Nelson Algren likened loving Chicago to “loving a woman with a broken nose.”

Valentine’s Day in Chicago has gone far beyond loving imperfect women. It’s oozed into the much less poetic territory of loving insane women, men with “the devil in them,” as Chicago’s matchless serial killer H.H. Holmes pegged himself, and loving (in that incomprehensible way of the doomed together) our world class gangland warriors, among them the ever-undisputed king of crime, Al Capone–without whom Chicago would be nothing more exciting than a particularly lovely and somewhat edgy example of what happens when people rally after a tragedy (see entry for the

Great Chicago Fire)


As a ghostlorist, I would say that Chicago defines itself–right under the tendency to say “To hell with what just happened”–in her passion regarding both love and hate, devotion and disdain.

Every February, while the rest of the world is buying flowers, chocolate and diamonds, Chicago is getting ready to mark the most infamous Valentine’s Day in history: the blustery day in February of 1929 when Chicago became the center of one of the most controversial eras in American history.

“Prohibition” brought fame to Chicago that would last, seemingly, to eternity. As in many other cities throughout the United States, Chicago remained very wet throughout the decade. Higher class operations were known as “speakeasies” while dram shops were called “blind pigs,” where customers would pay to see live animals and drink alcohol behind unmarked doors.

Most not familiar with Chicago history see Italian-American mob boss Al Capone as the unchallenged king of Chicago during this time; but in fact, throughout the decade, Al Capone went neck and neck each day with his rival, George “Bugs” Moran–head of the north side Irish mob in Chicago. The two of them fought for control of turf in the “Beer Wars,” much as the drug lords of Chicago and other urban centers fight today.

Their battles hatched some of the most lasting ghost stories in Chicago history, including stories about the hotels where Capone held court, fables about the sites of infamous shootouts, and the treacherous site of the St. Valentine’s Day Massacre, where seven of Moran’s men were lined up on that bitter morning and gunned down against the rear wall of a now-demolished garage. Even today, residents who live in the buildings adjoining this now vacant lot tell a curious tale: after a fresh snow in Chicago, you can sometimes see the outline of seven bodies in the snow, right where the rear north wall of the garage once stood.

In Chicago, coupled with these stories are the tales of some of the most ill-fated loves in American history. Consider the love story of Adolph and Luisa Luetgert, (the “Sausage King and Queen of Chicago”) which began as most immigrant love stories did on Chicago’s northside, but which ended with neighborhood children singing rhymes about Luisa being made into sausage by her husband.

Or the story of the Woman in Red, a beautiful young woman who attended the opening night party at the Drake Hotel with her fiance, New Years’ Eve 1920. Before the clock struck midnight, she discovered her love in the arms of another girl and hurled herself off the hotel roof. She is said to still be seen in wandering the halls, the skirts of her rosy gown swooshing around the corners, her sobbing still audible to startled guests.

Then there is the story of Herman Schuenemann, the captain of the “Christmas Tree Ship,” who sailed the

Rouse Simmons

to Michigan on his annual journey to bring Christmas trees back to Chicago–who was never seen again. It is said that the scent of pine needles can still be smelled at his wife’s gravesite in Chicago, nearly a hundred years later.

And there is eternal tale of “Resurrection Mary,” arguably Chicago’s most famous ghost, who died on a lonely Chicago road in the wee hours of the morning–only to haunt the city’s memory forever. As Chicago’s most long-standing dance partner, Mary has captured the imagination of generations hoping to help her find her way home at last.

This Valentine’s Day, whether you are a lover or a fighter, I hope you receive a kind word–and maybe even a fond embrace–from someone you love.

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