10. Tweed was Ultimately Foiled by a Cartoon

Thomas Nast caricature of Boss Tweed in Harper’s Weekly, October 21, 1871. Image in public domain from Wikimedia Commons

Thomas Nast, basically the godfather of political cartoons, took an extreme disliking to Tweed, mocking his girth and love of money in a series of devastating cartoons. Tweed, who famously brushed of criticism from his political opponents (“What are you going to do about it?” was his mantra), lamented, “I don’t care a straw for your newspaper articles; my constituents don’t know how to read, but they can’t help seeing them damned pictures.”

After his conviction in 1873, Tweed was still permitted the occasional home visit. During one visit, he escaped out the back of his house and escaped across the ocean on a Spanish boat, posing as a fat, old sailor. At the Spanish border he was recognized by Floridian tourists on vacation, who’d seen his mug in a Nast cartoon. The authorities brought him back to New York, where he died in prison.

Tweed always believed other pols were just as crooked. While in prison, he received word that his sentence might be lifted in exchange for a confession, which led to a full revelation of his crimes. Unfortunately, Tilden and his associates would not honor that agreement.

Beyond the cartoons, Tweed also lives on in the Bad Book of Bill: Rogues, Rascals and Rapscallions Named William, Bill and Willie, by Lawrence Binda.

In case you were wondering whether New Yorkers were just duped dopes during the Tweed Era, keep in mind that it was the beginning of industrialization, and the City was doing very well. As historian Kenneth Ackerman puts it in Boss Tweed: The Corrupt Pol Who Conceived the Soul of Modern New York “It seemed like a great free ride, especially for the banks and brokerage houses making huge commissions on the bond sales. Tweed economics — borrow, spend and keep some for yourself — made sense to New Yorkers. Even the poor benefited.”

Next, check out the Top 10 Secrets of NYC’s City Hall building, just back to back with the Tweed Courthouse.