5 Terrible Things That Happened on Valentine’s Day

Several Valentine’s Days have been marked by tragedy.
Several Valentine’s Days have been marked by tragedy. / Carmen Martínez Torrón/Moment/Getty Images

For most people, February 14—Valentine’s Day—is a day that is synonymous with love, affection, and friendship. But throughout history, there have been Valentine’s Days where things didn’t go well. They went horribly wrong, in fact. Here are some terrible things that happened on the day of love. 

1. The Martyr of Saint Valentine 

Saint Valentine, 19th century.
Saint Valentine as depicted in the 19th century. / Heritage Images/GettyImages

Fans of all things romance owe a debt of gratitude to the man we now know as Saint Valentine—though his exact identity remains a mystery.

According to one version of Saint Valentine’s history, he was an ordinary priest who lived in the third century CE. He was going about his usual priestly duties during a time when Rome was ruled by the Emperor Claudius II, a.k.a. Claudius the Cruel. Claudius had been under the impression that lagging enlistment into his Roman army was because of the men’s strong attachment to their wives and lovers. To him, the solution was simple: ban all marriages and engagements to ensure that more men joined the Roman military ranks. 

Valentine realized the injustice and cruelty of such a decree and continued to perform marriage ceremonies in secret. When Emperor Claudius discovered the priest’s clandestine activities, he sentenced him to be clubbed to death and then, as if that wasn’t enough, to have his head cut off. Valentine died on February 14, around the year 270 CE.

For his great service in the name of love, Valentine was named a saint. You can see his skull on display at the Basilica of Santa Maria in Cosmedin, Rome. 

2. The Death of Theodore Roosevelt’s Wife and Mother

Theodore Roosevelt
Theodore Roosevelt. / Hulton Archive/GettyImages

For Theodore Roosevelt, Valentine’s Day 1884 was a terrible time. It was the day two of the most beloved women in the future president’s life died only hours apart. 

Roosevelt began that day as usual, working his job at the New York State Legislature until he was unexpectedly summoned home. He arrived to find out that his mother, Mittie, had died suddenly of typhoid fever. Later that same day, Roosevelt’s wife of four years, Alice Lee, succumbed to Bright disease, an inflammatory kidney disease. She had given birth to the couple’s daughter Alice only two days earlier. Roosevelt’s diary entry for that day was marked with an X and an inscription that said, “The light has gone out of my life.”

The tragic events of that day devastated Roosevelt. After finishing his term in the New York State Legislature, he left New York for the Dakota territories, where he embraced ranch life and took on the role of local sheriff for two years. Roosevelt then returned to the East Coast, became governor of New York, and in 1900, became William McKinley’s vice-presidential running mate. When McKinley was assassinated in 1901, Roosevelt began an eight-year stint in the White House as the 26th president of the United States. 

Roosevelt eventually found love with Edith Kermit Carow, whom he married in December of 1886. 

3. The Murder of Al Capone’s Rivals

Al Capone
Al Capone. / brandstaetter images/GettyImages

There wasn’t much love on the streets of the North Side of Chicago on Valentine’s Day of 1929. Unfortunately for some of gangster Al Capone’s rivals, someone had them murdered on that day. 

In 1920s Chicago, several gangs ruled the streets. The Prohibition Era was in full effect, making bootlegging a lucrative endeavor, along with other unsavory businesses like gambling and prostitution. There was a lot of money to be made—and every gangster wanted their piece. Capone, the head honcho in town, was raking in upwards of $60 million in his business ventures. His main rival was none other than George “Bugs” Moran, another of Chicago’s kingpins at the time. 

On February 14, 1929,  gunmen dressed as police officers entered the garage of one of Bugs Moran’s bootlegging operations and pretended to arrest the seven men there. The imposter police officers then lined them up and shot them while they stood facing a wall on the premises. Capone was never charged with the crime. However, all signs point to the notorious gangster, as all seven of the murdered men were associated with Bugs Moran. 

4. The Accidental 1945 Bombing of Prague

February 14, 1945, was a day of horror and sadness for the citizens of Prague. Allied forces bombed Prague, thinking it was the German city of Dresden—the actual target of the attack. The accidental aerial assault resulted in 701 deaths and 1184 injuries, all of them civilians. Hundreds of homes and historical sites were destroyed and 11,000 people were left homeless. 

Navigation errors were said to be the cause of the deadly miscalculation. The planes’ radars were not working properly, forcing the Eighth Army Air Force squadron to manually calculate the distance to their target of Dresden, situated 75 miles northwest of Prague. But their calculations were off. Due to that grave error, a squadron of 40 B-17 Flying Fortresses mistakenly dropped 152 tons of bombs on the innocent people of Prague. 

5. The Stardust Nightclub Fire

For people gathered at Stardust Nightclub in Dublin for a Valentine’s Day disco party, February 14, 1981, was a tragic day. Of the 841 patrons attending the party, 48 people died and 200 were injured.

At just after midnight on February 14, a fire began in the roof space above the club. With the music blaring among the jubilant festivities, no one noticed the fire until the heat melted the roofing materials and hot substances began dropping on the partygoers’ heads. A panic ensued. People rushed to the exits only to be hampered by several obstructions—padlocked emergency exits, sealed windows, and excessive amounts of tables and chairs. Emergency responders were dispatched to the scene of the fire, but tragically, many of the people inside had already succumbed to the smoke and flames. Dublin’s hospitals were flooded with injured and dying people

The fire was ruled to be caused by arson at the time. But in 2022, more than 40 years after the tragic inferno, families of the victims renewed their demand for a new inquest due to the lack of evidence pointing to arson as the cause of the fire.