Five Pointers

In 1927 Winifred Sheehan, Vice President and General Manager of Fox Studios, paid a visit to his old friend, Joe Brown (aka Joseph Castano), at Brown’s Place, an unmarked speakeasy/cabaret. Joe’s “jernt” was known only by its location, across from Earl Carroll’s Vanities, on 42nd Street. The speakeasy was the place where New York City’s elite could rub elbows with the underworld and experience a vicarious thrill. Thanks to the passage of the Eighteenth Amendment, constitutional prohibition created a new era of gangsters who were romanticized in the headlines. Hollywood was looking for a way to cash in on the gangster “popularity” and directors were clamoring for gangster material that could be incorporated into a movie script. This was the reason for Winifred’s visit to Brown’s Place. Why not go to his old source for the real lowdown on the underworld?Joe opened up his best bottle of Irish whiskey in deference to Winnie, an Irishman.

As they raised their glasses in a toast, Winnie told Joe that Hollywood needed his services.

“Whaddya mean?” said Joe.

“I have a job for you at Fox, telling the directors how gangsters act and playing yourself in a new movie, “Dressed To Kill.”

“You want me? Helluva way to earn the cakes!” replied Joe.

“You ought to know all about the thugs, how they act!” said Winnie.

Joe conferred with his bootlegging partner and pal, Owney Madden, and they both agreed, Joe should accept Winnie’s offer. In later years, Owney would go to Hollywood and rescue Joe from a possible gangland style slaying.

Winnie and Joe first met when Joe was a bartender at the Chatham Club on Doyers Street in Chinatown, around 1910.

Winnie was a reporter for The World and Joe would feed him colorful stories about the nightlife and other “activities” going on around New York City. Joe was careful to tone down his stories in order to avoid breaking “omerta” and incurring the wrath of his gangster pals. Years later, at his own cabaret and saloon “jernt”, The Old Mill, Joe would entertain other reporters with his stories. Both Walter Winchell and Herbert Asbury used Joe Brown as a source for information about the underworld.

Joe Brown (Joseph Castano) was born in 1883 to Nicola and Teresa Castano, immigrants from Naples, Italy. Joe was the second oldest out of 14 siblings and their “home” was located in the slums of Five Points. Nicola sold fancy cases (watches) for a living but did not earn enough “slugs” to “stoke up fourteen mouths.” The children supplemented their meager diet by “sneezing” (stealing) food, especially fruit. The Five Points area of New York City contained the worst slums in America. In order to survive slum life, Joe became part of the Five Pointers when he was around sixteen. By 1900 the Five Pointers were at their peak, with fifteen hundred members under the control of Paul Kelly (Paolo Vaccarelli). Paul Kelly used his New Brighton resort for planning various gang activities. The Five Pointers “earned” their money from gambling, prostitutes, Tammany Hall “political engagements”, and the operations of pickpockets, footpads, and loft burglars. The Five Pointers were in constant battle with the Eastmans, a rival gang composed of about twelve hundred warriors under the command of Monk Eastman. Click on The War Between New York Gang Chiefs: Monk Eastman and Paul Kelly.

In 1905, the members of the Five Pointers inner circle consisted of Paul Kelly (Paolo Vaccarelli), Frankie Yale (Francesco Uale), Joe Brown (Joseph Castano), Humpty Jackson, and Joe Casseli. A photo was taken to commemorate the allegiance they all had to each other.* The Five Pointers gang was one of the forerunners of the American Mafia and training camp for many of the twentieth century’s most notorious gangsters. Al Capone was brought into the Five Pointers by Frankie Yale and was very close to Joe Brown. This was the reason Capone’s favorite alias was Al Brown.

This material was written by Frances Carle(Asbury) and may not be published, broadcast, rewritten, copied or redistributed in any form without permission. Most of the background information was provided by Gregory J. Brown, grandson of Joe Brown. Gregory Brown also provided the photograph of Joe Brown. *A drawing based on a photograph taken of the original Five Pointers in 1905 will soon be added to the website.