Modern History’s Smartest Criminals


If the truth be told, the smartest criminal of all-time likely doesn’t appear on this list. That’s because the smartest criminals’ crimes go undetected. Or at best, the criminal is never identified as the perpetrator of a crime, which remains unsolved, baffling the police and other authorities. There have been many possessed of superior mental faculties who chose to pursue a life of crime, some for financial reasons, and some to torment the police, taunting them with their ability to strike and elude capture. Many serial killers, as this list demonstrates, had IQs considerably above average. Studies conducted by criminologists, psychologists, and psychiatrists continue to ask why. The answer is elusive, subject to speculation.

There are also those who used their gifts of superior intelligence to steal, through outright armed robbery and through elaborate schemes to burglarize well-protected museums, stores, and banks. Still others have relied on fraud, posing as those they were not to steal goods, services, and cash. All the criminals here, excepting only a pair of brothers who escaped on a legal technicality and a murderer who committed suicide, were caught and punished for their crimes. All revealed exceptional intelligence to their captors. Here are 10 of the smartest criminals of all-time, their crimes, and the prices they paid for living on the wrong side of the law.

10. Frank Abagnale

Frank Abagnale gained international celebrity through his own book and the film made by Stephen Spielberg based on it, Catch Me If You Can. While still in his teens, Abagnale papered the country with bad checks, aided by his brazen posing as a pilot for Pan American World Airways. The disguise allowed him to fly about the country, and later the world, for free, deadheading on other airlines. It also helped him cash bogus checks, the Pan Am uniform lending him an air of authenticity. Abagnale later posed as a pediatrician in an Atlanta hospital. Then he assumed the identity of a Louisiana prosecutor, backed with a fake law degree from Berkeley. He did though pass the bar exam in Louisiana, after three tries.

After being arrested in France and serving time there, followed by a stint in a Swedish jail, Abagnale was extradited to the United States, convicted, and sentenced to federal prison. He didn’t serve long. The FBI approached the con man, seeking assistance in their prosecution of check fraudsters and other business crimes. Abagnale’s association with the FBI led to a career in security, advising banks and other businesses on the subject of the kind of scams he created during his youth. Later investigations by journalists demonstrated that much of his story was exaggerated, a fact which Abagnale admitted. Various sites claim his IQ exceeds 140, and there is no doubt he outsmarted banks and businesses out of millions of dollars. He parlayed that background into an internationally acclaimed consultant in the areas of financial security and bank fraud, a popular lecturer, and a best-selling author.

9. Andrew Cunanan

Over a period of about three months in 1997, Andrew Cunanan gained international notoriety for a series of murders. His victims included a noted Chicago real estate developer, Lee Miglin, and designer Gianni Versace. Cunanan’s known five victims were brutally murdered, after he developed personal relationships with all but one, a cemetery caretaker named William Reese. Cunanan apparently killed Reese simply to steal his truck, which he drove to Miami Beach, Florida. After the murder of Reese, Cunanan’s fourth killing in less than a month, he was placed on the FBI’s Ten Most Wanted List. On July 15, 1997, Cunanan murdered Versace on the front steps of his Miami Beach home.

Cunanan killed himself eight days later, leaving behind no suicide note and little to allow police to determine a motivation for his killing spree. In retracing the murderer’s steps, investigators discovered a man who regularly used drugs including methamphetamine, prescription opioids, cocaine, and marijuana. He also drank heavily, and built relationships with older, well-to-do men from whom he stole their credit cards. He was known as a habitual liar, who exaggerated his accomplishments and created a false background for himself. He also possessed an IQ well into the 140s, as tested in school in La Jolla, California. His intelligence notwithstanding, Cunanan likely suffered from antisocial personality disorder, spending most of his brief and violent life living off the generosity of wealthy, older, gay men.

8. Ted Kaczynski

Ted Kaczynski held the dubious distinction of being the subject of the longest and most expensive search in the history of the FBI before he was finally arrested in 1995. Known as the Unabomber, Kaczynski was a mathematical prodigy who entered Harvard University at the age of 16. His IQ was reported as being 152. While there he excelled in classes, and despite some calling him reserved and withdrawn, others who lived with him at Eliot House claimed he was personable and friendly. While at Harvard he participated in a psychological study in which he was verbally and emotionally abused, his reactions filmed, and the films played back to him at a later time. Some claim he was psychologically damaged from the study. He later earned a doctorate in mathematics from the University of Michigan. After working for a time at the University of California, Berkeley, Kaczynski decided to live “off the grid.”

From a small cabin he built near Lincoln, Montana, Kaczynski struck at the symbols of society which he felt imposed upon him. At first his acts were small time sabotage against encroaching real estate development. In 1978 he began the series of bombings which ultimately killed three people and injured an additional 23. Between 1978 and 1995, 16 bombs, either delivered via the mail or by hand, were attributed to the man who became known as the Unabomber. He also sent letters to newspapers describing his exploits and motivations. He demanded an essay he had written, Industrial Society and its Future, be published to prevent further bombings. When it was, some political scientists compared it favorably to Orwell’s 1984. Kaczynski is serving eight life sentences without possibility of parole in a Supermax prison in Florence, Colorado.

7. Carl Gugasian

The name of Carl Gugasian is not particularly well known outside the circles of law enforcement. An army veteran with special forces training and experience, Gugasian studied for a doctorate in statistics and probabilities from Penn State University. He claimed to make a living gambling. In reality, he made a living robbing banks. Meticulously planned robberies, in which he entered the bank just before closing, usually on a Friday, and always wearing a mask. He particularly favored Freddie Kreuger masks. He selected small banks, bordered by woods, and he studied the area using topographical maps. He fled the scene on foot, into the woods, where he stashed the loot and the maps in plastic buckets or PVC pipes, hidden in the brush. He then rode a dirt bike to a van, loaded it into the vehicle, and leisurely left.

After robbing more than 50 banks, over a period of nearly 30 years, boys playing in the woods stumbled upon one of his many stashes. Over the ensuing months police in multiple states found several more, in the woods near one of the banks he robbed. Gugasian was caught, and immediately cooperated with the police. He cooperated to the extent that his sentence when convicted, which could have been 115 years, was reduced to just 17 years. While in prison he taught mathematics to his fellow inmates in formal classes. He also agreed to make a bank robbery training video for the FBI. He served his sentence in federal prison at Fort Dix, New Jersey, released in 2017. The FBI calls him the most prolific bank robber in American history.

6. Gerald Blanchard

In November 2007, Canadian Gerald Blanchard faced 164 years in prison, over 16 charges of fraud and robbery committed in Canada and internationally. He asked the prosecutors for a deal, based on information he had regarding the Star of Empress Sisi, a pearl and diamond ornament once worn by Elizabeth of Bavaria in the 19th century. The Star had been on display in the Schonbrunn Palace in Austria. Blanchard told Canadian authorities that the piece on display was a replica which he had purchased in the palace’s gift shop days before stealing the real Star. He offered to show the police the real item in return for a reduced sentence. Austrian authorities were aware that the piece had been stolen, but released few details regarding the investigation.

Blanchard told police he parachuted onto the roof of the Schonbrunn Palace in 1998, disabled the alarms, and replaced the Star of Sisi with the replica, all in the middle of the night. The theft wasn’t noticed for a full two weeks, by which time Blanchard was in Canada. He hid the priceless gem in a Winnipeg basement. He knew fencing the piece was impossible, but kept it anyway as a form of insurance. When Blanchard directed the Canadian police to the gem, nine years had transpired since its theft. His sentence was reduced to eight years, and in the end he served but two, with none of his accomplices in his fraudulent activities and numerous other thefts charged for their crimes.

5. Rodney Alcala

In the middle of a two-year killing spree, Rodney Alcala took time out to appear on the television program The Dating Game. He won a date with a young woman named Cheryl Bradshaw, who subsequently refused to honor it, having found him “creepy.” Possibly it was the wisest decision of her life. After his arrest and conviction for several murders which occurred before and after his appearance on the program Alcala became known as the Dating Game Killer. Between 1977 and 1979 Alcala killed at least five women in California, and was subsequently convicted of murders in New York state in 1971 and 1977. According to police, Alcala tortured his victims, strangling them until near death, reviving them, and repeating the process.

Alcala also used his considerable persuasiveness to convince young women and men that he worked as a professional photographer, and collected a “portfolio” of hundreds of young women and teenage boys, in sexually explicit poses, mostly naked. After his California convictions, several states named him as a “person of interest” in unsolved murders, including Washington and Wyoming. A graduate of UCLA who also studied film under Roman Polanski, Alcala’s IQ was said to be “more than 160.” As of this writing he remains incarcerated in California.

4. Hassan and Abbas O

Hassan and Abbas O may have committed the perfect crime when they robbed a German department store of over $6.8 million worth of jewelry. In a robbery straight out of a Hollywood movie, three masked men entered the store in January 2009, through a skylight, sliding down ropes to the seventh floor. After stealing the jewels, the masked bandits used a rope ladder to descend to the ground floor and escaped. They left behind a single latex glove, from which police investigators extracted DNA, which identified two of the men, Abbas and Hassan O, identical twins. Under German law, their last name cannot be revealed. In February police arrested the brothers and charged them with burglary.

According to German law, neither could be convicted, since the DNA established that one of them left the glove, not both. “From the evidence we have, we can deduce that at least one of the brothers took part in the crime, but it has not been possible to determine which one,” ruled the court. The twins decided to keep mum regarding their participation in the crime, understandably. With no other evidence, and with no third suspect, German authorities released the twins on March 18, 2009. The statute of limitations for burglary in Germany is 10 years. During that time, German law prohibited the police from monitoring the brothers’ bank accounts and tapping their phones. The brothers’ only comment regarding the crime was to thank the state for setting them free. They got away with it.

3. Charlene Williams

Charlene Williams and her husband, Gerald Gallego, (also known as Stephen Sykes) killed 10 victims in the Sacramento, California area from 1978 to 1980. Prior to their murder spree Gallego was a career criminal, having racked up 23 arrests beginning at the age of 13. Charlene was married twice before meeting Gallego. She came from Stockton, California, was an accomplished violinist, and possessed an IQ over 150. She and her husband began their murderous rampage in September 1978, when Charlene convinced two teenage girls to accompany her to a van where Gerald waited with a handgun. They abducted the girls, Gerald raped both, and then executed them with a gunshot to the back of their heads.

In June 1979, they abducted another pair of girls from the Washoe County Fair, the remains of whom were not found for two decades. In April 1980, two more girls went missing from a mall near Sacramento. They were murdered in Nevada, bludgeoned to death. At least two other women, both adults, were abducted and murdered by the pair in the summer, 1980. Finally, in November, a witness observed Williams and Gallego abducting an engaged couple as they left a fraternity party. Police traced the license number of the vehicle used in the abduction, though not before the couple had been murdered, in different locations. Imprisoned, Charlene was released in 1997 after completing her sentence. Gerald died in prison in 2002.

2. Richard Loeb

Richard Loeb was the son of a senior executive with Sears, Roebuck and Company. A talented and highly intelligent child, Loeb skipped several grades in school, and possessed an IQ estimated to have been over 150. Skipping grades led to isolation from classmates, since he was several years younger than most of them. As a child he developed a passion for lying and for living a fantasy life as a criminal. In his teens he acted out some of the fantasies, committing petty thefts and acts of arson. At the age of 14, he entered the University of Chicago, where he met Nathan Leopold, three years his elder. Both were gay, and entered into a physical relationship as students. In 1921, Loeb transferred to the University of Michigan. Loeb graduated from Michigan in 1923. He was 17, the youngest graduate in the school’s history.

In 1924 Loeb returned to Chicago for graduate work, reunited with Leopold, and convinced him to join in a murder for the thrill of the crime. Their victim was 14-year-old Bobby Franks, a cousin of Loeb’s. After killing the boy, the pair sent a ransom note to his father, who contacted the police. The murder and subsequent trial of the pair was a national sensation, with Clarence Darrow giving an impassioned summary for the defense, arguing against the death penalty. Loeb was sentenced to life plus 99 years. While serving his sentence at Stateville Penitentiary in Joliet, Loeb propositioned another inmate, in January 1936. The inmate, James Day, claimed that Loeb had attempted to molest him in the shower, and he responded by stabbing him. Day was acquitted of charges of murder.

1. Nathan Leopold

Nathan Leopold, the other half of the murderous Leopold and Loeb duo, possessed an IQ believed to be about 200. He entered the University of Chicago at the age of only 15, expressing deep interest in ornithology. He became enthralled with the younger Loeb, who found the older boy easy to manipulate, due to his lack of friends and social ineptitude. Leopold later expressed reluctance to join Loeb in the murder of Bobby Franks, and claimed the fatal blow to the boy (Franks was beaten to death with a chisel) was struck by Loeb. At their trial, Loeb made the opposite claim. Sentenced to the same terms as Loeb, Leopold served his time at Stateville Penitentiary, though he avoided the fate which his partner suffered. Instead, Leopold volunteered for medical experiments conducted by the University of Chicago and the United States Army, to discover new treatments for malaria during World War II.

Leopold was deliberately inoculated with malaria, and later volunteered to work in the study, first recruiting other volunteers. Later he monitored experiments, and wrote reports on their results. Prison officials, Army officers, and University of Chicago scientists reported favorably on his work during the study. In 1958 Leopold was released from prison and eventually went to work as an X-Ray technician at the Castaner General Hospital in Puerto Rico. He earned a master’s degree from the University of Puerto Rico and taught there, while doing research into leprosy at the University Hospital. In August 1971, he died of complications of diabetes in Puerto Rico. During his lifetime he learned to speak five languages fluently, obtained several degrees, wrote at least two books, and earned eternal infamy as one half of the notorious Leopold and Loeb.

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