The Prototype for Citi Bike Was Invented By Monk Eastman, A Pigeon-Loving Gangster From Williamsburg


Earlier this month, Citi Bike announced that its bike renters had taken over 5 million rides. And while they’re certainly the biggest name in the bike rental game today, if they were operating 100 years ago, they’d have some stiff competition from Monk Eastman, an eccentric Brooklyn-born gangster who ran one of the earliest, most successful bike shares in the city’s history, when he wasn’t busy hoarding animals, beating people up, or smoking copious amounts of opium.

Eastman was reputedly born Edward Osterman in Williamsburg, Brooklyn around 1873 (although some accounts contend he was born in Corlear’s Hook, now a park area on the Lower East Side). He loved cats and pigeons, so much so that his father, a Jewish restaurant owner, helped set him up with his own pet shop.

But the pet store game failed to excite him, and he left in the mid-1890s to become a bouncer (or “sheriff”, as they were then known) at the mammoth New Irving Dance Hall. Eastman sounds like he was a real looker in his prime, according to a description of him in Low Life, Luc Sante’s classic book about the seedy underbelly of turn-of-the-century New York:


Unlike his fellow gangsters of the time, Eastman was so crude in appearance that he could model for the stereotypical crook who has continued to show up in cartoons down to the present day (he had a bullet-shaped head, a broken nose, cauliflower ears, prominently throbbing veins, numerous knife scars, pendulous jowls, and a bull neck, and was usually seen wearing an undershirt, with a small derby perched on the back of his head of longish, unkempt hair.

Eastman ran a number of gangs; The Eastmans were first, named after him, and with a headquarters in a saloon on Chrystie Street. As he grew more powerful, he also started keeping pigeons, five hundred of them, by several estimates, as well as more than a hundred cats. He opened another pet shop on Broome Street, which doubled as a front for his less-lawful activities. Other gangs that answered to him during that time were the McCarthys, the Cherry Street Gang, the Fourteenth Street Gang, the Lolly Meyers, the Red Onions, and the Yakey Yakes. But most importantly, for our purposes, there were the Squab Wheelmen, run by a gentleman named Crazy Butch.

At some point, Eastman acquired a bike shop too; according to Herbert Asbury’s 1928 Gangs of New York (from whence the movie came), the Squab Wheelmen were all required to rent a bike from there once a week. They rented the bike, Asbury writes, “whether they knew how to ride or not.”

An April 1912 issue of Pearson’s Magazine confirms that story; in an article called “Apaches of New York,” G. W. Dillingham writes that the bike rental doubled as a way to move up in Butch’s gang:

Those who thirsted to stand well with him, were sedulous to ride a bike. They rented these uneasy engines of Eastman, with a view of drawing to themselves that leader’s favor. Butch, himself, was early astride a bicycle. One time and another he paid into Eastman’s hands the proceeds of many a sklush or or schlam job; and all for the calf-developing privilege of pedalling about the streets.

For Crazy Butch, the bikes also doubled as another handy aid to criminal activity. Several accounts describe a scam where Butch would ride headlong into someone, preferably a woman, knocking her over. He’d hop off the bike and start a screaming argument with the lady; as a curious crowd started to form around them, Butch’s boys would pick their pockets.

Things went swiftly south for Eastman in 1904, when he was caught rifling through the pockets of a passed-out drunk near 42nd Street and Broadway. The lush turned out to be a wealthy young man; two detectives were tailing him to keep him out of trouble. Eastman had been wanted for years, and this last slip-up was enough, finally, to send him to Sing Sing. (There’s no record of what became of his cats or his pigeons after he was put away; one has to assume the worst.)

Eastman was sentenced to ten years but got out in five, only to find that the entire landscape of the Lower East Side had shifted. His army of thugs had all either died or been absorbed into other gangs. He’d lost his place, although, as Sante notes, he did manage to organize the rag-pickers who worked at the East River dump into a union “and lead them in a bloody strike.”

But in 1912 he was picked up again while smoking opium and did eight months in prison; almost as soon as he got out again, he was picked up for robbery and did three more years. In 1917, when he was 43 years old, he joined the National Guard, for some reason, went to France and became a war hero. His citizenship had long been revoked due to his felony convictions, but Governor Al Smith restored it after his fellow soldiers wrote a petition in Eastman’s favor.

Despite that patriotic interlude, things didn’t end well for Eastman; in 1920, two days after Christmas, he was found shot to death one morning on Fourteenth Street. He’d spent the night at the Bluebird Cafe with a group of shady characters, including Jerry Bohan, a crooked Prohibition agent. Around 4 a.m., the two men started arguing, and Bohan took out a pistol and shot Eastman down.

Eastman was buried with full military honors; a crowd of 10,000 people turned out to watch him go. If you’d like to tip your hat to the father of modern bike rental, Eastman is buried at Cypress Hills Cemetery in Brooklyn. If you can find him, that is; his grave is unmarked.

The full report on Eastman’s murder, from the December 27, 1920 edition of the New York Times, is on the following page.

Monk Eastman Murder