Winchell was born near the corner of New York's Madison Avenue and 166th Street, a Harlem slum neighborhood. His parents, Jacob and Janette Bakst Winchel, were poor Russian Jewish immigrants. (Winchell later added the second l to the family name following a theatrical misspelling.) Jacob Winchel opened and closed several hole-in-the-wall shops on upper Broadway in an attempt to earn a living; defeated, he turned to playing pinochle and left the burden of supporting the family to Janette. After a series of separations and reconciliations, Jacob finally deserted his wife and two sons. Winchell's home life was erratic and unhappy. Often he and his younger brother, Albert, were boarded out with strangers or sent to stay with their grandmother, who ran a candy store, while their mother undertook a variety of jobs. Whenever they could, other relatives pitched in to help Janette keep the family together. Winchell became a streetsmart gang leader, and by the age of ten he was channeling his energy into gang fights and moneymaking chores.
Winchell was bored and rebellious in school. He played hookey to hawk newspapers and to indulge in his favorite pastime, vaudeville shows.
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