The St. Valentine’s Day Massacres

The St. Valentine's Day Massacres "Comic" Valentines

The St. Valentine’s Day Massacres “Comic” Valentines

The High Feast of St. Hallmark is upon us once more. If you are familiar with this blog, you will not be expecting anything laced, beribboned, or be-Cupid-ed, but rather a vinegar Valentine of holiday contretemps.

Compared with the incendiary flair of the normal Hallowe’en’s casualties, or the explosive potential of the 4th of July holiday, the roll of Valentine’s Day fatalities was relatively short.  In many of the accounts, the stakes seem to be very high, with one’s entire romantic future coming down to just one day: does he/she like me? Will he propose? Is he/she just trifling with my heart? Complicating things was the custom of sending anonymous “comic Valentines.” Also known as “vinegar Valentines,” comic Valentines were deliberately insulting cards, complete with grotesque pictures. The cards were designed to hit the recipients’ particularly sensitive points: baldness, a propensity for gossip, vanity, or stinginess. While these vulgarities were surprisingly popular—some historians suggest they were a social catharsis—they also seemed a flash point for sending people into a murderous rage. Hence this compendium of comic Valentine atrocities.  

There was some debate among the moralists as to whether comic Valentines were a form of defamation. Some said they were obscene and there are cases of postmasters either destroying or refusing to mail comic Valentines. This lady clearly was in the latter camp. 


How an Insulted Woman Cowhided Two Men Who Sent Her Obscene Literature.

A little cowhiding matinee occurred at the corner of Summer and Gest streets about six o’clock last evening and was witnessed by a crowd which seemed highly entertained by the performance. Mrs. Wendel Demmerling wielded a whip with terrible effect upon the faces, hands and backs of George Meyer and Henry Mishler, two employes of the Walsh Distillery.

Two or three days ago Mrs. Demmerling received two comic valentines on the blank side of which were written some vulgar and obscene reflections in German. The language was very insulting and charged Mrs. D. with being a bad and unfaithful wife. The documents asserted that she was “cranky” and a fit subject for the asylum.

The valentines were not objectionable, but the observations as to her character and mental condition roused the ire of the offended woman, and she determined to “lay for” the two men whom she supposed had written them.

Last evening, armed with a short thick whip of the blacksnake species, Mrs. Demmerling took her stand in front of her house, by which Mishler and Meyer passed on their way home from work. When they came along she raised her weapon and, with wonderful dexterity, laid it on the face and hands of Meyer. Mishler looked on and began to laugh at the performance. “Don’t you laugh. I’ve got it in for you too.” And Mishler’s face changed as the woman rained blow after blow upon him. The insulted wife did not desist until almost exhausted and both men wended their way home badly used up. Their faces were cut in several places, their hats mashed in, and the eyes of Mishler will be in mourning for several days. Mrs. Demmerling, when she had finished her well-executed job, remarked with a satisfied look: “I don’t think they’ll send any more dirty valentines to me.” She told an Enquirer reporter that she wasn’t done with Mishler, and intends to give him another dose at the first opportunity.

The victims of Mrs. Demmerling’s wrath are cousins of her husband, and have quarreled with the wife continually. Cincinnati [OH] Enquirer 21 February 1883: p. 4 


Get Louis E. Rayot, a Farmer, Into Serious Trouble.

Louis E. Rayot, a young farmer of St. Bernard, is in a peck of trouble with Uncle Sam. According to an affidavit filed by Postoffice Inspector Fred. M. Betz, Rayot has been guilty of sending out valentines, on the back of which he drew obscene pictures and wrote lewd and lascivious matter. These valentines, so it is alleged, were sent to various farmers and women in the vicinity of St. Bernard. The matter on the back of the valentines was of the vilest imaginable nature. It is said that he sent out 18 pieces of such unmailable stuff. Rayot is 27 years of age, and was but recently married. He was arraigned before United States Commissioner Adler, who held him in the sum of $1,000 to appear for trial on January 31. He furnished bond. Cincinnati [OH] Enquirer 23 January 1898: p. 8 

Poison pen missives weren’t the only thing in the mail: 


Young Lady Received a Bottle of Poison By Mail.

York, Penn. February 19. Miss Lulu Cole, of this city, received on Valentine Day a phial of poison by mail, and since has had eight letters threatening her life. The valentine and letters have been turned over to the postal authorities, who are making an investigation. Miss Cole thinks the letters were sent by a young woman out of jealousy. Cincinnati [OH] Enquirer 20 February 1903: p. 1 


“Poisoners,” said a chemist, “make use of Valentine day to send boxes of poisoned cake or candy to their foes.

“This fact is a sad reflection upon human nature,” he resumed. “Yet here is a worse reflection;. Once, in a poisoning case in St. Louis I testified that there were several deadly poisons that left no trace of any sort behind in the body of the victim. Well, the lawyers asked me what these poisons were, and I refused to divulge their names. ‘Such knowledge is too dangerous for the public at large to possess,” I said.

“The judge upheld me, and I didn’t give the names of the poisons. But do you know that within the next month I received 800 letters from all parts of the world asking me, on all sorts of plausible pretexts, the poisons’ names? And still, to this day, I occasionally receive such letters, especially in the valentine season. I’ve received over a thousand in all. That is to say, I have direct knowledge of a thousand persons who would, if they dared, commit murder.” Washington [DC] Post 20 March 1910: p. 56 

(Any actual accounts of poisoned Valentine’s chocolates? Chriswoodyard8 AT

Miser "comic" Valentine

Miser “comic” Valentine

“Comic” Valentines also poisoned relationships: 

Fifty years ago the daughter of James Martin, a well-to-do farmer, purchased an expensive dress against his wishes, and she sent him a comic valentine representing a miser. He never spoke to her since. Last week he died and left $15,000 to each of his children but this daughter, for whom he left a sealed envelope, which, when opened had her old valentine inside. Semi-weekly Interior Journal [Stanford, KY] 5 April 1889: p. 10 

Men, women, and parents alike sent and took offense at vinegar Valentines. 

For sending an offensive valentine to a lady, another lady has had a cup of hot coffee projected at her, across a boarding house table. A police justice has held all the parties, who belong to the first society on Gay street, for court. Baltimore [MD] Bulletin 27 February 1875: p. 8 

A few days ago a daughter to Patrick Connor sent an offensive valentine to a daughter of Daniel Courtney, for which Mrs. Courtney gave the Connor girl a severe beating with a broom handle, and was fined, with costs, $9.25. Springfield [MA] Republican 15 February 1858: p. 4 

vinegar valentine

Some gentlemen seemed to be oblivious about the effect of their “joke” Valentines.

This young gentleman’s fate ought to be a warning to all who are addicted to the odious practice of performing practical jokes. Last St. Valentine’s Day, merely for fun, he sent a very offensive valentine to a young lady for whom he had a tender regard. He expected her to take the insult as a joke. On the contrary, he was astounded, a few days after, to receive from her an indignant letter, commanding him never to enter her presence again. He has apologized and explained, explained and apologized, but all will not do. The lady is as obdurate as flint, and he is in terrible distress. Perhaps this public recital of his grief and penitence may induce her to relent; but whether it does or not, we advise our correspondent to forswear practical jokes forever. New York Ledger 25 August 1860: p. 8 

From The Strong Museum of Play

From The Strong Museum of Play

A Valentine Tragedy.

“Alas, how easily things go wrong,

A sigh too deep and a kiss too long,

And life is never the same again.”

Such is undoubtedly the wail of a New York man who sent two valentines. The one, as he thought, was going to his real sweetheart, the nicest girl in the world. It was all lace and gold and pink with blushing roses and cupids. The other, a comic one, with a particularly malicious purpose, was mailed to a girl he didn’t like.

But this was a case of “how easily things go wrong.” With the depravity of inanimate objects, these two valentines managed to get themselves mixed. We all know that creatures, like letters, collar buttons, shirtwaists which open in the back, the kitchen stove, shoe laces and other vicious objects, can deliberately do more to make life a failure than can all one’s enemies. The two valentines were hopelessly mixed. The lovely girl, with the angelic face and the tender heart received the comic effusion, an illustrated edition, informing her that she was “a vain and foolish creature.” The undesired girl—the one with a quaint and a colossal supply of vanity, received the dainty forget-me-not valentine with the initials of the sender in the corner.

The consequences are just such as might be expected in real life—the beloved one is inevitably offended and no blandishments or explanations will placate her injured feelings; while the tiresome other girl is going about among all her friends, including the angered sweetheart, showing the resplendent valentine, with its affectionate sentiments and its unmistakable initials.

And the moral? There is no moral.The Scranton [PA] Republican 17 February 1907: p. 4 

vinegar valentine 2

This Valentine-sender certainly had no notion he would ever be found out, let alone reprimanded by the lady: 


How Mrs. Johnson Punished a Clerk for Sending Her an Offensive Valentine

Chicago, Ill., Feb. 18, 1885. Mrs. B.F. Johnson, a married lady who is employed at the Brevoort House restaurant as cashier, has created quite a sensation by rawhiding John A. Lay, night clerk at the Continental Hotel. The lady ascended the stairway leading to the office while he husband awaited her on the sidewalk. She marched with a quick determined step to where Lay was at his post of duty. At the sight of her he turned pale, but in response to her request to speak with her down stairs accompanied her to the first floor. Arrived there the lady turned suddenly on Lay and said:

“What was your reason for sending me such a valentine as I received from you through the mail?”

“What valentine? Why—why—I sent you no valentine,” said the surprised Lay.

“Don’t you tell me you didn’t send it, for I know better. I know the exact place you mailed it.”

“It wasn’t me. It was Benedict that sent it,” gasped the young man, who seemed somewhat surprised at the accusation.

“Well, even if Benedict was the man who sent it , you knew of it and had a hand in it, and I’ll teach you how to improve your manners toward ladies.”


With the last remarked the speaker drew from underneath her cloak an ugly looking little rawhide, and before Lay could divine her purpose she began vigorously laying it across his shoulders. The blows fairly rained across Lay’s shoulders, and he danced around in agony and tried in vain to escape.

“You are nothing but a coward (whack, whack), and dare only attack women (whack), but I want you to understand (whack) that there is one woman (whack, whack, whack) that you can’t insult with impunity.”

She then quietly walked away and the whipped man returned to his post to nurse his wounds.

Mrs. Johnson, when asked about the affair, said she did not give Lay any more than he deserved. He produced an envelope which she said was the cause of the trouble. It was addressed “Miss Fisher, alias Johnson, Brevoort House Restaurant, city.”

“I think that any lady who valued her reputation would have resented such an insult,” said Mrs. Johnson, “just as I did. I have no alias, but my name is Mrs. Johnson. When I first began working here I was a widow and my name was Fisher, but I have since been lawfully married to B.F. Johnson.”


Mrs. Johnson said that Lay had been out of work for some time, and spent much of his time loafing around the Brevoort. She had no acquaintance with him, and never had spoken a dozen words to him. On Saturday morning, which was St. Valentine’s day, she received the opprobriously addressed envelope, which had to pass through the hands of several persons in the hotel before it reached her. It contained an alleged comic valentine, a cheap caricature, and also a sheet of paper, on which were written several insulting allusions to the lady’s husbands, her teeth and personal appearance, advising her to get a new wig and new clothes. She said she would not have cared for the contents of the envelope had it been properly addressed, but the address exposed her to unpleasant remarks, and it was intended as a deliberate insult. She knew a remedy at law would be no remedy at all, for Lay is financially worthless. So she took the matter into her own hands and meted out the deserved punishment to her traducer. She said that “Benedict,” to whom Lay charged the sending of the valentine, was the night clerk at the Brevoort House, through whom she learned that Lay was the party who sent it. New York Herald 19 February 1885: p. 10 

A horrifying enclosure with a comic Valentine led to a pair of deaths.



The shooting of Miss Meyer by Jacob Leuenburger, on Tuesday, is the absorbing topic at Sing Sing. The Coroner’s jury has rendered a verdict in accordance with the following facts: Jacob Leuenburger, a native of the Canton of Berne, Switzerland, about 15 years ago made his appearance in Sing Sing, and obtained work from Jacob Dirion. At the suggestion for Mr. Leuenburger, Mr. Dirion gave up his lager-beer establishment, and engaged in the manufacture of cider, and the distillation for various kinds of liquor. In a neat frame house, near the distillery, dwells the family of Mr. Dirion, with whom Mr. Leuenburer lived. In the same cottage also resided the victim, Miss Frederika Meyer, a niece of Mrs. Dirion, and about 20 years old. For some time past Mr. Leuenburger has shown great attention to Miss Meyer, but his love was not reciprocated, although her relatives appeared to favor his suit.

About 1 p.m. on Tuesday, Mr. Leuenburger entered the house and sat down to eat his dinner as usual. Mrs. Dirion and her sister, Caroline Smith, were sitting at the table, the former waiting upon him while Miss Meyer was sewing at a machine near the window, about eight feet distant. Mr. Leuenburger, after eating a little food, rose, walked toward Miss Meyer, hurriedly drew from his pocket a revolver without being observed and discharged a barrel at Miss Meyer, the ball entering her right temple. Her head fell forward and slightly sidewise upon the sewing machine, but she neither spoke nor moved, instant death having been caused. Almost at the same moment, Mr. Leuenburger discharged another barrel of his revolver at his own head, the ball entering near the center of the forehead. He fell to the floor, and let the pistol drop. It was immediately picked up by one of M. Dirion’s children and carried out of the room. During the confusion and alarm which followed Mr. Leuenburger rallied and tried to find his pistol. Failing to do so he seized a carving-knife, with which he stabbed himself several times. While he was thus engaged Capt. Mount, Chief of the Sing Sing Police force, made his appearance and took Leuenburger into custody. So great was the resistance offered by him that the aid of several citizens became necessary.

Up to this moment neither the Chief of Police, Dr. Woodcock, nor others who had the prisoner in charge, were aware that he had shot himself. As there was no fire at the police station, Leuenburger was taken to the Hoffman House, and the wound in his head probed, but the physicians failed to extract the ball, and thought it would be useless for them to do anything more, for they entertained no hope of his recovery, nor even that he would survive his injuries many hours. During the greater part of Tuesday night Leuenburer remained in a state of apparent unconsciousness, but at 8 o’clock yesterday, in the absence of medical advice, Mr. Rider, proprietor of the Hoffman House, ventured to give him a little stimulant. Shortly afterward he became quite conscious and somewhat communicative, calmly answering questions put to him.

It is stated that some one had sent him a caricature valentine on Tuesday morning, and inclosed a piece of twine and a nail, with the intimation that he might go and hang himself, for he could never secure the prize he sought, namely, the hand of Miss Meyer. Soon after receiving this, he proceeded to a saloon in the village where a young man named Lange, who is said to have won the affections of Miss Meyer, is employed. Leuerburger probably intended to shoot Lange, but, failing to find him, he left, repaired to his home, and there selected Miss Meyer as his victim. New York Tribune 16 February 1871: p. 8 

vinegar valentine 5

The anonymity of the comic Valentine seemed to madden some recipients.


Poor Joke Leads to Murder in West Virginia

C.R. Stewart Struck His Wife and Was Shot Dead by His Nineteen Year-Old Son

Charleston, W. Va., Feb. 14. C.B. Stewart, a grocer, died today from the effects of a shot fired by his son, Louis, aged 1 years, in a quarrel over a comic valentine.

The son who is in jail, says he was protecting his mother from an assault made against her by his father. Stewart received an offensive valentine, and accused his wife of having sent it. She denied the accusation and he struck at her, when the son fired the fatal shot.Grand Rapids [MI] Press 14 February 1900: p. 1 

In looking at Valentine tragedies, I ran across two lengthy non-fiction stories of young women who killed themselves ostensibly because of nasty Valentines. Obviously the Valentine may have been merely a “last straw,” in those suicides, but I wondered if the stories were exaggerated for literary effect. Apparently not.  

Suicide Caused by a Valentine. The coroner was called to hold an inquest at the house of J. Chesterman, 710 Broadway, on the body of a young girl named Margaret Cray, a servant in his family, who came to her death by taking laudanum. A companion with whom she slept testified that, when she went to bed, she left Margaret standing before the looking glass, decking her hair as if for a party, having previously performed her ablutions, and arrayed herself in her best gown. She also testified that the deceased spoke to her about taking some medicine, and playfully asked her if she would not like a little. When she fell asleep, the deceased was upon her knees at prayer. Perfect silence then rested upon the household, and in the morning Margaret Cray was dead, and an empty vial was on a stand beside her bed. She was a beautiful girl, but on the day before her death she had received a cruel valentine from one she had looked upon as a lover, which circumstance was probably the cause of her death. New York Express Daily National Intelligencer [Washington DC] 21 February 1847: p. 4

Another article says that she washed her entire person “as is done to dead bodies preparatory to the grave clothes being put on them.”  

And what whole worlds of domestic atrocities are suggested by this short article: 


St. Joseph, Mo., Feb. 15. In the probably fatal shooting here Sunday of William Smith, a carpenter, there came to light one of the strangest entanglements three persons ever lived under. A girl 22 years old, who shot Smith, avers to the police that she married him, knowing that her mother was already his legal wife. The three have lived for years together, the man as the husband of both. The shooting occurred over the sending of a comic valentine. The girl, who styles herself Mrs. Cora Smith, while her mother is known by the name of Mrs. William Smith, sent the carpenter a comic valentine. Smith grew angry when he received it and, after packing up his clothes, started to leave the house. [Which is when Cora shot him.] Salt Lake [UT] Telegram 15 February 1909: p. 4 

For more accounts of Vile Valentines, see this acerbic post from Undine of Strange Company.  And, if you would live to see another February 14th, take my tip: trash, unopened,  any anonymous mail that arrives in tomorrow’s post.  

Chris Woodyard is the author of The Victorian Book of the Dead, The Ghost Wore Black, The Headless Horror, The Face in the Window, and the 7-volume Haunted Ohio series. She is also the chronicler of the adventures of that amiable murderess Mrs Daffodil in A Spot of Bother: Four Macabre Tales. The books are available in paperback and for Kindle. Indexes and fact sheets for all of these books may be found by searching Join her on FB at Haunted Ohio by Chris Woodyard or The Victorian Book of the Dead.


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