New York has had its share of corrupt politicians. But few cast as depraved a shadow as William M. “Boss” Tweed.

How brazen was Tweed? As head of Democratic political organization Tammany Hall, he passed a new city charter in 1870 that gave him control of the city treasury.

That allowed Tweed and his cronies to embezzle tens of millions of dollars, mostly by creating fake contracts, padding bills, and invoicing the city for services never rendered.

After an outcry on the part of The New York Times and Harper’s cartoonist Thomas Nast (below, one of his infamous illustrations of Tweed), he was tried and convicted of fraud and larceny charges in 1873.

He should have been locked up for life. But a year later, his sentence was reduced from 12 years to one.

After his release from prison on Blackwell’s Island, he was rearrested on civil charges and sent to the Ludlow Street Jail—a relatively cushy prison for white-collar criminals.

Now here’s the really ballsy part. Because the Ludlow Street Jail was so accommodating, they allowed Tweed to take carriage rides in Central Park and visit his family at their Madison Avenue mansion (with a prison guard in tow).

During one visit in December 1875, Tweed disappeared. He took off and fled the city.

Where did he go? First to New Jersey, then Florida, and then to Cuba. From there he made his way to Vigo, Spain.

However, the Spanish recognized him from a Nast cartoon and notified New York officials—who had offered a $10,000 reward for information about his whereabouts.

“When asked about his flight, Tweed said that some friends urged him to go to Turkey or to Egypt, where the telegraph could not so easily locate him,” wrote The New York Times, “but he finally picked Spain, hoping that in the absence of an extradition treaty the Spanish authorities would not surrender him.”

No such luck. He was sent back to the city, and a year later, in 1876, was again incarcerated on Ludlow Street.

This time, he wasn’t allowed daily family visits. He confessed his crimes in an attempt to win freedom, but he was convicted of nonpayment of a civil judgment and kept in jail.

He died there, on Ludlow Street, at age 55 in 1878.

Read more about Tweed’s crazy web of corruption in New York City in the Gilded Age, in bookstores and on Amazon starting on June 3. [Ludlow Street prison photo: New York Times]

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Tags: Blackwell's Island prison, Boss Tweed escapes prison, corrupt politicians New York City, Ludlow Street Jail, most daring prison escapes, Tammany Hall corruption, Thomas Nast, William M. Boss Tweed