On a cold, gray winter morning in 1933, when Stanley Shaw was not yet four years old, his mother brought him and his older brother Sol to the Brooklyn Hebrew Orphan Asylum. They would be under the supervision of the asylum until the summer of 1939, and as Shaw writes in this moving memoir, "I have spent tremendous energy during much of my life both embracing and fleeing from those six and a half years, simultaneously trying to remember and forget them, but invariably trying to solve the mystery of what brought me there."

What brought him to that lonely Castle on the Hill was the breakup of his parents’ marriage. His father Louie was a hard-working man who also happened to be a compulsive gambler. Left alone without any money, his mother Ida was unable to care for her children, so after farming out her oldest boy Eli to her rich relatives in Long Island, she brought Stanley and Sol to the orphanage.

During the Depression it was not unusual for children with living parents to become wards of the BHOA. The youngest children, like Stanley and Sol, were placed in foster homes, and Stanley’s experience with his foster parents ran the gamut from loving idyll to a nightmare out of Charles Dickens. His last placement was so grim he convinced Ida and Louie to give their marriage another try, a moment that today Shaw considers the first deal he ever made in what would become a lifetime of deal-making.

Once reunited, the family endured a series of trials that would haunt the Shaw brothers for the rest of their lives. Yet Stanley found his first taste of freedom on the streets of Depression-era Brooklyn, moving through a world of poolroom hustlers, bookies, gamblers, loansharks, and schoolyard friends.

After working his way through Columbia University and New York Law School, Shaw married and established a small law practice, only to find himself in business with a real-estate developer who proved to be one of the more outlandish characters in recent memory. At the end of their association, Shaw was in debt to the tune of one million dollars.

Depending on his wife Doris to hold their family together, Stanley Shaw continued to build his law practice. By then, he was immersed in Liberal Party politics, and his political career brought him into contact with the luminaries of the day: Governor Nelson Rockefeller; the Honorable Arthur Goldberg; Senator George McGovern; Mayor John Lindsay; and a host of others who trotted across the national stage. Before Shaw was finished with politics he had led a renegade faction in a battle with Alex Rose—the tall, broad-shouldered father of New York’s Liberal Party and a legendary city boss whose power ran all the way to the White House. The war culminated in Shaw’s candidacy for mayor of New York.

As his frontline political career drew to a close, Shaw was asked to look into the financial problems of the Bohack supermarket chain, and suddenly he was in the midst of a colossal five-year struggle that would become, at that time, one of the largest bankruptcy cases ever filed in the Eastern District of New York.