On the evening of December 4, 1875, the notorious politician William “Boss” Tweed escaped a pair of prison guards in Manhattan and took off on an 11-month flight from justice across the United States, Cuba and Spain. The Tammany Hall leader had been sentenced to jail on charges of fraud, but before then he spent years rigging elections and skimming millions of dollars from New York City’s public coffers. Look back at the downfall of the man whose name has become synonymous with Gilded Age political corruption.

Even from behind bars, William Magear Tweed had found ways to game the system. While confined to New York’s Blackwell’s Island penitentiary in 1874, the man known as the “Boss” had used his privileged status to secure a transfer from a cramped cell to a private room with a window overlooking Manhattan. When he was later released and rearrested on civil charges, he was taken to the relatively plush Ludlow Street jail, where he bedded down in a two-room apartment and passed the time reading a small library of books. Tweed was allowed to receive visitors and pay a Ludlow employee to act as a personal aide. He even convinced the jail’s warden to occasionally let him leave the premises to visit relatives and take carriage rides through Central Park.

Tweed c.1870.

During one of his field trips on December 4, 1875, the former politician convinced his two guards to stop for dinner at his family home on Madison Avenue. Around 6:30 that evening, Tweed excused himself by saying he was going upstairs to check on his sick wife. Once out of sight, he grabbed his coat, snuck out the front door and hopped into a waiting carriage—a getaway vehicle that he’d secretly arranged by shelling out some $60,000. By the time his hapless jailers thought to check on him, the Boss was long gone. “I did not escape from the jail,” he later quipped, “but left my own house.”

In the years before he went on the lam, Boss Tweed had established himself as one of the most ruthless politicians in American history. He spent the 1860s serving as everything from a city supervisor to a state senator, but he was best known as the head honcho of Tammany Hall, the crooked political machine that dominated the Democratic Party in New York. “I don’t care who does the electing,” Tweed famously said, “so long as I get to do the nominating.” In an era when corruption was commonplace, the Boss and his “Tweed Ring” put their competitors to shame. They bribed judges and officials at will, rigged elections and wielded political influence like a weapon. The results were often positive—Tweed did a lot for New York’s immigrant poor and had a hand in creating both Central Park and the Brooklyn Bridge—but they also came with a hefty price tag. By falsifying government expenses and having contractors pad their bills on construction projects, he and his co-conspirators eventually lined their pockets with somewhere between $45 and $200 million in stolen city funds—the modern equivalent of as much as $2.4 billion. The 300-pound Tweed made little attempt to hide his ill-gotten gains. He bought huge amounts of property in Manhattan, dined in the city’s finest restaurants and took to wearing a 10-and-a-half carat diamond on his shirtfront.

Political cartoon by Thomas Nast depicting Boss Tweed with a money bag for a head entitled, “The brains that achieved the Tammany victory at the Rochester Democratic Convention.” (Credit: Kean Collection/Getty Images)

Tweed and his cronies seemed untouchable in the years after the Civil War, but by the early 1870s they found themselves under assault from the media. Harper’s Magazine’s Thomas Nast led the charge with a series of scathing political cartoons that turned Tweed into a citywide symbol of greed and graft. One drawing portrayed Tweed’s hulking frame with a bag of money in place of a head; another cast him as a vulture feeding on the bones of New York; still another showed the Boss’s thumb over Manhattan along with a caption reading, “Well, what are you going to do about it?” After a disgruntled Tammany operative turned over a cache of documents in 1871, the New York Times upped the ante with an exposé on the Tweed Ring’s financial swindling. The articles shed light on the massive cost overruns on a new courthouse, which included $360,000 in payments for just one month’s work from a Tweed-aligned carpenter. The accusations and investigations eventually piled up so high that even the Boss couldn’t wriggle out from under them. In late-1873, he was found guilty of 204 counts of fraud and sent to prison. Just two years later, he strode out the front door of his house and went on the run.

Boss Tweed never identified the individuals that helped engineer his escape, but the job was clearly well planned. After boarding his getaway carriage on the night of December 4, the 52-year-old was taken to the banks of the Hudson River and ferried by rowboat to Weehawken, New Jersey. Tweed spent the next several months hiding out in a secluded house in the woods. He adopted the alias “John Secor,” shaved his beard and began wearing a red wig and glasses to disguise his identity. In May 1876—two months after a civil court ruled that he owed the city $6 million—Tweed and his accomplices fled New Jersey for Staten Island, where they boarded a schooner and began a long voyage down the Atlantic coast. In Florida, the fugitive was handed off to a mysterious man calling himself William Hunt, who posed as his nephew during the rest of their journey.

Cartoonist Thomas Nast

Tweed and Hunt spent several days camping in the Everglades before catching a fishing boat to Cuba. They arrived in the city of Santiago de Cuba in June, but were immediately arrested by Cuba’s Spanish authorities for not having the proper visas. A description of the two suspicious travelers soon reached U.S. State Department. Guessing that “John Secor” was the fugitive Boss, Secretary of State Hamilton Fish sent word to the Cuban government asking for their cooperation in rounding him up. The locals agreed, but Tweed caught wind of the trap before it could close in. On July 27, he and Hunt stole away on a passenger boat bound for Spain.

Unfortunately for the Boss, his days as a free man were numbered. As his ship was making its six-week crossing of the Atlantic, Fish’s State Department sent a Navy warship in pursuit and telegraphed a warning to its consuls in Spain. When Tweed’s boat finally dropped anchor at the Spanish port of Vigo on September 6, 1876, the city’s governor was waiting on the dock to take him into custody. Fittingly, the Spaniards identified Tweed using one of Thomas Nast’s old Harper’s Magazine cartoons, which depicted the fugitive in a striped prison uniform.

Nast cartoon that Spanish authorities used to identify Tweed.

While his helper William Hunt was later released, Boss Tweed was turned over to the American authorities and shipped back to New York aboard the Navy frigate U.S.S. Franklin. His 11 months on the run had not agreed with him. He’d lost 100 pounds due to constant bouts of seasickness, and his hair and beard had turned snowy white. “I am an old man, greatly broken in health, cast down in spirit, and can no longer bear my burden,” he wrote after being returned to his old quarters at the Ludlow Street jail.

A demoralized Tweed would later agree to confess his crimes in exchange for a chance at freedom. Beginning in late-1877, he sang like a canary during several days of testimony before a special committee of the New York City Board of Aldermen. Among other acts of corruption, he admitted to fixing elections and siphoning off millions in city funds. He also provided a list of the contractors who’d colluded with him, and named the newspapers and journalists who’d accepted his bribes. The aging politician was widely praised for his mea culpa. A majority of the Board of Aldermen even called for his release, but former New York Governor Samuel J. Tilden and Attorney General Charles Fairchild backpedaled on a promise to set Tweed free. Following a final court appearance in March 1878, the nation’s most infamous politician was permanently banished to his rooms on Ludlow Street. He died just two weeks later at the age of 55.