According to recorded history, back on February 14, on or about the year 278 A.D., Valentine, a holy priest in Rome in the days of Emperor Claudius II, was executed.
Under the rule of Claudius the Cruel, Rome was involved in many unpopular and bloody campaigns. The emperor had to maintain a strong army, but was having a difficult time getting soldiers to join his military leagues. Claudius believed that Roman men were unwilling to join the army because of their strong attachment to their wives and families.
To get rid of the problem, Claudius banned all marriages and engagements in Rome. Valentine, realizing the injustice of the decree, defied Claudius and continued to perform marriages for young lovers in secret.
When Valentine's actions were discovered, Claudius ordered that he be put to death. Valentine was arrested and dragged before the Prefect of Rome, who condemned him to be beaten to death with clubs and to have his head cut off. The sentence was carried out on February 14, on or about the year 270.
Legend also has it that while in jail, St. Valentine left a farewell note for the jailer's daughter, who had become his friend, and signed it "From Your Valentine."
For his great service, Valentine was named a saint after his death.
In truth, the exact origins and identity of St. Valentine are unclear. According to the Catholic Encyclopedia, "At least three different Saint Valentines, all of them martyrs, are mentioned in the early martyrologies under the date of 14 February." One was a priest in Rome, the second one was a bishop of Interamna (now Terni, Italy) and the third St. Valentine was a martyr in the Roman province of Africa.
Legends vary on how the martyr's name became connected with romance. The date of his death may have become mingled with the Feast of Lupercalia, a pagan festival of love. On these occasions, the names of young women were placed in a box, from which they were drawn by the men as chance directed. In 496 AD, Pope Gelasius decided to put an end to the Feast of Lupercalia, and he declared that February 14 be celebrated as St Valentine's Day.
Gradually, February 14 became a date for exchanging love messages, poems and simple gifts such as flowers.
1in 1929 - Four men dressed as police officers enter gangster Bugs Moran's headquarters on North Clark Street in Chicago, line seven of Moran's henchmen against a wall, and shoot them to death. The St. Valentine's Day Massacre, as it is now called, was the culmination of a gang war between arch rivals Al Capone and Bugs Moran.
George "Bugs" Moran was a career criminal who ran the North Side gang in Chicago during the bootlegging era of the 1920s. He fought bitterly with "Scarface" Al Capone for control of smuggling and trafficking operations in the Windy City. Throughout the 1920s, both survived several attempted murders. On one notorious occasion, Moran and his associates drove six cars past a hotel in Cicero, Illionis, where Capone and his associates were having lunch and showered the building with more than 1,000 bullets.
A $50,000 bounty on Capone's head was the final straw for the gangster. He ordered that Moran's gang be destroyed. On February 14, a delivery of bootleg whiskey was expected at Moran's headquarters. But Moran was late and happened to see police officers entering his establishment. Moran waited outside, thinking that his gunmen inside were being arrested in a raid. However, the disguised assassins were actually killing the seven men inside.
The murdered men included Moran's best killers, Frank and Pete Gusenberg. Reportedly Frank was still alive when real officers appeared on the scene. When asked who had shot him, the mortally wounded Gusenberg kept his code of silence, responding, "No one, nobody shot me."
The St. Valentine's Day Massacre actually proved to be the last confrontation for both Capone and Moran. Capone was jailed in 1931 and Moran lost so many important men that he could no longer control his territory. On the seventh anniversary of the massacre, Jack McGurn, one of the Valentine's Day hit men, was killed him in a crowded bowling alley with a burst of machine-gun fire.
McGurn's killer remains unidentified, but was likely Moran, though he was never charged with the murder. Moran was relegated to small-time robberies until he was sent to jail in 1946. He died in Leavenworth Federal Prison in 1957 of lung cancer.