Often when we think of the world’s most famous criminals, we think of the disturbed child who grew up in an impoverished broken home and went on to become a ruthless and twisted serial killer. Ted Bundy, for example, famously grew up in a broken home in which he believed his grandparents were his biological parents, and his biological mother was his sister. A variety of complicated psychological and physiological factors that led him to become one of the world’s most sadistic sociopaths, murdering more than 30 people and terrorizing countless others – but his troubled background is often knowingly referred back to in tales of his crimes.
We don’t typically imagine that the overachieving middle child of a wealthy, well-to-do family will someday grow up to be Public Enemy Number 1. Yet, some of the most dangerous criminals of the 20th century actually came from perfectly ordinary, even affluent families. These criminals risked their comfortable lives of luxury and their model families’ reputations for life on the run – and they all ended up behind bars in the end. These days, perhaps these wealthy criminals would be diagnosed with the pseudo-psychological disorder that’s lately been attached to privileged misbehaving youth, ‘affluenza’. Or maybe they were just nasty sorts: These are five notorious criminals who were born into money.
5. Charles Ponzi
Carlo Pietro Giovanni Guglielmo Tebaldo Ponzi – better known as Charles Ponzi – was born into a well-to-do Italian family in the city of Parma. After spending four years at University, he spent his life savings on a trip to America.
You can likely put the pieces of the story together from here. With only $2.50 in his pocket, Ponzi knew he had to find a way to make an honest living. Instead, he chose a faster – more criminal – route to earning a fortune first by committing small frauds and forgeries in American banks and later by originating one of the first large-scale investment scams in history.
After World War I, the U.S. post office began offering international reply coupons, which were intended to allow someone to mail a letter to someone in a different country and pay for that person’s postage when they replied. Charles Ponzi found a weakness in the system in which he mailed these coupons to countries with much higher inflation levels, and his partners would exchange that postage to receive a much higher value in U.S. dollars. This process was totally legal. However, once profits actually started rolling in, he began paying off early “investors” using money from more recent investors, essentially snowballing his profits. This process was entirely illegal, and gave rise to a new form of swindling wealthy investors known as a “Ponzi scheme.”
4. John Dillinger
Perhaps one of the most ruthless and notorious gangsters of the 1930s – and of all time – John Herbert Dillinger was originally the son of a hardworking grocer. Growing up in a middle-class family in Indianapolis, Indiana, he became somewhat of a problem child after his mother’s death and frequently acted out. As a teenager, he dropped out of school to work in Indianapolis machine shops but soon grew bored of that and would spend all night out in the city looking for easy money.
You know how his story turns out. After starting small robbing grocery stores and easily getting apprehended by local police, Dillinger graduated to robbing banks as soon as he got out of prison. Although he was apprehended, his incarceration was not uneventful. Just days after his arrest, eight of his partners escaped from prison in a violent shootout and returned to free their boss not long after. After that, Dillinger and his gang led the FBI on a cat and mouse chase in an unprecedented crime spree, robbing banks and terrorizing police all over the country. His life ended in a famous shootout at the Biograph Theater as the result of an FBI/police sting.
3. Bernie Madoff
The man behind the largest financial fraud in U.S. history was the son of a stockbroker in Queens, New York. Growing up fairly well-off, he eventually also married into money. His first business, Bernard L. Madoff Investment Securities LLC was established in large part thanks to a generous loan given him by his father-in-law, to the tune of about $50,000.
Once established, Madoff’s businesses and self-worth skyrocketed. He quickly became a prominent fixture on Wall Street and eventually became the non-executive chairman of the NASDAQ stock market. However, in 2008 all of his success came crashing down when it was uncovered that his multi-billion dollar investment business was nothing but a massive Ponzi scheme. In all, Madoff cost his “investors” upwards of $65 billion and is currently serving a 150-year sentence behind bars.
2. Herman Mudgett
Herman Mudgett, better known by his alias H.H. Holmes, was America’s first known serial killer. Born into wealth, Mudgett excelled in academics from an early age and developed a propensity for capturing small animals to perform “surgeries” on them at home. He attended medical school as a young adult but was quickly expelled for stealing corpses, which he would allegedly use for experiments as well as insurance fraud schemes.
Later, “Dr. H.H. Holmes” became a pharmacist in Chicago, where he developed a bad habit of seducing women, getting engaged and then murdering his brides-to-be. In addition to collecting on his victims’ life savings, he often donated their bodies to medical research.
The house he built for himself became known as “Murder Castle” and featured secret hidden corridors, soundproofing equipment, trap doors, gas jets designed to asphyxiate victims, a cremation kiln and other murder/torture devices. In later life, Mudgett became involved in a large-scale insurance fraud scheme but eventually ended up murdering his partner and 3 of his children for fear that they would give him up to authorities. These murders ended up doing him in, and he was sentenced to life in prison. The total number of bodies Mudgett/Holmes was responsible for killing is more than 200, by some accounts.
1. Machine Gun Kelly
George Kelly’s childhood was far from the rough and violence-ridden background you might expect of one of the most notorious gangsters and bootleggers from the Prohibition era. In fact, he was born into a wealthy family in Memphis, Tennessee, where he received a healthy, traditional Southern upbringing.
However, Kelly wasn’t a normal, traditional Southern gentleman. While he was fairly well-behaved growing up, he was a terrible student, receiving his highest grade (a meager C+) for “physical hygiene.” His academic shortcomings soon resulted in his acting out as a teenager, and he ended up spending the majority of his school career in detention or after-school services.
By the age of 19, he was married and had already fathered two children. In order to make ends meet, he picked up work as a cab driver – but it just didn’t cut it. It was at this point in his life when Kelly really gave up the “traditional” working life, partnering with a small-time gangster. After only a short time in the bootlegging business, he left his wife and fell in love with a new dangerous and woman named Kathryn Thorne. It was during his time with Kathryn that Kelly earned himself a small fortune, gained a notorious reputation as Public Enemy Number 1 and picked up a pretty sweet nickname, “Machine Gun Kelly” – a nod to his favorite bank-robbing accessory.