10 Worst Sociopaths To Have Ever Lived

10-Worst-Sociopaths-in-History

Welcome to WatchMojo, and today we’re examining the most notorious people who exhibit signs of sociopathy, those being antisocial behavior, manipulation, and a lack of empathy.

Bernie Madoff

When it comes to financial manipulation, it’s hard to beat the story of Bernie Madoff. Madoff had it all on Wall Street; he ran a multibillion-dollar company and held sway over the Nasdaq stock exchange. But his own hubris eventually got the best of him. Madoff confessed to his sons Mark and Andrew that he had orchestrated the largest Ponzi scheme in history through his Investment Securities firm, swindling investors out of billions. Mark and Andrew then turned on their father and reported him to the FBI, who arrested Madoff on a charge of securities fraud. He eventually pled guilty to 11 felonies and was sentenced to 150 years in prison, where he died in April 2021.

Richard Scott Smith

Fans of Showtime’s “Love Fraud” may recognize the name Richard Scott Smith, as he was the primary subject of the four-part documentary. Smith was a serial con artist, running numerous online romance scams and ruining the lives of multiple women. These women appear in the documentary, sharing their harrowing stories of being duped and misled. Smith would use a fake identity and marry his victims, then use their financial information to obtain a line of credit. He would then flee, off to marry someone else, leaving his previous partners both heartbroken and in severe debt. Smith was known to have married at least ten times before he was arrested at the end of the series.

Anna Sorokin

Financial schemes are getting harder by the day, thanks to rapid technological advancements, but they still happen. Just ask Anna Sorokin, a Russian-born woman who defrauded various institutions of nearly $300,000. Having emigrated to New York in 2013, Sorokin quickly became a master manipulator. She invented a new identity - Anna Delvey - and forged financial documents to appear like a rich German heiress with access to a multimillion-euro trust fund. With these documents, Sorokin secured massive loans, which she used to sustain a lavish lifestyle. However, her deceit was exposed when she duped her friend Rachel DeLoache Williams of over $60,000. Williams alerted the police, leading to Sorokin’s arrest in a sting operation. She subsequently served two years in prison.

Billy McFarland

Called “the poster boy for millennial scamming” by Vanity Fair, Billy McFarland is widely known as the man behind the ill-fated Fyre Festival. Well, ill-fated isn’t the right word. More like manipulative. Taking place in the Bahamas, the Fyre Festival was marketed as a luxury music event with villas, gourmet food, the whole nine yards. Visitors paid good money to attend, but upon arrival, they were met with a horribly planned disaster that bore no resemblance to the promised opulence. Tons of lawsuits emerged accusing McFarland of fraud, and he was found guilty on two counts. He was ordered to pay $26 million in damages and served three and a half years in prison.

Joe Exotic

The Tiger King himself operated the Greater Wynnewood Exotic Animal Park in Oklahoma, known for its prominent display of large cats. And, as chronicled in the famous Netflix documentary, he had a fierce rivalry with Carole Baskin, the owner of Florida’s Big Cat Rescue. Exotic displayed numerous sociopathic tendencies, which were on full display in the documentary. Despite his purported love for animals, he was continuously alleged to have mistreated those in his park. Not only did he publicly accuse Baskin of killing her missing husband, Don Lewis, he also put out a hit on her which failed and led to his arrest. Exotic was convicted on charges of animal mistreatment and attempted murder-for-hire, and sentenced to 21 years in prison.

Dorothea Puente

Known as the Death House Landlady, Dorothea Puente sounds like someone out of a fairy tale. She opened a boarding house in Sacramento and seemed like an upstanding member of the community, donating to various charities and using her boarding house to host AA meetings. She also aided her elderly guests in setting up their Social Security checks. However, this was all part of Puente’s grand plan. Throughout the 1980s, the matron killed nine guests of her boarding house, buried their remains in her yard, and cashed their Social Security checks. It shows that Puente was a maniac who was highly aggressive and driven primarily by her own financial gain.

Elizabeth Holmes

And speaking of people willing to deceive for financial gain, let’s talk about the infamous Elizabeth Holmes. Like Bernie Madoff, Holmes manipulated investors with her company Theranos, which claimed to have revolutionized blood testing with a fancy new machine. However, this machine never actually worked. Holmes not only lied to investors about the company’s capabilities, but she lied to her own customers through the machine’s bogus results. Theranos raised more than $700 million, and Forbes valued Holmes as the youngest self-made female billionaire in American history. But it all came crashing down when investigators looked into the company and uncovered a massive web of deceit. Holmes was charged with fraud and sentenced to 11 years in prison.

Diane Downs

Called a “deviant sociopath” by one psychiatrist, Diane Downs gained notoriety for a particularly heinous crime conducted in 1983. On May 19, Downs shot her three children, then wounded herself in the left arm. She subsequently rushed them to a hospital, claiming that they had been the victims of an attempted carjacking. However, hospital staff were immediately suspicious of her story. Two of the children survived, but one tragically passed from her injuries. Following an official investigation, Downs was arrested nine months later and convicted largely on the testimony of one of her surviving children. She supposedly committed the acts because the man she was entangled with didn’t want kids in their lives. In 1984, Downs was sentenced to life in prison.

Ted Bundy

Ask any professional and they’ll tell you that Ted Bundy was as mean as they come. His own attorney, Polly Nelson, called him “the very definition of heartless evil.” Biographer Ann Rule said he was “a sadistic sociopath.” Even Bundy labeled himself as “the most cold-hearted son of a [gun] you'll ever meet.” “Gun” is our own word. Bundy was an attractive man, who skillfully manipulated his persona to enchant women, often luring them into his car, where he would restrain and kill them. Even after his arrest, Bundy tried to maintain his innocence, weaving lies for lawyers, the media, and visitors alike. However, as the truth closed in, he eventually realized that the game was up and confessed to killing 30 people.

Charles Manson

At his twelfth parole hearing, Charles Manson was said to have a “history of controlling behavior.” That’s putting it lightly. Perhaps the most infamous cult leader of all time, Manson was the head of his eponymous Family, which gained notoriety in 1969 after killing actress Sharon Tate. But Tate was just one of nine victims, most of whom Manson murdered by proxy, through his manipulated Family members. His motive is still ambiguous, but author Vincent Bugliosi believes that he intended to start a race war. At the aforementioned parole hearing, the panel also indicated that Manson had no remorse for the crimes and harbored a total lack of empathy. He died in prison at the age of 83.

What do you make of these stories? Let us know in the comments below!