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Authors: Pete Hamill
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restriction on personal liberty, which it was,
and doomed to lead to widespread corruption, which it did. Many agreed with the New York madam Polly Adler, who said about
enforcing these invincibly stupid laws: “They might as well try to dry up the Atlantic with a post office blotter.” Madams,
alas, know more about human nature than do ministers. In New York City on the eve of Prohibition, there were 15,000 places
where a man could get legally drunk; within a few years there were 32,000 speakeasies providing the same service in defiance
of the law. The same phenomenon was true in New Jersey. And Dolly Sinatra was to open her own speakeasy on the corner of Fourth
Street and Jefferson in Hoboken. She called it Marty O’Brien’s.
“It was supposed to be a restaurant,” Sinatra remembered. “And you could get some pasta there, or a sandwich. But it was really
a saloon. She didn’t call it Mama Sinatra’s, remember; she called it Marty O’Brien’s. You’re Irish: would you go to a place
called Marty O’Brien’s for the
food?
”
Years later, while delivering the Libby Zion lecture at Yale Law School, Sinatra remembered that his father worked for a while
for the early bootleggers, who made their runs north to Canada to pick up shipments of whiskey. (My father took a few similar
runs himself, to the depots of Lake George.) As a prizefighter, even a mediocre one, Marty Sinatra would be a natural form
of muscle.
“He was one of the tough guys,” Sinatra recalled. “His job was to follow trucks with booze so that they weren’t hijacked.
I was only three or four, but I remember in the middle of the night I heard sounds, crying and wailing. I think my old man
was a little slow, and he got hit on the head. Somebody opened up his head, and he came home and was bleeding all over the
kitchen floor. My mother was hysterical. After that, he got out of that business. They opened a saloon.”
Dolly Sinatra was able to run that saloon because of her political connections. She was naturally gregarious, full of spirit
and jokes, equipped with a bawdy sense of humor. That made her a perfect bartender. But it was her political talents that
gave her the freedom to run the place itself. She spoke the natural, rushed American English of the New York area, which allowed
her to communicate easily with the Irish political bosses. She had mastered a number of Italian dialects, which made her a
perfect go-between in the neighborhood between baffled individuals and the agents of the state. She knew how to get a lawyer
or a tax accountant or a bailbondsman. She showed up at weddings and wakes. She was generous with her personal time, repeatedly
helping those neighbors who were less fortunate than the Sinatras. But she was also a realist. She had learned how the world
works and looked at it clearly. Niccolò Machiavelli, the philosopher of political lucidity, would have loved Dolly Sinatra.
Yes, there was a part of her that wanted the world to be better, an idealistic streak that would reach fruition during the
New Deal. But in the days of Prohibition, she was more concerned with living in the world as it was. And prospering in it.
That obviously meant knowing some of the bootleggers. Not all were Italian. The Mob was not a synonym for the Mafia. It was
an alliance of Jews, Italians, and a few Irishmen, some of them brilliant, who organized the supply, and often the production,
of liquor during the thirteen years, ten months, and nineteen days of Prohibition. The most famous of the original Mob chieftains
were Lucky Luciano, Meyer Lansky, Ben (Bugsy) Siegel, Frank Costello, and Longie Zwillman. Their alliance – sometimes called
the Combination but never the Mafia – was part of the urgent process of Americanizing crime. (Sinatra, in my conversations
with him, sometimes employed the word
Mob
when referring to the gangsters of the era but usually called them “the boys.”) The
and doomed to lead to widespread corruption, which it did. Many agreed with the New York madam Polly Adler, who said about
enforcing these invincibly stupid laws: “They might as well try to dry up the Atlantic with a post office blotter.” Madams,
alas, know more about human nature than do ministers. In New York City on the eve of Prohibition, there were 15,000 places
where a man could get legally drunk; within a few years there were 32,000 speakeasies providing the same service in defiance
of the law. The same phenomenon was true in New Jersey. And Dolly Sinatra was to open her own speakeasy on the corner of Fourth
Street and Jefferson in Hoboken. She called it Marty O’Brien’s.
“It was supposed to be a restaurant,” Sinatra remembered. “And you could get some pasta there, or a sandwich. But it was really
a saloon. She didn’t call it Mama Sinatra’s, remember; she called it Marty O’Brien’s. You’re Irish: would you go to a place
called Marty O’Brien’s for the
food?
”
Years later, while delivering the Libby Zion lecture at Yale Law School, Sinatra remembered that his father worked for a while
for the early bootleggers, who made their runs north to Canada to pick up shipments of whiskey. (My father took a few similar
runs himself, to the depots of Lake George.) As a prizefighter, even a mediocre one, Marty Sinatra would be a natural form
of muscle.
“He was one of the tough guys,” Sinatra recalled. “His job was to follow trucks with booze so that they weren’t hijacked.
I was only three or four, but I remember in the middle of the night I heard sounds, crying and wailing. I think my old man
was a little slow, and he got hit on the head. Somebody opened up his head, and he came home and was bleeding all over the
kitchen floor. My mother was hysterical. After that, he got out of that business. They opened a saloon.”
Dolly Sinatra was able to run that saloon because of her political connections. She was naturally gregarious, full of spirit
and jokes, equipped with a bawdy sense of humor. That made her a perfect bartender. But it was her political talents that
gave her the freedom to run the place itself. She spoke the natural, rushed American English of the New York area, which allowed
her to communicate easily with the Irish political bosses. She had mastered a number of Italian dialects, which made her a
perfect go-between in the neighborhood between baffled individuals and the agents of the state. She knew how to get a lawyer
or a tax accountant or a bailbondsman. She showed up at weddings and wakes. She was generous with her personal time, repeatedly
helping those neighbors who were less fortunate than the Sinatras. But she was also a realist. She had learned how the world
works and looked at it clearly. Niccolò Machiavelli, the philosopher of political lucidity, would have loved Dolly Sinatra.
Yes, there was a part of her that wanted the world to be better, an idealistic streak that would reach fruition during the
New Deal. But in the days of Prohibition, she was more concerned with living in the world as it was. And prospering in it.
That obviously meant knowing some of the bootleggers. Not all were Italian. The Mob was not a synonym for the Mafia. It was
an alliance of Jews, Italians, and a few Irishmen, some of them brilliant, who organized the supply, and often the production,
of liquor during the thirteen years, ten months, and nineteen days of Prohibition. The most famous of the original Mob chieftains
were Lucky Luciano, Meyer Lansky, Ben (Bugsy) Siegel, Frank Costello, and Longie Zwillman. Their alliance – sometimes called
the Combination but never the Mafia – was part of the urgent process of Americanizing crime. (Sinatra, in my conversations
with him, sometimes employed the word
Mob
when referring to the gangsters of the era but usually called them “the boys.”) The
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