LOVE GONE AWRY – The Case of Isaac Estrean

The complicated love story of Isaac Estrean and Annie Garlock came to a tragic end on March 9, 1914 on the streets of Toronto, Ontario in Canada. On that day, Isaac murdered his lover – 20-year-old Russian immigrant, Annie Garlock – and then turned the gun on himself. The Calgary Herald captured the story on its pages as follows.

(Note: All news articles are transcribed below for easier reading.)

“GIRL SHOT BY LOVER”

“Man Puts Bullet in His Lover Outside House”

“TORONTO, March 9. – About two o’clock this afternoon Annie Garlock, was shot dead outside the house at 406 Adalaide street west, by her lover, Isaac Estrene, who subsequently shot and fatally wounded himself through the stomach. The man now lies in the general hospital. They were lovers and the man was pressing her to marry him, but for some reason she delayed accepting his proposal.”

“They met outside her home this afternoon and without warning he pulled a pistol and shot her dead then made off along Adalaide street and turned the revolver on himself.”


The Calgary Herald got most of the story correct. However, Isaac’s attempt to take his own life was not successful. Two days after Annie’s murder, with Isaac still clinging to life, The Toronto World filled in some details of the case.

“IGNORANT THAT GIRL HAS DIED”

“Estrene Hopes to Die, and Offers to Wager He Will Not Stand Trial – New Evidence Found.”

“Isaac Estrene, the murderer of Annie Garlock, still lies in the General Hospital, but his condition is very critical. According to physicians he may die at any moment. Estrene is not yet aware that his victim is dead, although police officials informed him of this fact as soon as he was conscious. Yesterday, while conversing with a police official he repeatedly asked how Annie was. Estrene stated he did not wish to recover, as there was nothing now to live for; he believes his own death will occur within three days, and in one of his brighter moods yesterday offered to bet $10 that he will never stand trial.”

“Attempted Double Murder.”

“Beyond accounting for the whole of the six bullets discharged from the revolver, the only new point in the case unearthed by the police is that just after the murderer had put two bullets into his stomach, and just before he collapsed on the roadway, he attempted to shoot down the girl’s brother before he grappled with him. An eye-witness of the affair stated that Estrene pointed the gun and snapped the trigger at least twice on the empty cartridges. The brother then knocked the revolver from his hand.”


Isaac’s prediction that he would last no more than three days never came to be. Within a week, Isaac was recovering from his self-inflicted wounds. He would soon face trial for the murder of his lover, Anna Garlock. The headline of the March 19, 1914 edition of The Toronto World blared “ESTREAN WILL LIVE – HIS WAGER IS LOST”.

“ESTREAN WILL LIVE – HIS WAGER IS LOST”

“Isaac Estrean loses his bet. Last week, lying in the General Hospital on what he was confident was his deathbed, the Russian Jew, who shot and killed his sweetheart, Anna Garlock, and then turned his revolver upon himself, wagered Sergeant Umbach $10 that he would die of his self-inflicted wounds and not on the gallows. But he is almost better and will likely be discharged from the hospital in two weeks time.”

“On Monday morning Estrean’s name was called in police court and the case was remanded for one week. Two weeks from next Monday he may be able still to evade answering the fatal question, but three weeks hence there is no doubt he must say ‘guilty’ or ‘not guilty’ when the charge of murder is read out.”


The initial inquest into the case occurred by the end of March. Although Estrean himself did not appear at the hearing, his attending physician, Dr. Yellowlees, provided a full statement from Isaac to the court. Isaac’s statement, as well as testimony from witnesses appear in this remarkable news article from the March 31, 1914 edition of The Toronto World. On these pages, we learn the history of Anna and Isaac’s international love affair – complete with another woman and a meddling mother!

“MURDERED GIRL KNEW I WAS MARRIED – ESTREAN”

“In Statement Read at Inquest, Accused Russian Says Annie Garlock Paid His Passage to Canada, Tho Aware That He Had a Wife – Insanity Plea Probable.”

“’We find that Anna Garlock came to her death on March 9th at 406 West Adalaide street from the effects of bullet woulds caused by shots fired from a revolver in the hands of Isaac Estrean.’ The above was the verdict returned last night by Coroner Cotton’s jury in connection with the Adalaide street tragedy, in which Anna Garlock was killed by her lover, Isaac Estrean, who then attempted to take his own life.”

“The story of the crime, as told by the witnesses, was to the effect that the pair had been walking along the street when Estrean drew a revolver from his pocket and fired four shots at the girl and then turned the revolver upon himself. The antemortem statement of the prisoner, made the day after the murder, when he believed that he was going to die, was read by Dr. Yellowlees, who attended him. In substance it was as follows:”

“Estrean’s Statement.”

“Estrean had known Annie Garlock in Russia. He used to deliver goods from his store at her home, and had fallen desperately in love with her at first sight. They had been keeping company in the old country for some time when Annie came to Canada. A short time afterwards she wrote to him asking him to come to Canada, and later sent him the money to pay his passage. When he arrived here, he proposed marriage to the girl, but her parents objected for a reason which they would not give. After that Annie treated Isaac more of less as a joke, and tried to get rid of him. She met her cousin and started keeping company with him. This riled her lover.”

“On the day of the tragedy he wrote to his mother in Russia saying that he was going to take his life on that day at 3 o’clock. He then went to the grocery store to buy and orange, and while there accidentally met Annie. He left the store with her and the pair walked down the street. He asked her again to marry him, but she refused, and he then pulled the revolver and shot her. In his statement he did not mention anything concerning his supposed marriage in Russia.”

“Married in Russia.”

“Lea Levinski, 357 Palmeraton avenue, who visited the prisoner while he was in the hospital, was requested to tell what he had told her concerning his marriage at home. According to the witness’ interpretation of the man’s statement to her, Annie Garlock did not write to Estrean for some time after she arrived in Canada, and as he was deeply in love with her, he began to act so queerly that his mother feared for him, and begged him to get married to a girl in his own country. At first he would not hear of such a thing, but he was finally prevailed upon by his mother to do so. A short time before the date set for the wedding, he asked the girl to release him from his promise, offering to give her all the presents that would have been hers on the wedding day and to pay for her trousseau. He gave as his reason for not wanting to marry her, the fact that he did not love her, while he did love a girl in Canada.”

“The Girl Insisted.”

“The girl was not willing to release him, but told him to marry her, and if afterwards he was not satisfied they could go to the rabbi and get a divorce. He had lived with this woman for about three months after the marriage, when he received a letter from Anna asking him to come to Canada. This he did. The witness was unable to state whether he had first procured a divorce, or intended to get one. The main point brought out was, however, that he had written to Anna and told her that he was married, but she had still asked him to come to Canada.”

“Did Not Intend Murder.”

“T. C. Robinette, who appeared for the prisoner, questioned the witnesses regarding the mental condition of Estrean. From Lea Levinski he learned that he had asked some very queer questions of her. He did not appear to know that Annie was dead. In questioning Dr. Yellowlees, Mr. Robinette made the point that the main thing in the man’s mind on the day of the tragedy was the fact that he was going to commit suicide at three o’clock in the afternoon, and that the murder of Anna Garlock was merely incidental. The doctor also admitted that any man who commits suicide is temporarily insane. From Mr. Robinette’s line of questioning it would appear that he will enter a plea of insanity when the prisoner comes up for trial.”

“Dr. E. H. Frankish, who performed the post-mortem, stated that four bullets had entered the body of the girl, and that the death had been due to shock and hemorrhage.”

“It took the jury only a few minutes to arrive at their verdict.”


The jury at Isaac’s inquest made it clear that he would soon stand trial for the murder of Anna Garlock, but his health dictated otherwise. While no longer in the general hospital, Isaac was “far from being a healthy man.” The murder trial would not be held until sometime in October 1914. The news of the delay appeared in The Toronto World on April 16, 1914.

“ESTREAN MURDER CASE POSTPONED UNTIL FALL”

“Young Russian Jew Has Not Fully Recovered From Bullet Wounds”

“Isaac Estrean will not be tried for the murder of Anna Garlock until October 1914. At the criminal assizes yesterday T. C. Robinette, K. C., asked for this action because of prisoner’s physical condition. Estrean was but recently discharged from the hospital and is far from being a healthy man.”

“Miss Ray Levensky, one of a committee working to procure proper defence for Estrean, interpreted the indictment. Asked whether he pleaded guilty or not, the prisoner would not reply. Mr. Robinette then entered a plea of not guilty. Crown Counsel DuVernet agreed that the prisoner seemed to be not fully recovered from his self-inflicted wounds and did not oppose postponement.”



Ten months after the murder of Anna Garlock, justice was finally delivered to Isaac Estrean. The jury in his case delivered an immediate verdict. As reported on January 14, 1915 in The Toronto World, Isaac Estrean was going to Hamilton Asylum for the Insane.

“ESTREAN DECLARED INSANE BY JURORS”

“Russian, Who Shot Girl, Saved From Gallows by Medical Evidence.”

“Isaac Estrean, a Russian, was yesterday found ‘not guilty’ on account of insanity for the murder of Annie Garlock, by Mr. Justice Middleton’s jury at the assize court and was ordered to be detained at the Toronto jail pending the pleasure of the governor-general-in-council.”

“The prisoner, who was pale and timid, was unable to reply when asked to plead, but seemed quite unconcerned as to what was taking place. T. C. Robinette, who defended him, pleaded ‘not guilty’ owing to insanity.”

 E. A. DuVernet for the prosecution outlined the case, saying that Annie Garlock came from Russia some time ago and was followed about by Estrean, who was a married man. The girl, learning the customs of her new country, refused to keep company with the prisoner. On the night of March 9 the prisoner met the dead girl and when near 406 West Adalaide street he shot her four times, and then turned the revolver on himself.”

“’Now he is able to take his trial, he pleads that he was not responsible for his actions,’ said counsel.”

“Dora Sobel of 412 West Adelaide street stated that she saw the prisoner and Annie Garlock on the day of the murder. Prisoner spoke to Annie Garlock, who smiled. Estrean drew a revolver and fired three or four times at the girl, who ran towards her. The two girls went upstairs in the house. Annie Garlock collapsed into witness’ arms, knocking her down. The brother of Annie Garlock ran out to prisoner, who undid his coat and shot himself.”

“Sergt. Umback saw the prisoner in the hospital. He cautioned him. Prisoner confessed that he had shot the girl and himself. Estrean said that he was sure he was going to die and he wanted to bet witness $10 that he would die.”

“Dr. C. K. Clarke attended the prisoner in the hospital and saw him every day. On the day after the murder prisoner was in a rigid state of physical health. The man had many ideas of persecution and wanted to be taken out and shot. He did not seem to have any idea of what had occurred and did not know the girl was dead. Witness showed mental confusion and his brain was in conformity with the state of his health.”

“Dr. Smith, a brain specialist, saw prisoner on March 25. He was much reduced physically. His mental condition was that of apathy and dullness. When witness saw Estrean a few days after he was much improved and now he was a different man.”

“Mr. Justice Middleton said that murder could not be committed with impunity and the slayer plead insanity.”

“’There is one thing,’ he said; ‘the crown never made it a practice to try to get a verdict unless the evidence justified it. According to Dr. Clarke’s evidence, prisoner was not responsible for his actions.”

“The jury returned the verdict without leaving their seats.”


Isaac Estrean was sent to the Hamilton Asylum for the Insane in Hamilton, Ontario, as it was the provincial asylum prepared to house the criminally insane. He was most likely housed in East House (now Century Manor) – one of three buildings that housed patients on the Asylum grounds. From 1890 until 1920, East House was used for the purpose of holding the criminally insane. Beyond that, without accessing Isaac’s patient records, there is no way of knowing about his stay at Hamilton.

It was more than four years before the world heard the name “Isaac Estrean” again. On August 9, 1919, “SLAYER ESCAPES HAMILTON ASYLUM” was splashed across the pages of The Windsor Star. Isaac had escaped the Asylum.

“SLAYER ESCAPES HAMILTON ASYLUM”

“Hamilton, Aug. 9. – Isaac Eastern (sic) of Toronto, an insane criminal, escaped from the Hamilton asylum, wrenching off a couple of iron bars from a window and making his escape. It is said Eastern, a Russian, killed another in Toronto some years ago. He has been confined here since 1915. Dr. English, superindentent, does not regard the man as dangerous. Less than a month ago, Chartrand, another insane murderer escaped and has not been recaptured.”


Two days after his escape, on August 11, 1919, The Toronto World reported on the speculation that Isaac had the help of friends in order to gain his freedom. They do not, however, report that Isaac Estrean had been recaptured.

“DID FRIENDS AID IN ESCAPE FROM ASYLUM?”

“It is a prevailing idea among those in touch with the Isaac Estrean escape from the Hamilton asylum that the latter’s escape from custody was engineered by his friends to secure his permanent address.”

“Estrean, his friends say, is sane now no matter what his condition may have been when he shot his sweetheart, Annie Garlock, on Adelaide street in 1915. It is also believed that Estrean will be surrendered to the authorities if his sanity after an examination by an outside alienist can be substantiated. Some months ago the friends of the escaped man consulted a well-known lawyer and asked him to set the necessary machinery in motion to have the man examined, but nothing could be done, and from all accounts the friends have brought him to Toronto, where alienists will examine him.”

“With the certificate of sanity it is believed that Estrean’s release would follow in short order.”


A final mention of Estrean’s escape appeared on August 19, 1919 in The Leader-Post from Regina, SK. The short blurb offered nothing new – Isaac had still not been recaptured. It did, however, offer a picture of the escapee – a rare occurrence and an exciting find.

“Isaac Estrean, who escaped from Hamilton Asylum, where he had been confined since 1915 for the shooting of his sweetheart, Annie Garlock. He is now said to be going to Toronto to have his sanity tested and fight for freedom.”


I have been unable to solve the mystery of what happened to Isaac Estrean after his escape from the Hamilton Asylum for the Insane. After mid-August 1919, the story disappeared from the pages of the newspapers – at least from the papers that I’ve been able to access. It’s unlikely that he was recaptured and returned to Hamilton, as he does not appear in the Census of the Asylum in 1921. Was he ever examined by an alienist in Toronto? Did he somehow legally gain his freedom? Perhaps he returned to his mother and wife in Russia? How could he just disappear into the ether? 

We may never know how Isaac’s story ended. But the news accounts of Isaac Estrean’s ordeal paint an intriguing tale of love gone awry, murder, insanity, an asylum escape and a mysterious disappearance. I hope you enjoyed following along.


If you are interested in the history of the Hamilton Asylum for the Insane, be sure to check out my other posts on the topic by navigating to the “Categories” section on this site.

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