He stole up to $200 million from New York City in broad daylight — and was finally brought down not by investigators, but by a cartoonist whose drawings his illiterate constituents could actually read.
William 'Boss' Tweed ran New York City's Tammany Hall political machine in the 1860s and early 1870s, and during his peak he essentially was New York City. He controlled the mayor's office, the courts, the state legislature, and the city treasury — funneling contracts through allies who padded their bills by five, ten, or even a hundred times, then splitting the overpayment among the ring.
The scale of the theft was staggering. The construction of the New York County Courthouse — budgeted at $250,000 — eventually cost nearly $13 million. One carpenter was paid $360,751 for a single month of work in a building with almost no woodwork. A plasterer received $133,187 for two days of labor. Tweed personally owned the marble quarry supplying the courthouse. Historians estimate the ring stole between $25 million and $200 million in total — equivalent to several billion dollars today.
Tweed was finally undone by a cartoonist. Thomas Nast's savage caricatures in Harper's Weekly depicted Tweed as a grotesquely fat vulture and a crown-wearing thief. Tweed reportedly offered Nast $500,000 to stop — and when asked why the cartoons worried him more than newspaper articles, Tweed said: 'My constituents don't know how to read, but they can't help seeing them damned pictures.' The New York Times was offered $5 million to suppress its own investigation and refused.
Tweed's escape from prison is one of the more surreal chapters in American political history. While serving time in Ludlow Street Jail, he was allowed supervised home visits. During one such visit in 1875, he simply walked out and fled — by boat to Cuba, then to Spain, where he worked as a common sailor. U.S. authorities tracked him down and had him arrested at the Spanish border — reportedly identified by Spanish officials using Thomas Nast's cartoons, which had circulated internationally.
Despite the spectacular corruption, Tweed was genuinely popular with New York's immigrant poor. He funded churches, hospitals, orphanages, and schools across religious lines — at a time when Protestant institutions systematically excluded Irish Catholics. He distributed food and cash during hard winters, and his Tammany precinct workers showed up at weddings, funerals, and fires. Critics who painted him purely as a villain missed why so many voters kept electing him.
Tweed died in prison in 1878 — broke, broken, and betrayed. He had struck a deal to testify against his ring in exchange for release, but the governor refused to honor it. New York's mayor refused to lower City Hall's flag to half-staff when he died. He was buried in Brooklyn's Green-Wood Cemetery. The courthouse his ring built — one of the most extravagantly looted construction projects in American history — still stands today as New York's Tweed Courthouse.