Looking back now, the St. Valentine’s Day Massacre seems like business as usual in Prohibition era Chicago but in 1929, a lot of people were really pissed that such a thing could happen. Sure, there had been a lot of murders in the city during the last decade, but not seven guys all at once, machine-gunned in cold blood in a garage.

The police believed they’d figured out how the massacre had occurred, but there was a lot of debate about who was involved – debate that continues today.

Police officers, crime experts, historians, gangster buffs, writers, know-it-alls, and the 900 guys who all tell you that their grandpa used to be a driver for Al Capone all have their favorite suspects when it comes to the St. Valentine’s Day Massacre. Some of them make sense, some of them don’t. Some of them are stupid, while others are just to sell a book or are just to get attention. Some suspects seem believable, but if you count them all, they add up to more than the number of actual killers.

So, take it all with a grain of salt but we’re going to take a look at some of the unusual – and sometimes unlikely – suspects in the St. Valentines Day Massacre.

On February 14, 1929, the most infamous gangland massacre in American history occurred in a dingy garage on the North Side of Chicago when five mobsters, plus a mechanic and a wanna-be gangster optometrist, were ripped apart in a hail of bullets. The events of that morning left a lasting effect on Windy City history and still reverberate today as several unsolved mysteries, strange legends, baffling tales and, of course, tales of ghosts.

Join us as we delve into PART ONE of the St. Valentine’s Day Massacre for the Halloween season – coming to you live from the American Hauntings Podcast Network!

In the summer of 1928, Al Capone was back in Chicago and was still building his empire. Things like gambling, prostitution, and, of course, liquor, were still making up the bulk of his profits – but he knew that wasn’t going to last forever. He knew that he needed to diversify, a lesson he learned from John Torrio, who knew that Prohibition would only last for so long. Capone’s most profitable alternative to liquor was racketeering. A racketeer was defined as the boss of a supposedly legitimate business operation. Labor unions were the most common operations. Using violence and intimidation, he organized the union or pushed a group of businessmen into a “protective association.” A worker or merchant who didn’t join or refused to stay in the union and pay tribute was bombed, beaten, or intimidated into changing his mind.

He was making a fortune that way -- but he had problems, too. Even as the millions continued to roll in, he found the problems hampering his business over and over again. The North Side Gang, now led by George Moran, was just as relentless as it had been under the leadership of O’Banion, Weiss, and Drucci. It was time to take care of that problem once and for all and on February 14, 1929 -- a deadly plan was hatched.