Roaring: Bootleggers And Gangsters

On Crime In 1920s America

A young man in his mid-to-late 20s enters your establishment. He’s well groomed and dressed in a nice custom suit, and he knows about fine dining and good cigars. He prefers Templeton Rye, a whisky made in Iowa for the Prohibition era, and of course a gentleman like this enjoys the company of women. He speaks well, he’s charming and he seems like the kind of guy you’d love to have a drink with.

This young man is also the head of one of the most feared yet respected criminal organizations in American history. He is responsible for a major portion of the liquor being provided for speakeasies across the country. He is the one behind various bombings and assassinations that have killed hundreds. This gentleman who speaks so well, dresses well and knows about the finer things in life, is both refined and savage, both classy and shady, and both feared and beloved.

Al Capone was the face of the 1920s crime wave that Prohibition caused, the most infamous gangster in American history.


When Prohibition became law in 1920, the feeling was crime rates would dip and men would stay home to take care of their families. It was a strong motivating factor towards the public coming to embrace a solution that today many would balk at. Unfortunately, Prohibition’s reality was that it arguably was the biggest driving factor towards the 1920s crime wave.

With liquor and alcohol becoming near impossible to get, some men took matters into their own hands and tried to distill some homemade alcohol themselves. This was a risky and sometimes deadly decision, as police would raid homes and catch the illegal act taking place in bathtubs. Of course, the amateur attempts also could lead to toxic drinks being made, which would kill some.

These amateur attempts tended to be for those who were less wealthy or couldn’t afford a visit to the speakeasy. So, if you were poorer and had to resort to such cheap liquor, there was a chance you could die from the drinks themselves. It’s not much different than today where some drug dealers might offer amateurishly created drugs that have been fatal for those who buy them.

But for the more wealthy, the speakeasy was available and the speakeasies had much better distilled liquor. Why? Businessmen realized that if they smuggled liquor from countries such as Canada or the Caribbeans, they could offer the real thing to restaurants who would pay them to stock their menus. Speakeasies were also valued customers, and if you were a successful smuggler you could make it a lucrative business. These smugglers would become known as “Bootleggers” but another term for the practice was “Rum-Running”.

Of course, once word got out that rum-running was a risky yet rewarding business venture, others got involved and competition naturally took over. And instead of slashing prices, competition when dealing with something illegal involves more violent and malicious counters and less open sales offers — whether it was burning rivals’ vehicles so they could not travel across a border or stealing smuggled liquor while competitors were on route to a business transaction.

But that was small stuff compared to the lengths others would go to get ahead. These bootleggers would eventually join or lead organizations that specialized in making a business out of rum-running. And in turn, gangs would spring from them that would turn the age of Prohibition — the age that was suppose to lead to less crime and a more pious society — into an era of violence and blood money.


The gangs that would spring up in the big cities during Prohibition would all become part of an infamous time in American criminal history. Some of them would be the forebears of the Mafias that would come to give the FBI so much trouble in the later decades. They would be one of the major images that come up in one’s mind when the 1920s were mentioned.

There were many organizations but the ones that seem to stand out the most were the Five Families of New York, the Philadelphia Mafia and the Chicago Outfit.

The Five Families would go on to be the face of criminal organizations in later decades, but in the 1920s, they were just getting started. While they were putting in motion the foundations that would make them infamous, this was not the decade they ran things.

The Philadelphia Mafia was much more involved. They involved themselves with bootlegging and expanded operations into New York and Chicago. To this day, the Philadelphia Mafia is thought to be involved in criminal activity.

But the one that really dominated this decade was the The Chicago Outfit, run by the young man we were introduced to in the introduction of this chapter: Al Capone.


Capone was born to immigrant parents, a father who was a barber and a seamstress mother. He was the eldest of nine children, and he attended a strict Catholic school in which he excelled in grades but had such bad behavior he was expelled as a teenager for hitting a female teacher in the face. He would be mentored and looked over by Johnny Torrio, a major New York City gangster.

A Brooklyn native, Capone got involved with various small gangs and even worked for a bit with the infamous Five Points gang. He made other ends meet by working at a nightclub, where he was slashed in the face by the brother of a woman he inadvertently insulted. The scar left over would give him the nickname “Scarface,” a nickname he came to loathe. There are unconfirmed claims that the man who slashed his face would ironically be hired as Capone’s bodyguard later in life.

He married young, at age 19, to Mae Josephine Coughlin, a “shotgun wedding,” really, as she had become pregnant with what would be their only child before the wedding. She would give birth a month before marriage. Coughlin remained his wife for the rest of his life, even through the criminal cases, public scandals and the bevy of mistresses linked to him.

Capone headed for Chicago in his 20s, and there he would rise to the top. And it was there that Capone would make his name, as he would go to great lengths to be rid of bootlegging competition. This included attempted and successful assassinations of competitors and even bombing restaurants that refused to do business with him. It’s been estimated at the very least that 100-plus deaths from the bombings and assassinations could be linked to him.

The aggressive actions against competition and successful bootlegging (coupled with various money-making projects such as racketeering, gambling and brothels) allowed Capone a wealthy lifestyle, owning a mansion in Miami and becoming a known public figure who flaunted his wealth. When asked about his “alleged” criminal activity, he would simply say, “All I do is satisfy a public demand.”

Capone’s gang was powerful, paying for whole train cars to keep Capone safe, and having policemen and politicians in their payroll to keep themselves out of trouble. This, of course, made them feared, but Capone’s charitable contributions and good relationship with the poor made him a hero to some.

Capone’s luck began to run out towards the end of the decade. His reported planning of the St. Valentine’s Day Massacre — in which rival gangsters were executed in public on St. Valentine’s Day — led to scandal for politicians that he had paid off, and some lost their office. The FBI began to hunt him down as well, and he had to deal with various cases brought against him; he even had a near-one-year-stay in jail waiting for a court case to be decided. He escaped conviction every time. That would change later in life, but that’s for another decade.


Prohibition led to a demand in something that was illegal to supply. This allowed criminal activity among bootleggers and gangsters to flourish so that the public could get what they demanded. If you weren’t an amateur dangerously distilling alcohol in your home, you were likely enjoying a drink that had blood money behind it.

Crime rates have been estimated to have jump 20-plus percent in the first year alone, along with a more-than-300-percent increase in convictions when Prohibition finally ended in the early 1930s. Homicide rates rose by 78 percent, according to some estimates under the entirety of Prohibition.

The words of the Rev. Billy Sunday when Prohibition became law — “The reign of tears is over. The slums will soon be a memory. We will turn our prisons into factories and our jails into storehouses and corn cribs. Men will walk upright now, women will smile and children will laugh. Hell will be forever for rent” — were unfortunately not prophetic. Instead, it became a reign for bootleggers and gangsters who exposed the weaknesses of such an effort.