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Kitty Cat in Gangland

(October 1938–January 1939)

If The Corner was a street term for an intersection, the label “Gangland” for the larger area surrounding Jarvis and Dundas streets was a newspaper phenomenon. The name began in the wake of the vicious beating of a young policeman named Harold Genno on the night of May 8, 1938. That happened in an alley off St. Patrick Street, west of University Avenue, but, fueled by many further incidents, the designation “Gangland” soon moved eastwards to the environs of The Corner.[1] Nearby, there were a dozen small-to-medium-sized hotels within a few hundred yards of each other and, after 1934, when Ontario legalized the practice, they were all serving full-strength “beer by the glass” — a concentration that tended to draw those who were “looking for something” as well as others who, in one way or another, were out to make money out of what they were “looking for.” The term “Gangland” would be in the daily press for a season or two and, after that, lived on in the pages of Toronto’s old tabloid papers, Hush, Flash, Tab, Justice Weekly, and some others, till the last of their days in the 1970s.[2] In the beginnings of this, Mickey McDonald, and especially Kitty Cat, played significant roles.

In the early fall of 1938, increased violence among a half dozen small bootlegging operations in the Jarvis-Dundas-Church streets area was mostly directed against the best-organized and least-violent faction. This was headed by William “Lefty” Thomas, a street-corner newsdealer, who was also a bail bondsman, a bookmaker, and the money man behind bootlegging and beer-running operations run by agents of his in and around the Gangland area. At the same time, Thomas was a particular target of a violent street predator who was simply looking to “jack up” — extort — anyone, anyway he could. Bookmakers, bootleggers, and non-violent thieves were easy “marks” for Johnny “The Bug” Brown, a volatile ex-convict with a long record involving armed robbery, gun violence, and psychiatric assessment. Brown, who was born Ivan Stefanyk in Hamilton, Ontario, “hit up” Lefty and his crew several times before this became known outside Lefty’s circle of associates. Like Jimmy Windsor, as racketeers themselves, Thomas and his people could not be seen to give information against Brown, and they were not formidable enough to deal with him themselves. Inevitably, they guardedly talked to detectives. They wanted The Bug off their backs but feared to be part of any obvious effort to put him away.

While Mickey was “away at school,” Margaret “Kitty Cat” MacDonald (she was always “MacDonald”) got herself involved in all of this when she began co-habitating with Charlie Dorland, then Lefty Thomas’s fair-haired boy and principal lieutenant. In early October 1938, Charlie and Kitty moved into Apartment 2 at 539 Church Street. The place was elaborately furnished with money put up by Lefty, seemingly with the idea of combining two kinds of good time on the premises.

For ex-convict John Cullinan, who operated a bare-bones blind pig at 568 Church Street, the proximity of this new and better place would have been upsetting, even if, on the evening of October 4, 1938, Kitty and friend, Norma “The Blonde” Taylor, had not gone to Cullinan’s place to gloat. Soon Edward Near, a buddy of Dorland’s, took a telephone message at 539 Church. “If you don’t come and get Norma and Margaret, I’ll kill them,” Cullinan told Near. Together with Norm Cook, who did late-night beer deliveries for Dorland, Near did as asked.

In the wee hours of October 5, Charlie Dorland got a phone call that told him he had to go out. Then, soon after, Cullinan’s lady friend, Millie Dinwoodie, knocked at the back door of Apartment 2 at 539 Church. Kitty, who later said she “thought it was a friendly visit,” admitted Millie, who was followed in by Cullinan, Johnny “The Bug” Brown, Joseph Constantino, Verne Epter, and three other men. Most of the eight intruders were connected with one of three nearby bootlegging factions, or in the cases of Brown and his partner, Constantino, with the ongoing extortion and robbery of selected bootleggers and bookmakers. All but two of the eight had served time in prison or reformatory.

Cullinan began by ripping Kitty’s telephone off the wall, then announced there was “going to be a fight between Millie and Norma.” Brown pulled a gun to enforce matters. The fight wasn’t much of a contest. Millie, a big powerful girl, dragged The Blonde off a couch by the hair and throttled her. Then Cullinan and Epter both took a turn. Kitty and a woman named Rita McIntosh were also beaten up. The apartment’s new furniture and fixtures were completely wrecked at a cost of more than $200. Norma Taylor had her diamond ring and $18 stolen. A few days later, Margaret “Kitty Cat” MacDonald brazenly told the tale at a preliminary hearing in Toronto Police Court — which threatened to put all of her eight early-morning “visitors” in the penitentiary. As was reported, Kitty, wearing a stylish fur jacket, told Magistrate Robert J. Browne, “They smashed all the lights and threw the lamps on the floor. The place was in darkness. My clothes were ripped off my back.” What she described was termed “a miniature riot.”[3]

The incident itself was a front page story in the Globe and Mail of Thursday, October 6. The story played upon the same public fears as the Windsor Murder would three months later: violence, robbery, extortion, all of which happened inside a private residence, into which unwanted armed intruders forced entry. After this time, terms like “Gangland,” “Gangwar,” and “shakedown” appeared regularly in the Toronto press for months. The disquieted public was assured by Mayor Ralph Day and other members of the Toronto Police Commission that the situation would be cleaned up. Inspector Charles Scott of No. 2 Station at Dundas and Bay streets, said the same. “Gang warfare will not be tolerated by the police,” Inspector Scott promised. “An attempt will be made to prevent the different Jarvis and Dundas street gangs from taking the law into their own hands.”[4]

Mickey McDonald, after 20 months in Kingston Penitentiary, came home on November 7, 1938, and stepped into the middle of what for any of his kind would have been a trying situation. An acquaintance was living with his wife; Johnny Brown, one of his more violent jailhouse “friends,” had recently punched his wife in the face; and his wife, who liked living dangerously, was now trying to help the police put several of his “friends” — Brown in particular — away for significant lengths of time.

Late on the night of Saturday, November 12, Johnny the Bug and Joe Constantino went to Alexander MacDonald’s home on Poplar Plains Road with a bottle of liquor. Mickey went out to Brown’s car and shared the bottle with them. The three smoothed matters over between themselves. Kitty, already reclaimed from Dorland, was convinced by Mickey that her best course was to get on side with “Brownie,” Joe, and himself, who had just then made a plan to “take off” another of Lefty Thomas’s bootlegging establishments. Straight away, “The Cat” switched sides and drove the three in Brown’s car to the vicinity of 463A Church Street, where Mickey acted the part of the Trojan Horse. James Elder, the keeper of the house, would not have opened the door to Brown or Constantino. When the three barged in, others on the premises fled. Elder put up a fight and was blackjacked into submission. The raiders escaped with a small amount of cash, seven bottles of whisky, a bottle of gin, forty-eight quarts of beer, and a man’s overcoat. Thus, Mickey McDonald was out of prison all of six days before he committed the offence that would send him back again.

Mickey on the day of his arrest for the blackjack beating of James Elder, “Lefty” Thomas’s Church Street bootlegger. (Archives of Ontario, file 4-32 #409)

It was, of course, another Page One headline, since seemingly the law had lost its force in a central section of the city. The Globe’s story of Tuesday, November 15, 1938, was headed “Gang War Flare-Up Puts Two More In Jail.” Kitty’s participation in this violent event was the lead:

Blonde Margaret (Kitty) MacDonald, one of the central figures in the recent outbreak of warfare between rival bootlegging gangs in Toronto, was arrested with her husband last night on a charge of robbery with violence.

A man known to police as a member of a bootlegging gang was badly beaten by three men who broke into an apartment Sunday ...

Under arrest are Mrs. MacDonald and her husband, Mickey. The woman, known in the Church-Dundas-Jarvis district as Kitty, was the tenant of the apartment which was wrecked several weeks ago and furnished the spark which started the blaze of violence.[5]

Within a few hours of the robbery, the Toronto Police had rounded up Brown, Constantino, Mickey, and Kitty, but had to let all of them go when, at the last moment, James Elder quaked at preferring charges. After a Monday conference with Crown Attorney James W. McFadden, however, Detective-Sergeant John Hicks and Detective John Nimmo arrested all four again and charged them all with robbery with violence.

The trials of those connected to the major “Gangland incidents” of October 5 and November 13 did not get to court until January 1939. During the 51 days after November 20, 1938, including the night of James Windsor’s murder, Mickey McDonald was out of jail on $2,000 bail. During some of this time, he stayed with Kitty in a second-floor flat at 233 Broadview Avenue, where the couple did a lot of socializing with others of similar interests. It seemed convenient that Leo Gauthier, one of Mickey’s long-time partners-in-crime, was released from “the pen” on November 22. Leo was soon paired off with Marjorie Constable, a friend of Kitty’s who then “worked the street” in the vicinity of The Corner. A short time after their first meeting, Leo and Marje moved into an apartment at Sherbourne and Dundas streets. In the first forty-eight hours of 1939, the two couples rang in the New Year by bunking in together in a single room in the seedy Frontenac Arms Hotel at 306 Jarvis Street.

Three days after the Windsor Murder, on the morning of Tuesday, January 10, 1939, Mickey surrendered to face the music over the beating of James Elder. His trial, and the much-publicized trials of the others charged in connection with the same event, took place before County Court Judge James Parker and a jury that same afternoon. Elder and two others belonging to Lefty Thomas’s outfit had been charged as material witnesses and, so, as an alternative to going to jail themselves, were made to tell of what they saw, heard, and suffered at 463A Church Street in the early morning of November 13, 1938. For the defence, Brown and Mickey went into the box and told lying stories. Constantino and Kitty did not testify. The jury took four and a half hours to settle on guilty verdicts for Mickey, Brown, and Constantino. Kitty was found not guilty.[6]

“I am quite in accord with your verdict,” Judge Parker told the jury. “The evidence disclosed these men went to Elder’s place for a certain purpose and they carried out that purpose with violence.”[7]

The judge then remanded the three for sentence. Six detectives escorted the convicted men through the corridors of City Hall and, afterwards, to the Don Jail. The Globe and Mail of January 11 told its readers, “In gathering up the three, the police made their first arrests in the series of gang raids and shakedowns that have kept the Toronto underworld seething for several months past.”

A few days later, the eight invaders of Kitty’s apartment went before Judge Ian Macdonell and a County Court jury. They were all charged with robbery with violence, assault occasioning actual bodily harm on a female, burglary, and wilful damage to property. Their three-day trial ended in the conviction of Brown, Cullinan, Constantino, Verne Epter, and Millie Dinwoodie on one or more of the charges. Kitty, who switched sides again, seemed to glory in her role as star witness against the lot and, as ever, took obvious delight in showing herself off in beautiful clothes. The October 5 Gangland incident, her previous flamboyant appearance in Toronto Police Court, and this County Court trial were the first widely-reported “events” in Kitty’s establishing her almost 30-year reputation as Toronto’s most scandalous woman. In the 1930s, few women in Toronto would go into open court and boldly tell that they were living with a man other than their husband, to whom they had returned upon his release from prison, and no daily newspaper used the word “prostitute.” Instead, the press employed phrases like “The woman, known in the Church-Dundas-Jarvis district as Kitty...” which said the same thing in a code acceptable to the straight-laced citizens of Toronto the Good. Like the term “Gangland,” Mickey’s wife’s reputation, fueled by many future arrests and misadventures, would live almost as long as the scandal sheets. The connotations of the names “Kitty Cat” and “Gangland” would be virtually inseparable. In fact, one was a habitual frequenter of the other — and much of Toronto knew it.

January 27, 1939, was the day of final reckoning for all convicted of the two high-profile Gangland crimes. In Judge Parker’s court, Mickey’s father, in his thick Scottish brogue, made an “eloquent plea” for “my son, Donald, known as ‘Mickey’,” his errant boy of almost 32 years of age. Mr. MacDonald told a version of what had happened following Mickey’s return from prison:

...After a few days the telephone began to ring. His old companions found he was home. He tried to dodge them, and time after time we denied his presence in the house. Drink is his downfall. Whatever he did that night, it was not by deliberate choice. I do not ask anything for this boy other than the clemency of the court.[8]

Judge Parker sentenced “Michael McDonald,” John Brown, and Joseph Constantino to two years each in Kingston Penitentiary.

Then it was Judge Ian Macdonell’s turn on the Bench.

“Gang warfare, such as was never thought possible in Toronto, must end,” Judge Macdonell told the five who stood convicted before him. “I am afraid you must be made an example of. It is my painful duty to inflict severe sentences on you.”[9] Brown was then awarded five years consecutive to the two years he was given a few minutes before, and Constantino two years consecutive with his previous two. Cullinan, considered the ringleader on October 5, got five years. Verne Epter, once known as the undisputed head of the “Jarvis Street Gang,” was given four years. Millie Dinwoodie was let off with a suspended sentence. That day’s Toronto Star wore the banner: 5 OF GANG SENT TO ‘PEN,’ 7 YEARS FOR ONE.

The Star’s Page One lead-all story was titled “Pleading Father Hears Son Sent to Penitentiary.” Because of Alexander MacDonald’s pathetic appeal in court, the story concentrated largely on Mickey, who got only two of the 22 years handed down. Mug shots of the five who were “going inside” appeared together in the Star and the Telegram, on Page Two of both papers.

Johnny “The Bug” Brown, the man with the gun in the Toronto Gangwar of 1938. (Library and Archives Canada)

Mickey’s two-year sentence was by this time the least of his worries. Already he had reason to believe that he would be charged with the murder of James Albert Windsor. His days as a criminal of minor importance were over.