrested, Mr. Tweed faced civil charges in addition to his escape. He was unfortunate enough to spend the rest of his life in prison, passing away in 1878.