In many ways it seemed like William Tweed had it made. He was the boss of one of the most powerful political machines in the history of New York, and possibly the United States. He and his political underlings had arranged to keep large swaths of the public coffers at their personal disposal through graft and patronage. Their takings are estimated at a minimum of $1 billion in today’s money. Some estimates go as high as $8 billion.

Although Tweed would hold only a handful of high profile offices in his life, as an alderman and later as a commissioner he would engineer massive overpayments to contractors and companies that he owned or were owned by his friends and allies. Tammany Hall seemed to be in an unassailable position astride the New York City economy, gorging itself on public money and keeping many dependent on the money they doled out. But in the space of just a year or two a coalition of city fathers, turncoats and one unlikely character artist would break Tammany Hall’s power and leave it flailing for relevance in the new political landscape.

Doomed by Cartoon, by John Adler, tells the tale of Harper’s Weekly and Thomas Nast as they set out to call out and bring down Tweed and his ring.

Thomas Nast is not a well known name today, but many aspects of his work are now irrevocable parts of the American consciousness. Among other things, he created the modern image of Santa Clause and the association of the Republican Party with the elephant. He also helped to popularize the images of Columbia (America personified as statuesque Greco-Roman woman bearing sword and shield), Uncle Sam (Nast is credited with adding the goatee) and the Democratic donkey.

But few of his accomplishments equal the significance of his stand against Tammany Hall (although he is credited with being a deciding factor in the election of Grover Cleveland as well). The contrast between Tweed and Nast is stark. One was a big man, the other small. One was a wealthy man of far reaching influence in business, the other was a very poor business man and had little influence beyond beyond being a goad in public policy. In many ways, it was a bit of an American David and Goliath battle.

But Nast did far surpass Tweed in one respect, and that was his ability to influence people. While Tweed’s methods were usually straight forward bribes and blatant corruption that couldn’t be proved only because he was holding all the cards, Nast leveraged humor, cultural touchstones and memorable images into a platform that goaded his opponents to distraction.

While it’s fair to say that there were far more factors at work in Tweed’s downfall than Nast – inside information, a timely riot, news exposes in other papers – it was Nast’s constant attacks in Harper’s Weekly that kept the issue before the people. Tweed himself acknowledged Nast’s influence when he said, “I don’t give a straw for your newspaper articles; my constituents don’t know how to read, but they can’t help seeing them damned pictures.”

In fact, attempts would be made to bribe Nast into leaving the country for a while, with offers of half a million dollars (worth considerably more then than now) being made. But in the end Nast stayed in New York Tweed went to jail. In an ironic coda, when Tweed escaped a few years later and made his way to Spain by boat, the Spanish police would identify and arrest him using a Nast cartoon as a reference.

It’s actually a rather straightforward political story, in as much as political stories can be straightforward, but what makes Doomed by Cartoon unique is that it includes over 160 Nast illustrations, giving them context and pointing out the ways many of them tie into the events of the Tweed era. As an amateur artist and a student of politics I found it very interesting. Maybe you will too.