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St Valentine’s Day Eve is the lesser-known holiday that precedes the more widely celebrated, Hallmark Holiday of St. Valentine’s Day. As the name would suggest the holiday is celebrated the evening of February 13th.

Controversy of the holiday’s Origin
This holiday has been reported to have many historical origins all stemming from the 1920’s prohibition gangster era. The most widely accepted origin is that the holiday is celebrated in remembrance of the 1929 Saint Valentine's Day massacre, which resulted from a bloody turf war between two Chicago gangs, the South Side Italians led by Al Capone and Bugs Moran’s North Side Irish Gang.



However, some historians insist that the significance of St Valentine’s Day Eve to bootlegging culture preceded the massacre. Indeed, there are reports that bootleggers first gathered in an organized fashion on the 13th of February 1920, just as prohibition laws had taken effect. It is thought, that at this initial gathering, transportation and distribution strategies were discussed and that samples were given out to attract would-be customers. Some go as far as to call February 13th 1920 the birthday of modern bootlegging. Further reports claim that this 13th of February gathering transformed into a celebration that occurred annually at speakeasies throughout the 1920’s.



Some historians believe that Capone’s gang planned their bloody attack for the eve of the 13th, but were delayed by automobile mechanical issues and were not able to carry out the attack until the morning of the 14th.



Supposedly Capone’s gang planned their attack specifically on the “Bootlegger’s Holiday,” St. Valentine’s Day Eve, to send the message to all other Chicago crime syndicates that they were in control of all bootlegging operations in the city.

Celebration of the Holiday
Despite the controversial origins of the holiday, the celebration of St. Valentine’s Day Eve has long been observed since the 1920’s. During prohibition era, nearly every speakeasy in every city would be filled to capacity as hundreds of revelers would pack into tiny underground speakeasies to drink gin and whiskey. Bartenders would expertly prepare drinks for the joyous crowds and doormen would ensure that only patrons with the correct password would enter. Strict dress codes were enforced more than any other night. Often jazz music and piano playing would result in impromptu dance floors being filled by hoards of flapper girls. It was also not uncommon for illegal gambling and card games to take place in side rooms at these cavernous locations. It is thought that the fervor with which speakeasy patrons would celebrate the holiday reflected the desire to rebel against the social constraints of the conservative 1920’s era.

Historical effects of the St. Valentine’s Day Eve Holliday
Some historians have pointed to several events that occurred Feb 13th 1920 that seemed to have been influenced by the alcohol fueled observances of the St. Valentine’s Day Eve Holliday.

1. Upon catching wind of the first St. Valentine’s Day Eve gathering on Feb 13th 1920, US representatives to the League of Nations hastened the acceptance of Switzerland’s perpetual neutrality in order to close session in time to catch the tail-end of the celebration and enjoy some bathtub gin.

2. A group of colored gentlemen were stopped by the police on their way to an illegal St. Valentine’s Day Eve bootlegging gathering Feb 13th 1920. Upon being question by the police as to where they were going, the men scrambled to find a plausible cover story. They told the police that they were a professional basketball team on the way to practice and they said their team name was the Renaissance. Thus the first African American Pro Basketball team was inadvertently formed, ultimately resulting in the creation of the Negro National League.

3. The League of Women Voters formed in Chicago on Feb 14, 1920 on a day that it was known that the men would be so hung over from the celebration the night before and panicked about not having anything planned for St. Valentine's Day for their wives that they did not notice their wives leaving to form such a silly organization and thus did not attempt to stop it.

Celebration of St. Valentine’s Day Eve in the Modern Era
Despite the repeal of prohibition, the celebration of St. Valentine’s Day Eve continues strong in the modern day. Some would say the holiday has become even more secretive and exclusive than during the 1920’s. Celebrations are still held in secret locations, and entrances are still guarded by doormen. Often the St. Valentine’s Day Eve celebrations are held on location with another, more innocuous celebration such as a child’s birthday party. Typically a hidden door inside the house leads to the entrance of a back room or basement and ultimately into what many have called “the greatest time of their life!” As in the 1920’s, appropriate attire and the correct password are absolutely required.

Bootleggers and Rum Runners
From 1920 to 1933 the US government made the distribution of alcohol illegal. The term bootlegger originally referred to the manner in which illegal alcohol was transported in flasks concealed inside the legging of boots. While “Bootleggers” was the term typically given to criminals that transported illegal alcohol over land, those that transported it across bodies of water were typically referred to as Rum Runners. While the intent of outlawing alcohol was to reduce crime, it actually resulted in an increase, as criminal gangs began to develop sophisticated techniques to distill and transport illegal spirits. The ever-present demand for alcohol helped many of these gangs quickly gain power.





Speakeasies
The history of the rivalry between 1920’s Alcohol Prohibition Era Gangs in undisputed. Rival gangster outfits ran stores that sold “under-the-counter” alcohol as well as nightclub style establishments known as Speakeasies which served illegal alcohol in hidden, clandestine locations. It has been suggested that the name Speakeasies came from bar tenders’ requests that patrons “speak easy” or in a low tone of voice as to prevent discovery of the illegal establishment. Speakeasies ranged from dank, dismal places, such as basements, often referred to as “blind pigs,” to more luxurious establishments with high-class nightclub style acts.



A common feature to all types of Speakeasies was the requirement of a password from patrons to enter the establishment. This was intended to prevent discovery by law-enforcement. Often the entrance to a Speakeasy was located in the back of a store or even a residential home and typically consisted of a locked door manned from the inside by a doorman who would ask for the password through a slot in the door.



Origins of Passwords
Passwords were always required for people to gain access to a speakeasy and these passwords were typically not given to the general public. Passwords were typically passed by word-of-mouth or in hidden code in written invitations in order to ensure access by only select clientele and to prevent discovery by law enforcement. Passwords were often the phase “(a name) sent me.”

Speakeasy Culture & Style
Despite their often dirty and dismal locations, Speakeasies all attempted to maintain a high level of class. All patrons were required to dress formally. The formal attire of the 1920’s era soon became a hallmark of Speakeasy culture as men attempted to achieve the “look of success”.



Men’s Speakeasy Fashion
Men’s 1920’s speakeasy fashion had a wide-range of looks. All the newfound commerce of the 1920’s had resulted in the creation of mail-order catalogs from Sears Roebuck and Montgomery Ward. These exposed men everywhere to men’s urban fashion. With the birth of urban business wear the suit made a huge transformation during the Twenties. The suit came in three separate parts: the jacket, vest, and trousers.



Also, It was not uncommon for rich sportsmen to frequent a speakeasy after a day of playing golf or “hitting the links” as it was often referred:



Around 1924, the style of men’s suits shifted away from the thin-cut and pinched-waist look to what was known as the Jazz suit. The canonical speakeasy attire, the Zoot Suit, was inspired the by the typical fashion of gang members that supplied the illegal alcohol.



Women’s Speakeasy Fashion
Often less conservative than the men’s fashion, women’s speakeasy fashion was thought to reflect the rebellious nature of the women who would frequent these illegal establishments. Many surmise that speakeasy girls, or “flapper girls,” were rebelling against the conservative and sexually-restrained women’s fashion of the time.



The term flapper referred to a "new type" of young woman that wore short skirts and listened to jazz. They often flaunted their dislike of what was then considered acceptable behavior. Flappers drank, wore make-up, treated sex in a casual manner and otherwise flouted social norms.