I

In 1919, Al Capone had first arrived in Chicago from Brooklyn. He’d been sent there by Mafia boss Johnny Torrio, who wanted him to take over the rackets in the Windy City. The following year Prohibition was instituted across the United States, and Capone seized this opportunity to turn illicit booze into an empire. His home base was Cicero, a western suburb of Chicago, and prostitution rings, gambling, and bootleg-liquor operations were run from his headquarters in the Hawthorne Arms Hotel on Twenty-second Street. If Cicero had long been known for its buying and selling of police and politicians, the action inside the Hawthorne Arms solidified its reputation for Mob corruption. At the same time, clean cops were aggressively starting to pursue Capone and his gang. Five years after coming to Chicago, Capone got into a gun battle with the authorities on Cicero Avenue, which left his brother Frank dead.

John Robinson’s father, Henry, was eight when the violence erupted. The image of Frank Capone getting killed in the neighborhood—and then Al Capone repaying the favor the next year by dumping the corpse of Assistant State’s Attorney General William H. McSwiggin on a Cicero street corner—was extremely vivid in the memories of local people. They often talked about the bloodshed and spoke with awe of Capone’s headquarters, with its armed guards, metal windows, and impenetrable doors. Stories of the gangster and his crew were handed down from one Cicero generation to the next, part of a living oral history. On December 27, 1943, John Robinson entered a world where tales of legendary gangsters were common to every young boy.

In this neighborhood, having power and using it in illegal ways commanded respect. The streets were full of anecdotes about famous criminals who’d made up their own rules and lived by their own laws. Some locals admired those who could beat the system and make good money doing it, and a few old-timers regarded Capone as a hero. John Robinson heard these stories and absorbed them into his makeup, into his ideas about what was good and what was evil. He would not grow up to be a large boy or a strong one. He would not impress others with his physical prowess or good looks. As a youngster and later as an adult, he looked soft and round, friendly and harmless. If he was going to have power, he would have to find creative ways of getting it and using it. Al Capone had once said that you could go a lot further in life with a kind word and a gun than with just a kind word. Robinson only absorbed half of this adage—he would use kind words and smiles throughout his life to get what he wanted, but guns were not part of his routine. He didn’t need them in his line of work.

He grew up with four siblings: an older brother, Henry Jr., whom he did not like at all; a younger brother, Donald, of whom he was quite fond; and two sisters, JoAnn and Mary Ellen. He was much closer to JoAnn than to Mary Ellen (this swinging back and forth between intense personal likes and dislikes would mark him for life). The Robinson family lived in a well-kept but modest home at 4916 West Thirty-second Street. They drew little attention to themselves, and decades later, after Robinson became infamous, nobody in the neighborhood could even recall the people who’d once lived at this address. John’s father, Henry, worked as a machinist for Western Electric. When sober, he was a steady presence in the family, hardworking and law-abiding, totally unlike the gangsters from Cicero’s colorful past. From time to time, according to Robinson’s prison records, the older man went on bad drinking binges that disrupted everything. Despite this, his middle son had warm memories of him.

John did not feel that way about his mother, Alberta, who held the family together and kept the kids in line. When one of them misbehaved, she meted out the discipline and punishment. Five decades later, Robinson’s wife would testify to her coldness to John. Alberta demanded that her children be clean and neat, and she pushed them to better themselves. John seemed to respond to this prodding and was the most promising and ambitious of all the Robinson kids, the most eager to break out of their constraining blue-collar environment.

By thirteen, he’d channeled some of that ambition into becoming an Eagle Scout and was a senior patrol leader of Boy Scout Troop 259, sponsored by the Holy Name Society of Mary Queen of Heaven Roman Catholic Church in Chicago. A picture from that time shows a round-faced boy in his well-pressed Scout uniform; he’s offering a cherubic smile to the camera and giving a patriotic three-fingered salute. He’d recently been accepted into downtown Chicago’s renowned Quigley Preparatory Seminary for boys who were interested in becoming priests. He’d already told a number of people that he would eventually go to work in service to the Vatican.

A few weeks after making Eagle Scout, Robinson and 120 other Boy Scouts traveled to London to give a royal command performance for the newly crowned Queen Elizabeth II. Robinson, dressed in a bright red outfit, led all the others out onto the Palladium stage, becoming one of the first Americans to sing for Her Majesty and the youngest of his countrymen to appear at this acclaimed venue. The event made the front page of the Chicago Tribune, in an article headlined “Chicago Boy Scout Leads Troop to Sing for Queen.” His troop put on what they called “The Gang Show,” and after singing for the monarch, the boys gathered backstage to look at the celebrities who were also there to perform. When Judy Garland moved past him, Robinson boldly pursued her and caught up with the movie star, reaching out and shaking her hand.

“We Americans gotta stick together,” he told her.

“You’re right,” she said, laughing and kissing him on the cheek.

Another actress, the British singer Gracie Fields, hugged Robinson and told him, “You’re a mighty handsome youngster.”

The kid from Cicero loved the attention and being in the spotlight, but he soon returned to the seminary and quietly resumed his studies, still thinking of becoming a priest. He was a good student but not a great one. He wouldn’t be remembered there for his academic success but for his shrewdness: he always seemed to be thinking about what he would say or do next. He appeared to be calculating the effect he had on others and often acted as if he were smarter than everyone else. Yet he didn’t leave behind a negative image at the school. He graduated from Quigley at seventeen, not having distinguished himself at all.

Rumors had begun to surround Robinson suggesting that he was involved in a lot of things besides pursuing a religious education. Growing up in Cicero, he’d been exposed not only to stories of legendary gangsters but to people with ongoing connections to the Mob. He’d watched his father trudge off to the smokestacks at Western Electric each day and watched the older man labor tirelessly to support a family on a workingman’s wages. He’d watched his father seek escape from the grind in alcohol. By late adolescence Robinson knew that there were other, faster ways to turn a buck. His first exposure to crime came through meeting low-level underworld characters he did favors or legwork for, in exchange for money. By the close of his teenage years, his life had already become more complicated and entangled than it would have been on the narrow path toward the priesthood.

In 1961, he attended Cicero’s Morton Junior College, and in later years he would claim to have become a fully trained medical X-ray technician there. He would also brag about receiving more medical training at West Suburban Hospital in Oak Park, Illinois. With these limited credentials, he was able to land a job in the X-ray department of a Chicago hospital. His career was launched, but it was not a career in medicine.

In 1964, Robinson met an attractive young blonde named Nancy Jo Lynch and she was soon pregnant. They rushed into matrimony in a Catholic ceremony and he went back to work at the hospital. The young couple were starting a marital dance that would last through every imaginable kind of turmoil—and survive into the next millennium. From the beginning, they were locked together by mutual need, a need so deep that apparently nothing could break it. Robinson had avoided legal trouble, but almost as soon he got married, this changed. His living expenses were increasing and he was under pressure to take care of his wife and his about-to-arrive child. He didn’t respond to this by working harder or more hours. Before long, he was accused of stealing money from his employer.

Robinson’s marrying a pregnant woman had been an embarrassment to his family, but this was worse. The young man whose life had seemed so promising just a few years earlier, when he’d earned the title of Eagle Scout and sung for the queen of England, was on a downward spiral, but maybe he could learn from his mistakes and not repeat them. When confronted by his bosses with the suspicion that he’d embezzled from the hospital, he asked for their help, begged for another chance. If they would not tell the police about his transgressions, he would pay them back everything he’d taken. They agreed to this arrangement and he was not charged with a crime. What he’d learned from his mistakes was that he could get away with doing illegal things—even when he’d been caught doing them.