HOW DID RAFFLES GET THAT WAY ?
IT WAS a sweltering hot Tuesday in the middle of July in the Westchester County Court, White Plains, N.Y., when Judge Elbert T. Gallagher sentenced Gerard Graham (“Raffles”) Dennis to serve 18 years to life in Sing Sing Prison.
Dennis reddened, closed his eyes tightly for a moment, brushed aside his tears, walked quietly to his cell.
Thus ended the career of one of the most flamboyant lawbreakers of modern times. The little boy from St. Catharines, Ontario, who once pilfered pineapples from a fruit stand, had stolen a million dollars worth of jewels and furs.
A New York police chief called him “the greatest burglar who ever operated.”
What made Gerard Dennis run? Why did this handsome, clever young man choose the strange life of crime which has sent him to jail for the best years of his life? To find the answer hidden behind the flaming newspaper headlines I went down to the Niagara Peninsula, visited Dennis’ old haunts and talked to his friends and family.
To a social worker, one thing stands out in the case history of Gerard Dennis, this real-life Raffles, and that one thing is this: Dennis the man
differs very little from Dennis the boy and Dennis the youth. Even in his early years he was what he was on the day of his final arrest: handsome, charming, clever and crooked. It almost seems as if he had the Raffles mentality since he was barely able to toddle.
One of the earliest memories a friend of the family has of young Dennis is of him at one of his mother’s fashionable teas, hanging over the balcony, an angelic expression on his face, deftly swiping a cookie off each tray as they were being carried into the dining room.
Visitors at his trial were impressed by his appearance—his debonair grooming, expensive sharkskin suit, silk shirt and heavy cuff links (made from stolen gold). This was the same Dennis whose parents once combed every store in St. Catharines to find clothes stylish enough for him.
He was devilishly attractive to women— 5 ft. 10% in., 160 pounds, blue eyes, wavy chestnut hair. When the newspapers published the picture of Dennis, cigarette in lips, which appears on this page, the jailer in White Plains, N.Y., was swamped with letters from women all over the U. S., Canada and Mexico, containing extravagant amorous offers. Dennis had always prized his smooth complexion and clean good looks. As a teenager in St. Catharines he smeared olive oil on his face each night before bed.
As a boy he preferred the social pages to the comics. As a man he robbed the homes of socialites. In the summer of 1946 he took $64,000 in loot from four homes on Long Island. In six months his Hollywood loot included $15,000 from songwriter Max Gordon, $20,180 from Loretta Young, $257,775 from socialite Thomas R. Winans.
He planned his burglaries carefully, reading the social columns, visiting night clubs, studying gems and furs from displays and library books. He secured aerial photos of places to be robbed. He kept notes on the habits of Louis B. Mayer, Mrs. Henry J. Kaiser Jr., and Lady Thelma Furness. When arrested he was carrying a list of victims-tobe. They ranged all the way from Jack Benny to Hedy Lamarr.
As a lad in his middle teens Dennis was a favorite with older folk in St. Catharines who found him polite and considerate—always ready with a chair, a hand to carry parcels, or help with an overcoat.
Just as the twig is bent ... At 17 (below) Dennis was already a thief in police files. At 29 (right) he had stolen a million and earned a scholarship to Sing Sing. The boy who pinched pineapples went on to diamonds, mink, and the end of the road.
Gerard Dennis stole women’s hearts and a million in jewels and furs on his inevitable journey to jail. Here’s how his fate was forged
When he robbed Charles Leff at gunpoint of $8,000 he promised to leave Leff’s car intact after using it as a getaway. He kept the promise. When he robbed the home of Mrs. T. H. Lewis and heard she was Loretta Young he remarked. “I would never have done that if I’d known. She’s my favorite star.” He withdrew from one large estate when he found it belonged to Bing Crosby whom he also admired.
Even in his early teens Dennis was interested in beautiful women. Significantly they all seemed to follow a set pattern: they were young, fresh-
looking, extraordinarily attractive, unsophisticated and strictly brought up.
Gertrude, his first wife, whom he married when he was 19, came from a small town near St. Catharines and was regarded as a local beauty. She circumvented her parents by meeting Dennis when she was supposed to be taking music lessons in Welland. He deserted her and his two children after a few years of marriage. Yet today she says, “Apart from the one twist in his mind he was one of the finfest men I’ve ever met.”
Dennis’ second serious attachment was a girl named Eleanor Harris whom he met in a Toronto war plant. Several times she attempted to leave him but always returned. She lived with him in Montreal and later in New York under assumed names. Then in August, 1947 Dennis skipped out of his apartment one step ahead of the police. He never returned to see either Eleanor or their child. Eleanor, now remarried, still says, “Life with him was exciting, interesting and tense.”
When arrested last February Dennis was living with Betty Ritchie, an exToronto schoolteacher, in a luxurious Beverly Hills apartment. She knew him as Jerry McKay, businessman and inventor. “He was the most wonderful of husbands,” said Betty. “He was thoughtful, considerate, always asking if there was anything he could do for me. Even the little things like helping me with the dishes, going shopping with me so I wouldn’t have to carry heavy bundles.”
Ironically, it was a beautiful woman who hastened Dennis’ downfall. In New York he induced Gloria Howard, a pretty model, to sell jewelry for him. She didn’t know it was stolen. When police caught her in Philadelphia trying to dispose of blue-white diamonds set in platinum Dennis vanished. Angry and bitter, she was to spend the next year and a half helping police track down the man who had deceived her.
Even with a parole Gerard Dennis will be 43 when he gets out of Sing Sing. To many who knew him well his life has been tragically wasted. He was handsome, pleasing and clever.
“He was so intelligent,” said Gloria Howard. “I’m convinced he could have made as much money legitimately.” Others have often said this about him.
Why did he turn out this way? Was he alone responsible? Would u have been possible at any stage in his criminal career to have reformed him?
Many efforts were made to discourage his delinquent behavior. When he was a schoolboy his mother and teachers tried to keep him out of trouble. Between the ages of 10-14 before he was ever charged with a crime, social workers and police spent hours appealing to him. At various times, his father, stepmother, brother, sister, wife and girl friends encouraged him to lead a respectable life. They failed.
“He was bad through and through,” says police Inspector James Anderson of *St. Catharines. “He had every chance in life but threw them all away.”
. . . These Tragic Circumstances
One could perhaps explain Dennis by comparing his actions to those of a psychopathic personality. This type is a riddle even to psychiatrists. Outwardly the psychopath is sane and intelligent. Yet he is driven by mysterious impulses to deceive, lie, and steal. He is without conscience. Right or wrong don’t concern him. He doesn’t respond to treatment, nor does he learn by experience. He can’t settle down to a conventional job, has no qualms about not supporting his own family, and blames other people for his troubles. At the right moment he may pretend to be sorry for all he’s done but he doesn’t mean a word of it.
Dennis’ version of why he is a criminal may be summarized as follows: He was a normal child until he was eight. Then his father was sent to prison. His friends taunted him,
shunned him. At 14, his parents were divorced. For 13 years he had neither home nor parents. His lawyer pleaded, “Under these pathetic and tragic circumstances, is it any wonder he became a delinquent?”
There is truth in this. But on the other hand, Dennis tells only part of the story of his background. It doesn’t wholly jibe with the facts as I found them on my visit to St. Catharines.
Gerard Graham Dennis was born on April 15, 1920, in Homer, a tiny town near St. Catharines. A few years after his birth his family moved to town where his father was an accountant and auditor. Gerard was the youngest of three children.
His father, Joseph Dennis, was a thin-faced, moustached, partially deaf Englishman. In 1913 Julia Cronin came over from England to marry him. People recall her as a talkative, nervous woman, given to dressing in a somewhat dramatic and eccentric fashion, but, nonetheless, in excellent taste. She was an accomplished singer who had given up a career with the D’OylyCarte Opera Company to come to Canada. One woman says of her, “She was somewhat arty and aloof. She was the sort of woman one always called JuliaA rather than Julie.”
Dennis was an exceptionally beautiful and charming child. His boyhood home was on Wellington Street in a staid and respectable residential district made up of spacious houses, each with its own well-kept lawn and garden. It is set amid a half dozen churches, the Convent of St. Joseph, the YMCA, and the Public Library.
A Rakeoff in Pineapples
There were persistent rumors that Mr. and Mrs. Dennis were incompatible, but no open sign of rift. The family “belonged” in St. Catharines society and the three children were invited to all the birthday parties and picnics. Mrs. Dennis frequently entertained at tea.
“When Gerry was eight,” says Julia Dennis, “I was left to bring up the three children myself. We were always poor. Gerry was shunned and taunted by the other children. He was a very sensitive boy and I believe his father and childhood influenced him greatly.”
But there are other stories told of this period. True, the family didn’t have nearly the same amount of money to spend, but in many ways life went on very much as before for the children. They were still invited to all the parties and the children of the neighborhood still went over to their home to play.
“The only difference was,” recalls one playmate of that time, “that I was warned in advance not to ask where poppa was. There were children in St. Catharines I was not allowed to play with but Gerard Dennis wasn’t one of them.”
At eight Gerry Dennis teamed up with other youngsters to pilfer fruit and vegetables from local fruit stands. Dennis was the master mind of the gang and collected a rakeoff. Once the gang stole eight pineapples. Dennis’ commission was two pineapples. At this time he was an altar boy in the church.
When he was 10 he invited one of his friends up to his bedroom and removed a plank from the floor. There, in a secret hiding place, rested a real revolver and a Tarzan outfit made of genuine leopard skin. He never explained where he got them.
Although not charged in court till he was 14, Dennis was always in trouble after the age of 10. At St. Nicholas school the teachers couldn’t manage him. Neither could Mrs. Dennis. She would come down to the police station and urge Inspector Anderson (then a detective) to talk to the lad. “I’m worried,” she would say. “I don’t know what’s going to happen to that boy.”
Once Anderson went up to Dennis’ room and found all kinds of loot in his secret hiding places. There were guns, revolvers, rings, watches, dentists’ and doctors’ instruments, cameras and knives. One of those knives still rests in the top drawer of Anderson’s desk. If is a seven-inch homemade stiletto with a plastic and metal handle*
Like most kids Dennis liked to take the watches apart. He would also carefully remove precious stones from rings, earrings and pendants and then explain that he had “lost them” or that “they fell out.” Significantly, when he was finally apprehended on February 16, 1949, he was trying to sell $75,000 worth of loose diamonds which had been pried out of their settings.
Rather than haul him to court, the police, social workers and judges all took turns trying to get young Gerry Dennis to mend his ways. They found him well-mannered and polite. “He would listen very attentively,” says Anderson, “taking it all in. But it never did any good.”
He was not as well behaved to his mother. He would often interrupt her as if trying to head off her conversation. Once, when she threatened to call in the police, he held her off at the point of a dagger.
By this time he had grown into a good-looking schoolboy with a clear complexion and regular features. He liked beautiful things, especially things he could feel. He was fond of music.
Despite his popularity he was a lone wolf, a boy no one really got to know. He was regarded as “a deep thinking boy” and spent much of his time by himself. Boys’ clubs or sports held little interest for him.
He was fastidious about his appearance and had a distaste for dirtying his hands. He would spend hours filing his finger nails until the tips were smooth and rounded.
Many of the school kids his age spent some of their time after school hanging out at a local ice-cream parlor. Not Dennis. Instead, police found him wandering through the wealthy residential district, carefully examining large homes. He was already known as a person who was “in and out of everybody’s house.”
lie Loved Beautiful Things
It is significant that visitors to the Dennis home, at this time, recall that he lived in a strongly feminine environment. The home seemed dominated by Mrs. Dennis and her numerous music pupils, mostly women. Boys learn about the outside world from their fathers, how to get along with other men, how to compete with them.
Perhaps the fatherless home helps to explain the Dennis enigma.
“He was feminine in taste,” says a lifelong woman friend. “He loved good grooming, good living, and beautiful things. He felt that he was an exciting, exquisite creature and that the world owed him a living. He expected the world’s riches would be handed to him on a diamond-studded platter. When life didn’t turn out that way, he chose an exciting and easy way to get what he wanted.
“Much of Gerry’s success with women was his feminine understanding of them. And he knew enough to consistently choose inexperienced women who would not be put off by his masculine lack of character.”
In January, 1934, just liefere he was 14, Dennis was caught with a supply
of sporting goods stolen from the Wentworth Radio and Auto Supplies on St. Paul Street. As he was so often to do in the future he readily admitted his guilt. Police and social workers discussed the matter with his mother and it was decided to bring him to the juvenile court. “It may bring him to his senses,” they agreed.
Judge J. S. Campbell wanted the young man strapped and Mrs. Dennis, whose permission was legally necessary, agreed. But later she changed her mind and Dennis was released with a warning.
Eight months later he was back again charged by his mother with incorrigibility. He received a long lecture from the judge who told him to report back in a week for sentencing. But when that time came, Dennis was hundreds of miles away.
This was only one of many mysterious trips he was to take away from home. He would go without warning, never write home, and return unexpectedly without a clue about where he had been. Later the police threw some light on these excursions. Once, for example, he had been to a Muskoka resort looting parked cars and cottages. One of his hauls was a complete set of dentistry tools. No one ever claimed them from the police.
He Scoffed at the School
By 1934 Joseph Dennis was reestablishing himself in St. Catharines where he lives quietly today. He and his wife had been in constant friction and finally agreed to separate. Julia Dennis packed and prepared to leave for England with her daughter.
Gerard Dennis later claimed he overheard his mother planning to put him in a home. “Rather than submit to this,” he said, “I ran away, sleeping in cellars and lots, finally in the attic of a rooming house where my father lived.”
According to his father this is a rather fanciful version of what actually happened. “Shortly after his mother left for England in 1934,” says Joseph Dennis, “I remarried earlier than I had intended so my two sons would have a home. My present wife and I made a good home for them.” They lived in a well-kept seven-room stucco house.
In the fall of 1935 Dennis registered at the St. Catharines Collegiate Institute. He was a poor student. His Christmas examination average was 43. His best mark was 66 in English composition, his worst 14 in sheet metal theory.
He scoffed at school rules and couldn’t get along with teachers. During a shop period he lost his head and “told off” the instructor. He was allowed to stay in school after apologizing but was finally expelled for misconduct one month before the end of the school year. That was the end of his formal education.
He had never been one of the school crowd. He belonged to no clubs or athletic teams. He remained a stranger among his fellows with a reputation for being in and out of everybody’s locker.
But the girls adored him. One girl friend recalls, “He made you feel that you were the only woman in the world. I could have pictured myself running away with him if he wanted me to.”
He frequently skipped school to take his girl for long walks along the Welland Canal. He talked seriously about what he wanted of life. He had a normal desire to travel. Not so natural was his desire for expensive jewelry, crystal ware and tapestries. He wanted these things not only for their beauty but for what they represented.
His girl remembers that he spent
much of his time thinking up ways of fooling people. Once he outlined a scheme for beating a hotel bill by checking in with a piece of phony luggage. He told her how he could shake off pursuing police by making a soap-box speech and escaping in the confusion. Another time, as they walked along a beach, he bet her that he could break into the next three boathouses. He won his bet.
Dennis often told her how much he cared for his mother in England (she stayed there till 1948) and how much he disliked living with his father and stepmother. He said that they were strict and never gave him anything he needed. Yet, when the girl accepted an invitation to dine at the Dennis home, she found the Dennis family pleasant and the home atmosphere relaxed.
“Always a Soft Spot for Gerry”
If Dennis really cared for his mother he didn’t show it. Unlike his elder brother he had to be reminded constantly to write to her and send her cards on her birthdays. Could it be that his aversion to his father and stepmother was due to his complete inability to accept guidance and discipline of any sort? It is only natural that a thwarted adolescent should reason, “Things would be far different if my real mother were here . . .”
After his expulsion from school at 15 Dennis continued to see his girl who lived at Niagara-on-the-Lake. He was independent by nature. When broke he walked the 12 miles rather than borrow bus fare. Once when he had a job picking berries nearby, his girl’s family invited him to stay at their house. Dennis refused, preferring to pitch a tent and live by himself. It was even with great reluctance that he accepted an invitation to stay for a meal.
As usually happened, there was a division of feeling about him in his girl friend’s family. Her mother adored him. Her father disliked him.
Once he gave his girl a diamondstudded wrist watch saying it was a keepsake from his mother. Not long after the police took it away from her. It had been stolen only a few weeks before. That was the end of their relationship.
Yet even today that girl confesses, “I’ll always have a soft spot in my heart for him.”
Between the ages of 16 and 21 Gerry Dennis pursued an active criminal career. In 1936, found guilty of several charges of theft in Brockville, Ont., he was sentenced to several months in the reformatory. He told police his name was James Graham Martin, explaining later, “I didn’t want to disgrace my folks.”
The next year he pleaded guilty to eight charges in Toronto and St. Catharines of being in possession of burglar tools, housebreaking and theft. He was given one year at Guelph Reformatory. In March, 1941 the Ontario Provincial Police slapped eight charges against him for breaking into summer cottages around St. Catharines. He was sentenced to prison for two years less a day.
Between trips and prison sentences Dennis continued to live at home. Here he was pleasant, helpful and honest. His stepmother frequently left her money and jewels around. They were never touched.
He was more careful than ever about his appearance. Brushing his hair, filing his nails, examining his eyebrows were serious, leisurely rituals.
Dennis often looked too smooth. Once at a dance near St. Catharines somebody objected to his zooty appearpearance, especially his king-sized hat. A fight ensued. In the first few seconds Dennis was given a black eye and might have received even worse had the fracas not been broken up by a number of his girl friends who “just couldn’t stand seeing poor Gerry being hurt.”
Dennis in his late teens was still no “joiner.” Unlike his brother, he rarely went to church. He used to say, “It’s a lot of baloney.” He spent hours in his room at home sitting and thinking.
Dennis had a number of jobs hut none of them appealed to him. For a time he ushered at a downtown theatre from 6 to II p.m. As a precaution, his father made it a rule that he should he home in bed by midnight. Dennis usually stuck to the rule, hut after his parents were asleep he would sneak out of the house. Other times, he would pay someone to take his place at the theatre while he went about his other activities. When these substitutions became too frequent he was fired.
His father asked him to work with him. “I took him in with me at a time when work was short and I was trying to build up my auditing business,” Joseph Dennis recalls. “I told him, ‘You do the books at home, I’ll drum up the business and do the outside work. I’ll give you 50% of everything we make.’ ”
He Loved Them, and Left Them
Young Dennis had an aptitude for figures and the arrangement ran smoothly for a few months. Then he grew restless and dissatisfied. He told his father, “You’re a sucker. You’ll work till you have humps on your head and never make real money. I’m going to make my pile an easier way.”
He disappeared and the next thing his family heard he was in trouble with the police. Joseph Dennis took his son back into business a number of times, only to have him return to criminal activities.
“1 did everything I could for him,” the father says, tears welling up.
Dennis treated the women he loved in a puzzling and contradictory fashion. His behavior towards them followed a pattern. He would woo them ardently, lx? exceedingly devoted and attentive for a time, then suddenly run off leaving them penniless. No woman’s love ever inspired him to change his ways.
His relationship with women corresponded in a curious fashion to his relationship with his mother who had left him behind when she went to England in 1934. Perhaps the lack of a close relationship with his mother
the prototype of all women—resulted in his unconscious avoidance of a close, lasting relationship with any woman.
Gerard Dennis married his first wife, Gertrude, while she was still in her teens. She was infatuated with him. To her the marriage was a perpetual honeymoon. But it lasted only 10 months—until Dennis was arrested. She waited a year until his release from prison and again life was “wonderful.” Then one day he walked out of her life forever. At the time, she had two children under two years of age.
He drifted to Toronto and worked in a war plant where the women promptly nicknamed him “lover hoy.” For his special attention he singled out Eleanor, a timekeeper whom reporters have described as “quick, graceful and vivacious, as trim as a movie starlet, as appealing as a lullaby.” This alliance ended in New York in 1947 when Dennis went into hiding from police.
Three weeks later he wrote Eleanor’s lawyer a remarkable letter in which he absolved her of all guilt and heaped abuse upon himself. “I successfully deceived and lied to my wife and family,” he wrote, in part. “I have similarly disgraced a previous wife and two children and am now causing misery and disgrace to another. I realize with disgust the extent of my sins . . .”
Before long a series of spectacular thefts tipped police that Dennis was in California. Here, with brown-haired Betty Ritchie, he lived a quiet life, usually eating in their apartment and going to movies, concerts, and museums in the evening.
Apart from Dennis’ expensive clothes and car there were no extravagances. They both wanted a good phonograph to play records but Dennis said they couldn’t afford it. Betty was given $15 a week for food, nothing for extras.
When she went to live with him she had $400 in the bank of her own money; when he was arrested nine months later she was penniless.
When the law finally caught up with Dennis in Cleveland on February 16, 1949, he ran true to pattern. He readily confessed to his crimes as well as to a number he had planned for the future. Whisked to the east coast, he was just as obliging.
“As we refresh his memory,” said one of his interrogators, “he admits he did each job. All we have to do is supply him with some of the details.” He spent a whole day driving around New York with police, showing them where he disposed of his loot.
He appeared chastened. Detective Lieutenant Maurice P. Kelley, of the New Rochelle police, said, “He has shown repentance. He has twice broken down and cried like a baby when he’s realized how he’s disgraced his family in St. Catharines.” At one point, Dennis asked the police, “Can’t you fellows all get together so that I
can do my 20 or 30 years and pay my debt to society.”
After making a long statement one afternoon, he announced: “My mind
is free of a lot of things that were bothering me. Iam happy that now I can talk freely to ease my conscience.”
When a lawyer told him that he resembled movie star Robert Taylor, he replied sadly, “I might have been better off if I didn’t.”
Mrs. Dennis (Gerard’s mother), who shares a fiat with her daughter in St. Catharines, is today a white-haired woman, her lined face bearing marks of sorrow. She still gives music lessons.
Gould He Have Been Saved?
“I find it hard to talk about Gerry,” she told me when I saw her recently. “I read the papers, afraid of what might come to light about him next. What he did is fantastic, utterly fantastic. I just don’t understand it.”
Most people don’t understand it. To understand fully the forces which shaped Gerard Dennis from birth into a real-life Raffles would take long and exhaustive study by a qualified expert in human behavior. In this case history I have simply pieced together the tragic jigsaw of Dennis’ life and the answer to the enigma is in the fabric of this story.
A boy with a record like Gerard Dennis should have been sent to an institution like the Ontario Training School for Boys at Bowmanville and Galt. These schools have none of the marks of a prison. They provide a boy with a mental, moral, physical and vocational education. In this healthy atmosphere most youngsters strive for success and lose interest in antisocial ways.
If Dennis was a psychopathic personality he would have required an even more intensive type of training and supervision. Such training is available at a boy’s institution maintained by New York State, the Annex of the State Training School for Boys, but there is no institution of exactly this type in Canada.
The population of this school is limited to 50 boys. A full program of work and play is carried on with great emphasis placed on the teaching of social relationships. Teachers never handle more than six or seven boys at once so that they can study them closely. Of 69 entrants treated, 20 boys, half of them diagnosed as psychopathic, have been paroled. Only one has had to be returned to the school.
Would such a school have saved Gerard Graham Dennis? Maybe, maybe not. The young man gripping Sing Sing’s bars and peering at the muddy Hudson will never know. But his wasted life, the heartbreak he caused, are a challenge to all of us.