Criminal Helpers: 5 Famous Ex-Cons Who Switched Sides

What’s the old saying – “It takes a thief to catch a thief”? Well, it seems the same is true for computer hackers, forgers, and even mob bosses. While criminals and the organisations that are meant to catch them don’t typically make for a good match, some ex-cons are given an ultimatum: work for the very agency that wants to put them behind bars or face the threat of prison. If given the choice, many pick the former.

Hollywood loves these salvation stories and the role of the criminal-turned-informant is a familiar trope in popular television shows like White Collar and The Blacklist as well as hacker-turned FBI agent Penelope Garcia on Criminal Minds. (these are all hyper-American, need to find more British examples?) Catch Me If You Can…

Man of Steel actor Henry Cavill takes on the role of Napoleon Solo – a former criminal-turned-CIA agent in the upcoming film remake 1960’s TV spy classic The Man from U.N.C.L.E. Set during the Cold War, Cavill, alongside Armie Hammer in the role of ex-KGB operative Illya Kuryakin, work to take down a massive international criminal operation which aims to destabilize the fragile balance of power through the proliferation of nuclear weapons and technology.

To celebrate the character of Napoleon Solo in the August release of The Man from U.N.C.L.E, we’re taking a look at some of the most famous real-life criminals who went on to work for federal agencies.

Frank Abagnale Jr.

Perhaps the world’s most famous con man, forger and imposter, Frank Abagnale Jr. began his life of white collar crime when he moved out of his family home at the age of 16. One of his earliest tricks included writing personal checks on an overdrawn account – until the bank realized what he was doing. Abagnale spent the next few years opening bank accounts under different pseudonyms and learning to forge checks while evading police custody multiple times – all before the age of 21. Abagnale also managed to successfully impersonate a pilot, paediatrician, and lawyer without ever having set foot in a university. Some of his impersonations lasted months before he was discovered. At age 21 Abagnale was arrested by the French police and would go on to serve time in French, Swedish and U.S. prisons. However, only 5 years in to his 12-year sentence in the U.S. he was released by the federal government on condition that he help the authorities to investigate crimes committed by other fraud and scam artists. Abagnale worked for the Federal Bureau of Investigation (FBI) for more than 30 years as a foremost authority on document fraud, forgery, check swindling and embezzlement. He also opened his own company Abagnale & Associates in order to educate others on how to avoid becoming victims of fraud. Abagnale’s semi-autobiographic book Catch Me If You Can was made into a film of the same name in 2002 starring Leonardo DiCaprio as Abagnale.

Max Ray Butler
Known online as “Iceman” or “Max Vision”, Max Butler created one of the Internet’s largest cybercrime commerce sites, with thousands of users, and ran it out of his San Francisco apartments. Prior to this, however, Butler was an FBI informant. He began as a typical 1990s computer whiz kid, acutely aware of how to detect the weak spots in corporate and bank online security. He made a name for himself finding and securing the financial information of millions of people, amassing millions more than that in dollars on the black market. He was able to do this by gaining several contracts with companies to intentionally break into computer networks to test their security systems. While he was penetrating the networks and writing programs to close the breaches, he secretly left open a back door that would allow access later. Butler would then go back in and collect the information of their clients. When agents showed up at his home in 1998, Butler willingly confessed. The FBI told Butler he could make amends if he worked for them as an informant. He did it, of course, but quickly found himself trapped by the federal agency and was even forced to provide information on a friend. Butler remained an informant for less than a year before he started missing appointments and ignoring FBI phone calls. Butler was arrested and sentenced to 18 months at Taft Correctional Facility in California. Butler was broke when he was released in 2002 so he went on to establish the Internet site “Cardersmarket” in 2005. The business became a clearinghouse where hackers could buy and sell credit card numbers and trade expertise. Butler never returned to FBI service and is currently serving a 13-year sentence for his role in the online company.

James “Whitey” Bulger

“James “Whitey” Bulger is perhaps Boston’s most notorious gangster. He rose through the criminal ranks in Boston before eventually gaining control of the poor Irish area of South Boston. By 1979, Whitey Bulger had become a preeminent figure in the organized crime scene and worked closely with the notorious Winter Hill Gang. That year, leader Howie Winter was sent to prison for fixing horse races, and Bulger assumed the gang’s leadership. Over the next 16 years, he came to control a significant portion of Boston’s drug dealing, bookmaking, and loan sharking operations. However, little known to the members of his gang, Bulger was acting as an FBI informant in order to take down the Patriarcas, a New England organised crime family, while simultaneously building a more powerful and more violent crime network of his own. Bulger continued to provide information to the FBI until the early 90s, but was soon informed by a childhood friend who worked as an FBI agent that the agency had in fact been looking into Bulger’s own criminal activities. Bulger went in to hiding and remained on the run from the FBI until his recent arrest in 2011 at the age of 81. Black Mass, a film based on Bulger’s life and criminal activity will be released later this year with Johnny Depp in the starring role.

Ana Cumpănaș

Also known as Anna Sage or the Woman in Red, Ana Cumpănas was an Austro-Hungarian born Romanian prostitute and brothel owner in the American cities of Chicago, Illinois and Gary, Indiana. She is best known as the federal informant who assisted the FBI in tracking down notorious criminal John Dillinger. As a brothel owner, she knew Dillinger because he ran in her circle of shadier companions in Chicago. However, federal authorities considered her an “alien of low moral character” based on her career choice and forced her to face the reality of deportation back to Romania. To avoid this fate, Cumpănas pointed the finger at Dillinger in order to obtain permanent residence in the United States. Her association with FBI agent Melvin Purvis would lead to the eventual shooting of Dillinger outside the Biograph Theater in Chicago.

James Kosta

James Kosta was a teenage hacker who by the age of 13 was making $1,500 a month as an IT consultant before legally divorcing his parents. At 14 he used his computer skills to become a low-level hacker, even managing to hack into business and military sites. Through his skill and young age, Kosta quickly gained recognition in the hacking community. That same year he was arrested by the FBI and charged with 45 counts of technical burglary and as he was being tried as an adult, was sentenced to 45 years in prison. Fortunately for Kosta, the judge took pity on him and sentenced him to a single year in juvenile detention, along with a suspended sentence and a chance to join the military once he was 18 if he committed no further criminal acts. He took the offer and became an intelligence analyst for the United States Navy. By the age of 20 he was working for the CIA, tracking the funds of Warlords in North Africa and the Middle East. In 1999 he started one of the first commercial websites focused on financial markets and sold it for tens of millions of dollars. Kosta is living proof that if given a chance, criminals can turn their lives around.