Why Red Ryan’s shadow still hangs over every prison yard

With nineteen convictions, lifer Red Ryan turned altar boy. So they set him free—and he went on the gory binge that left us with one of the Western world’s most backward parole systems

TED HONDERICH December 7 1957

Why Red Ryan’s shadow still hangs over every prison yard

With nineteen convictions, lifer Red Ryan turned altar boy. So they set him free—and he went on the gory binge that left us with one of the Western world’s most backward parole systems

TED HONDERICH December 7 1957

Why Red Ryan’s shadow still hangs over every prison yard


With nineteen convictions, lifer Red Ryan turned altar boy. So they set him free—and he went on the gory binge that left us with one of the Western world’s most backward parole systems


Prisoner K.-166, his denims changed for a new' brown suit, walked beside a guard to the great north gate of Kingston Penitentiary. Convicts exercising in the yard cheered him on. Red Ryan, the armed bandit of a hundred headlines, passed quietly through the gate and across the road to the warden’s office. It was late afternoon, July 24, 1935; a grey Wednesday. After eleven.and a half years of a life sentence, served with saintly piety, the bank robber who belatedly became an altar boy w'as returning to freedom.

The warden handed him a ticket of leave. It had been sought long and fervently by a handful of partisans, and finally granted through the personal intervention of Prime Minister R. B. Bennett. Although he had a record of nineteen convictions progressing from bicycle theft to armed bank robbery, Ryan was legally leaving Kingston's w'hite walls behind. Over these same walls he and four other convicts had once clambered after starting a barn fire and wounding the chief keeper with a pitch fork, a chore Ryan took care of personally. Now the penitentiary was wishing him luck.

On this day the curtain rose on the final act of a tragicomedy that left Canada with one of the most backward parole systems in the western world.

Until he was shot dead by a policeman ten months later. Ryan led two lives. In public he was the gentle man who had been an orderly at Kingston Penitentiary’s hospital, the ingenious tinkerer who had invented a lock for prison mailbags, and the pious altar boy of the penitentiary's Roman Catholic chapel. At the same time he was robbing and murdering.

The exposure of Canada’s most celebrated paroled convict as an unregenerate killer so shook the country that it discredited demands

for new and more humane methods of rehabilitating criminals. As a result thousands of men and women who have since broken society’s rules have suffered from the evils of antiquated penal regulations. No other single event has done so much to hold back penal reform in Canada as the fateful freeing of Red Ryan.

His parole had been opposed by the officials who knew him best. Several days before he was released the director of sentence remissions in the Department of Justice spoke against setting Ryan free. But through “benevolent” interference his parole was secured. And today, two decades later, Ryan is still cited as proof that it would be folly to adopt a more humane parole system modeled on those of Britain and the Ú. S.

Norman John (Red) Ryan w'as born on July 18, 1895, in Toronto, the fourth of eight chilli ren. His father was a law-abiding laborer. At twelve Ryan w'as convicted of stealing a bicycle; a year later he went to reform school for stealing chickens.

One day during this auguring boyhood a gang of boys was playing with a new football on Euclid Avenue. The ball belonged to Eddie Murphy, who had been taken to St. Francis parochial school on his first day by Norman Ryan. The brash, freckled redhead grabbed the ball and carried it off. Fifteen years later Norman Ryan stood shackled in a Toronto court, facing a life sentence for bank robbery. One of the crown attorneys was E. J. Murphy, the onetime owner of the stolen football.

When he was seventeen Ryan was sentenced to three years in Kingston Penitentiary for burglary. theft and shopbreaking; and another six months for shooting with intent to maim. He was serving a second term in Kingston, twelve years for a payroll robbery and several lesser

offences, w hiLf World War I broke out. Two years later lj***is released to become a soldier. Overseas, time in the army lock-up at

Seaford, ir-'^V/ • ' for robbing stores and going absent Jj^^T^eave. After several escapes from militJpr. ’ /ÊL Ryan deserted England and the Arm yW * • rc h a n t Navy. In 1921 he

returned tiÇ’ Toronto.

Back hiR’nic he Ijv*J with his brothers and

sisters at 7>?>yWsfcam Street, became a tinsmith

and married. Between August and December

of 1921 a lone gunmar held up five Hamilton

and Montreal banks. *n December, his wife

already left behind, Ryan was arrested in Mont-

real. He was sentenced to twenty-five years in

Kingston Penitentiary, but his stay was to last

only a year.

continued on page 76

continued from page 28

The American papers called him “the

Jesse James of Canada”

At ten o’clock one morning in September 1923, the straw-filled prison barn burst into flame. A long-awaited wind billowed smoke over the wall, cutting off the vision of a nearby tower guard. Five men dashed from the barn, carrying a long board into which spikes had been driven. Four of them scurried up the wall on the makeshift ladder: Edward McMullen, Thomas Bryans, Gordon Simpson and Andrew Sullivan. Chief Keeper Matthew Walsh arrived and Ryan, guarding the retreat with a pitchfork, struck him in the right thigh before departing. A week later Matthew Walsh received a letter from Ryan. “He said he was sorry for having had to use the fork,” Walsh recalls. “And he kind of praised me for what I had done in trying to stop the break.”

Twelve days after the break three armed men walked into the Bank of Nova Scotia at St. Clair and Oakwood in Toronto. The loot was $3,107; Ryan was eventually convicted of this robbery. While police bustled to suspected hide-outs, Ryan and Andrew Sullivan crossed the border and began a scries of bank robberies, perhaps five, in the United States. They eventually settled in Minneapolis, which was something of a resort for criminals in the 1920's. From there they visited the Grand Avenue State Bank in St. Paul, which provided five thousand dollars. Ryan communicated continually with friends and relatives in Canada by mail and by the personal column of an American magazine called Detective, which featured mug shots of wanted criminals. His letters were intercepted. Three months after

his escape detectives waited for him in the Minneapolis main post office. Wounded in the shoulder during a gunfight, he surrendered. As he was being led outside, Sullivan began shooting from a parked automobile. Ryan failed to get away in the melee, but Sullivan did; a uniformed policeman and two bystanders were wounded. Police learned Sullivan had been seeing a waitress and he was killed on her front porch the following day.

Seized upon by the Hcarst press as “the Jesse James of Canada” and promoted with similar gusto by a number of Canadian newspapers, Ryan gained mounting notoriety. For the rest of his life he courted publicity. In Minneapolis he disappointed few reporters. One paper even printed the story that he had once escaped from the Tower of I.ondon.

He arrived back in Toronto shackled hand and foot and handcuffed to Detective William Meehan, of Minneapolis, who had wounded him and killed Sullivan. A crowd waited at the station with the reporters and photographers. They saw a tall muscular twenty-eightyear-old wearing a belted overcoat with a black-edged bullet hole in the shoulder. A fourteen-man escort took him to police headquarters and a reporter who saw him in a corridor wrote: “One wondered how so seemingly mild and gentlemanly an individual could have got himself in such a predicament.” The story these lines are taken from appeared the same day Ryan pulled a hacksaw blade out of the bandage on his shoulder. Then he traded the blade to

the guards in return for a steak dinner.

He was tried by Judge Emerson Coatsworth for the Toronto bank robbery that had taken place twelve days after he broke out of Kingston Penitentiary. The trial started at 10:10 a.m.; exactly two hours later he was on a train back to Kingston facing a life sentence and thirty strokes. In handing down the sentence the judge said, “If you turn around and make a complete change in your mode of life and become a model prisoner . . the future is

very largely in your hands.” Ryan must have listened well.

According to his autobiography he was kept in a half-underground cell block called “the hole” for his first eight months at Kingston. During those months he met his personal savior, the Rev. Dr. Wilfred T. Kingsley, the Roman Catholic chaplain who was priest of the Church of the Good Thief in nearby Portsmouth.

Partly through the chaplain’s influence Ryan was allowed, about two years after he arrived, to go to work. He shook out mailbags in the yard, mended them, and repaired the locks and metal parts. Later, when his release was pending, a Toronto doctor who had served a Kingston sentence wrote a book in which he referred to Ryan in the yard: “There he stood, a perfect physical specimen. He was as different from the story-book criminal as the rosy dawn differs from the blackness of midnight. I am reminded of the description of David of sacred history. ‘Now he was ruddy and withal of a beautiful countenance and goodly to look to.’” If not precisely a David, Ryan

was obviously a very captivating fellow.

From the time he went to work. K-166 was the model prisoner mentioned by Judge Coatsworth. These were the days of stringent oppressiveness in the penitentiary. There was the lock-step and the rule of absolute silence; but Ryan kept himself submissive and well behaved.

In November, 1926, the Toronto Globe carried a story about Ryan and his theftproof lock. Widely reprinted, it was no doubt the first influence in arousing public sympathy for “Canada’s Jesse James.” Ryan the tinsmith had invented a lock for mailbags. “Even Ryan himself cannot pick them,” declared the Globe. One of the locks was forwarded by penitentiary officials to the Ottawa post-office department. It could be picked with a nail and was never manufactured, but newspaper stories on Ryan from 1926 on mentioned the lock as being in service in the post offices of Canada.

The year after the lock story Ryan was back in the news. The Ottawa Journal claimed he was using a cache of one hundred and twenty thousand dollars to help his sister in her struggle with tuberculosis. Two years later the Toronto Mail appeared with a story headed, “Famous bandit proves tender nurse in prison.” Ryan had been made an orderly in the prison hospital. He swept floors, fed sick inmates, administered some medicines, took temperatures, made beds and even assisted as a scrub nurse in the prison operating room.

By 1930, K-166 had become even more than a model prisoner. He was at one time Father Kingsley’s altar boy at mass in the chapel. He read biographies of great Canadian statesmen while writing his own. He constructed crucifixes inside light bulbs and molded images of the Blessed Virgin. No longer smoking or swearing, he advised young inmates on “the straight and narrow.”

About 1931 Father Kingsley began to work actively to secure Ryan’s release, visiting Ottawa and writing innumerable letters. His was the initiative but he found allies. One was Col. H. A. Mullins, a Conservative M.P. and later a senator. Mullins saw Ryan in the penitentiary and went to talk to Prime Minister R. B. Bennett and Hugh Guthrie, then Minister of Justice.

Favorable newspaper publicity rolled on. “I want to carry a dinner pail,” Ryan was quoted. Judge Fred Weegar, of North Bay, Ontario, declared he should be given a job lecturing to wayward boys in reformatories. Ryan was educating himself and had asked an enlightened fellow inmate to explain Einstein’s theory of relativity. Finally Judge Emerson Coatsworth, who had sentenced Ryan to life imprisonment, rebuked a lawyer who happened to refer to him as a "hardened criminal.” The judge said he understood Ryan had become “a very estimable citizen.”

But against the Ryan partisans were a number of persons concerned directly with prisoner releases and K-166. Justice Minister Guthrie was opposed to granting Ryan his freedom. M. R. Gallagher, at that time director of remission service, was firmly against it. Richard Allen, then warden of Kingston Penitentiary, was critical of it.

In 1932 Norman Ryan petitioned for ticket of leive. Although in that year he added to his reputation by staying out of riots in the prison, he was refused. Father Kingsley and his band took up their cause a year later. Ryan, who wrote fairly good English, sent drafts of suggested letters to his brother who used them in bombarding the governor-general, members of parliament and anyone

else who might be useful. As a result of more approaches to the prime minister, Ryan received a well-publicized, halfhour visit from Bennett on July 24, 1934. The conversation was no doubt replete with assurances of purification.

In a personal letter to the Ryan family after his visit, Bennett wrote, “I was greatly impressed by what he said to me ... I can only say that his demeanor, his clothes, his sleeping cot and surroundings were calculated to stimulate him to renewed efforts for usefulness. The minister charged with responsibility in such matters is at the moment absent. When he returns I will speak to him about this matter.”

Ryan’s younger sister died in Weston Sanitarium in July 1935. The prime minister was telegraphed a request and K-166 appeared in Toronto for the funeral with an unarmed guard. After seeing part of a movie, he returned docilely to Kingston. About this time Jack Corcoran, a prosperous and respected wrestling promoter in Toronto, was approached by Father Kingsley. “I had never known Norman or his family,” Corcoran recalls. “But I was recommended by someone and Father Kingsley wanted me to advise Norman and get him a job.”

At the time, Corcoran owned the Ncalon Hotel on King Street, a lively establishment with singing waiters. Ryan could work as hotel greeter in the evenings for fifty dollars a week. The wrestling promoter prevailed on a friend. Ross Fawcett, owner of Fawcett Motors in Weston, to make Ryan a car salesman. Members of the Toronto Kiwanis Club promised Ryan would have financial aid if ever he needed it.

Gay days for a pious killer

Ryan’s future was smoothly paved when he was told by Warden Allen that he was to be released. If he had not reformed so grandly, and if such a strenuous campaign had not been launched, Ryan would probably have spent another twenty years in Kingston. Now he was free after merely eleven and one half years. Rarely, if ever, has a life sentence been so shortened.

Through Father Kingsley a Toronto Star reporter arranged to have Ryan leave the train, taking him from Kingston to Toronto, at Belleville. The Star worldcopyrighted a full story of the release and also hired Ryan briefly. For five days the Ryan by-line appeared in the Star. The theme of these effusions was “I was the true author of my own troubles.”

These were gay days for Ryan—parties, introductions and a long list of job offers. On a visit to the Shrine of the Little Flower in Toronto with Archbishop O’Brien of Kingston he was followed by Star reporters. The story was headed “Dazed by liberty. Red Ryan prays in little church.”

Ryan settled down to live with his younger brother, work at his two jobs and relax respectably. He watched wrestling matches from Jack Corcoran’s box at Maple Leaf Gardens with such guests as Magistrate Robert Browne. Among his several patrons was Senator O'Connor, then owner of the Laura Secord candy shops. For good appearances he picked up ten suits and a convertible, although he had left Kingston with a hundred and seventy-five dollars, most of it piled up from his niekel-aday wages for prison work.

Some Toronto policemen were not prone to welcome him home, others were impressed. One evening Ryan dropped into the police press room to chat with reporter Gwyn Thomas. A two-alarm

“If I went back to crime,” Ryan said, “it would ne parole’s biggest blow”

lire broke out and Ryan went along.

"When we got there I ran into a tough police sergeant who wouldn’t let me through the fire lines,” Thomas recalls. “He kept shouting ‘Get back!’ Then he saw Ryan and forgot about me. He clapped him on the back and introduced him to the other cops and the firemen. I thought they were going to forget about the fire.”

Ryan enjoyed it all. lie regularly drove to Kingston to see Father Kingsley and once dropped in on Warden Allen. In Toronto he gave a smitten secretary an assortment of gifts, the inevitable fur coat included, for Christmas. Among his male companions Ryan included i.t.-Col. Wallace Bunton, of the Salvation Army, with whom he lunched occasionally. One of the few reverses during the halcyon ten months occurred when Ryan asked Jack Corcoran to place a large banner outside the Ncalon Hotel announcing: Red Ryan Is Here! Corcoran, doing his best to have his protégé forget his past, would have nothing to do with it.

One night early in 1936 a burglar alarm rang in the home of Edward Stonehouse, a garage owner in Markham, Ont. Stonehouse and his son James jumped on the running boards of a new car being stolen by two men. Stonehouse was shot in the head and hurled from the accelerating car. His son was shot in the hands and abdomen. Stonehouse died of his wounds and his son died three years later partly as a result of the shooting. Ryan approached a Toronto detective investigating the murder and offered his services as an “undercover man.” He was turned down.

Then, on May 24, 1936, two masked men dressed in overalls, work shirts and railwaymen’s caps entered a crowded government liquor store in Sarnia just before closing time. The taller bandit held a .38-calibre revolver in one hand and a .45 automatic in the other. He hurdled the counter while his companion covered the customers and employees. Just then Geoffrey Garvey, an oil-company employee, approached the store and sensed something wrong. He retreated unseen and phoned the police station a half block away. Constable John Lewis arrived within minutes and was shot down before he could use his gun. Witnesses said the taller robber fired pointblank at him.

In the battle that followed twenty-six shots were fired before the two men fell under the guns of officers who followed Lewis. The smaller robber, identified the next day as Harry Checkley, a petty thief, died a few minutes after arriving at the hospital. Constable Lewis, the father of two children, died soon after. An hour later, without regaining consciousness, the taller gunman died. His hair had been dyed a deep brown but he carried a driver’s license issued to Norman John Ryan.

Two days later five people gathered at an unmarked grave in Mount Hope Cemetery in Toronto: Ryan’s younger brother, Corcoran, John Tunney, C. A. Connors and the hearse driver. Archbishop James McGuigan had decreed the body be buried in unconsecrated ground. There was no priest. The funeral director said three Hail Mary prayers and an Our Father, sprinkled some dust, and the body of Red Ryan was committed to the earth.

The ninety dollars he had in a bank account did not pay for his funeral. Confederation Life, the issuers of an insur-

ance policy on his life, had written a prominent condition. There was to be no payment if Ryan died during the perpetration of an illegal act.

In Kingston, after he tore up his photographs of Ryan, Father Kingsley said, “Never was a convict given such a golden opportunity to rebuild the wreckage of his past.” It was reported that R. B. Bennett “felt the letdown very keenly.” Col. Mullins said, “I thought I could tell when a man was telling the truth but Ryan fooled me.” There were angry newspaper editorials against parole and estimates of the effect Ryan’s betrayal would have on the parole system.

But his story was anything but over. There was immediate newspaper speculation that Ryan had been involved in much more than hotel greeting and car selling. Might he not have taken part in the Markham murder which he so audaciously offered to help solve? The answer came thirteen days after Ryan’s death when Dr. FT R. Frankish, a medico-legal expert, presented a report to Arthur Roebuck, then Ontario’s attorney-general.

“With regard to the Stonehouse case,” the report read, “1 am able to identify the revolver ... in the hands of Red Ryan at the time of Sarnia affair as the gun which fired the bullets into the body of young Stonehouse. We have also in your laboratory a toe rubber which was found in the Stonehouse car after it was abandoned by the robbers following the shooting. This rubber is a size nine and a half, practically new, and on the inner surface of the rubber . . . the indentation of a Goodyear Wingfoot rubber heel is plainly impressed. A pair of shoes was found in Ryan's home which iit perfectly the toe rubber. These shoes are heeled with Goodyear Wingfoot rubber heels.”

Frankish then gave a detailed description of how the peculiarly worn heel and the imprint in the rubber matched precisely. He said there was no doubt in his mind that Ryan was one of the two men involved in the Stonehouse slaying.

There was more. A month before Ryan was shot in May, a Bank of Nova Scotia

branch in Lachute, Que., had been held up by four men who escaped with $3,567. In August, Thomas Finnessey was arrested in Ottawa and confessed that among his companions in the robbery was Ryan and Edward McMullen, the safecracker wounded in the 1923 Ryan escape from Kingston.

There was a third Ontario crime in which Ryan definitely took part, an attempt to break open a safe at Ailsa Craig, Ontario, on December 5, 1935. During his freedom other Ontario crimes were committed which remained unsolved, including a bank robbery and a dozen safe-breakings. In the stolen car used for the Sarnia liquor-store attempt there was an assortment of safecracking equipment. In a garage rented by Ryan in Toronto was found nitroglycerine, dynamite, fuses and explosive caps.

Two things remain to be told of the Ryan story—the catastrophes that followed his death and the probable reason for his endless crimes and his morality masquerade.

One victim of Ryan’s faithlessness was Lather Kingsley. “He couldn't get his mind off the whole thing and he wasted away to nothing,” remembers his nephew, John Kingsley. “He left the parish not long after the Sarnia affair and spent two years iñ a convalescent home, practically bed-ridden. He lost interest in everything until he died in 1941. Ryan might just as well have taken a gun and shot him.”

A wider disaster was Ryan's legacy to his fellow law-breakers and to Canada. On the night of his release he said one fact would keep him honest. “After all the publicity my case has received,” he said, “if I were ever to go back to a life of crime it would be the biggest blow that the ticket-of-leave system could receive.”

Perhaps Ryan wasn’t exaggerating. During 1935-36, the year in which Ryan was released, there were four hundred and thirty-one prisoners freed on ticket of leave from federal institutions. The previous year there had been five hundred and fifty-four. But fourteen years

after his release the Canadian average per year was about two hundred and seventy-five, while almost all other Western nations were making increased use of parole and proving its effectiveness.

It is, of course, erroneous to attribute solely to Ryan this state of affairs, but his case did play a significant part. J. Alex Edmison, a writer on penal reform and a member of the four-man Eauteux committee on remissions which reported to parliament on parole reform in July, 1956, feels that “no other single factor has influenced public opinion more against parole than the Ryan matter.” D. W. F. Coughlan, director of Ontario’s probation service, says, “The case of Norman Ryan put back the progress of parole in Canada by fifteen years. That one spectacular case did more against the system than the proven record of thousands of men has done for it.”

I here is finally the question of explaining Norman Ryan. Why did he never learn? Why did he return to violence when he was free, prospering in a good life? And as was so often asked, how could such a personable, intelligent and apparently sincere man mislead so many? In answer to these questions, a very reasonable assumption may be made.

Dr. B. T. McCihie, then deputy minister of health for Ontario, said after Ryan was killed, “I suppose he would fit into

the group we call psychopathic personalities.” This probability is also accepted by Dr. Julian Blackburn, head of the department of psychology at Queen’s University.

Psychopaths, according to Abnormal Psychology and Modern Life, an authoritative textbook, do not exhibit symptoms usually associated with mental illness by most laymen. In general, such individuals show a marked lack of ethics and an inability to follow socially acceptable codes of behavior, perhaps as a result of brain damage or abnormal early environment. A number of passages in the textbook have a clearly familiar ring for anyone who knows the record of Norman John Ryan.

Psychopaths are “typically average or above average in intelligence, are usually persuasive conversationalists, spontaneous, genial and extremely likeable. Upon brief acquaintance they usually make an excellent impression. However, closer acquaintance reveals a deficiency in moral and ethical values.” The psychopath, “despite the pleading of his family, exhortations from the clergy and punishment by the law, seems quite unable to profit from his mistakes in a socially acceptable manner. He frequently shows superficial regret for his misdeeds and may even promise in a very convincing manner to reform ...” ★