There is a reason why thrillers and police procedurals are so popular on TV and in literature: We all love a good mystery to solve. Detectives pour over information, interviews, and clues, building a puzzle of what-ifs and alibis until it all slots perfectly into a neat, completed puzzle, and the big picture becomes clear. Law enforcement uses all kinds of techniques to track down the bad guys, but sometimes, even those advanced tricks aren’t enough, and the case becomes somewhat impossible to solve.
It is very handy in these circumstances to think like a criminal and have insights into an operation or just the underworld in general. Basically, you need a criminal. Here are ten hardened criminals that helped police crack hard-to-solve cases.
Related: Top 10 Notorious Father-Son Mafia Combos
10 Paul Skalnik
Sent to jail for passing bad checks, draining his wife’s accounts, and exhausting her credit cards, Paul Skalnik has spent many years in and out of jail. In fact, Skalnik is known as one of the most prolific prison informants ever.
He first became an informant when police wanted information on the Moody Park Three (anti-police-brutality activists who incited a riot). He testified in court that the accused had confessed to him, leading to their conviction. Since then, Skalnik supplied information in some 37 other cases between 1981 and 1987.
His most contentious involvement, however, is from his role in the conviction of James Dailey, who was accused of murdering Shelley Boggio without any forensic evidence linking him to the crime. Instead, they relied on the testimony of three inmates, one of which was the infamous Skalnik.[1]
9 Sammy Gravano
Salvatore “Sammy the Bull” Gravano, born into the golden age of the mob, was a notorious mobster who got his nickname at an early age when he fought two older boys over his bike. From there, it was one-way traffic to the mafia.
For decades, Gravano was a mobster of note and Gambino Family underboss, participating in hits and enforcing mob rule like only a true mobster can. But with any organization, there is tension, and a regime change bundled infamous mob head John Gotti and Gravano into racketeering charges, which Gotti blamed on Gravano. Feeling betrayed, Gravano agreed to break the one rule enforced by death: He would testify against Gotti.
With Gravano’s testimony, there was enough evidence to convict not only Gotti—the infamous Teflon Don—but also forty other mobsters in one of history’s greatest organized crime crackdowns. Living to tell the tale. Sammy the Bull even has his own podcast.[2]
8 Frank Abagnale
Probably the most famous on the list thanks to the 2007 film Catch Me if You Can starring Leonardo DiCaprio, Abagnale is famous for his history of forging fraudulent checks and cashing in on them to the tune of millions of dollars.
Between the ages of 16 and 21, it is believed that Abagnale impersonated a Pan Am pilot to score free flights, masqueraded as a lawyer, and even posed as a medical doctor (although some of his assertions are disputed). However, it was in the check forgery department that Abagnale made a name for himself and which ultimately landed him in jail for 12 years.
Abagnale is also famous for escaping from prison but was returned to serve out the remainder of his sentence (four years). In exchange for a shortened sentence, Abagnale agreed to help the federal government (without remuneration) by teaching law enforcement agencies and has been involved with the FBI for over 35 years. He is considered one of the foremost authorities in securities and check fraud.[3]
7 Frank Lucas
Also immortalized in a film by Denzel Washington, Frank Lucas was a drug kingpin in the 1970s. His drug of choice was heroin. It’s not every man that can go into competition with the mob, especially with something as sophisticated as a drug ring. Still, Lucas found a way, raking in almost $1 million per day from the trade.
Lucas used the coffins of the bodies of dead soldiers returning from Vietnam to smuggle the drugs into America and then sell them here on the streets. However, in the end, it all came crashing down when he was arrested and sentenced to 70 years for his crimes.
Lucas had his sentence reduced on the basis that he turned police informant, which he did, most notably against a corrupt part of law enforcement, the Special Investigations Unit of the NYPD. Fifty-two out of the 70 members of the SIU were eventually jailed or indicted.[4]
6 Kevin Mitnick
Mitnick was on the most wanted list when it came to hacking, circumventing cyber security, and stealing computer code from companies. These were the crimes for which he pleaded guilty and spent almost five years in jail. It is estimated that his shenanigans cost the target companies (Nokia, Sun Microsystems, and Motorola, among others) around $300 million.
Mitnick was released from jail and shortly after found himself in front of the U.S. Senate Committee on Governmental Affairs, having to explain himself. So began his path to something that resembles redemption.
Putting his talents to good use, Mitnick started a consultancy firm and utilized his skills as a cybersecurity expert rather than attempting to circumvent securities systems for his own entertainment.[5]
5 Frank Calabrese Jr.
Frank Calabrese Sr., the father of Frank Calabrese Jr., was sentenced to life in prison and ordered to pay $24 million, plus payment of restitution to the families of the murder victims, for his involvement in a racketeering conspiracy that included murder. What makes this case so fascinating, however, is that his son, Calabrese Jr., was the one who ultimately threw him under the bus.
It was in a prison in Milan that Calabrese Jr., while locked away with his father for a loan shark scheme, turned a corner. He wanted out of the mob life for good. Calabrese Jr. penned a letter in which he shared his willingness to cooperate in keeping his father behind bars. That got the ball rolling.
Calabrese Jr. eventually agreed to wear a wire so that conversations with his father could be recorded. Calabrese Sr., in a fit of rage, started spilling the beans. In a trial where the government had more than 600 exhibits and relied on the testimony of over 100 witnesses, Calabrese Sr. and his accomplices were found guilty.[6]
4 Wayne Bradshaw
Wayne “Big Chuck” Bradshaw is known as the only biker outlaw ever to become a sworn police officer after years of gang-related activities.
It was in the U.S. Army at a base operation in Germany, where regular fist fights were part of his life that he became disillusioned with the system. Upon his return to the U.S., he joined the Pagans motorcycle gang and worked his way up.
It was after he smashed a man’s face in at a bar known as the “Bucket of Blood”—a place where they got into fights regularly—that he realized the life of violence did not suit him. So he did a 360, turned his life around, and became a cop. Bradshaw eventually retired a hero with 20 years of criminal takedowns under his belt.[7]
3 Joseph Valachi
Unofficially, Joseph Valachi was the first man to openly acknowledge the Italian-American mob, as we know it today, exists. He was first a member of Salvatore Maranzano’s crew before he became a member of the Genovese family of criminals. There, Valachi was a crucial part of their operations and had an in-depth knowledge of how they functioned.
A ruthless murderer and leg-breaker for the mob, he was locked up for a drug charge and would spend 15 to 20 years behind bars. That was when he reconsidered his life choices. After getting on the wrong side of Genovese and beating to death a man he wrongfully thought was there to assassinate him, Valachi turned state witness.
Valachi made public the Italian term “Cosa Nostra” (“Our Ting”) and told of how he received the Death Kiss, sealing his fate. In the end, Valachi cemented the existence of the mob in the public eye and broke ground for the Feds as they now knew how the mafia operated.[8]
2 Kenyel William Brown
A thug in the flesh, involved in the drug trade, assault, and numerous violent crimes with guns, Kenyal Brown was also a seasoned informant with all the connections and info the police could possibly want.
After Brown’s first arrest, he served time, after which he was released on parole. On his time out on parole, Brown had at least seven violations, most of them due to missing or failing drug tests and drunk driving charges. He was arrested again, but under federal order, they released him.
Brown provided information on a local street gang involved in narcotics. However, Brown was implicated in multiple homicides, which included six deaths in three cities, two carjackings, and a nonfatal shooting, so he was deactivated as an informant, and the mission was considered an utter failure.
Brown committed suicide while fleeing from the police.[9]
1 John Martorano
John Martorano was a hardened criminal and hitman who served only 12 years in prison for admitting to killing 20 people after he struck a deal and decided to cooperate with prosecutors.
Martorano was asked to testify against James “Whitey” Bulger, his old partner in crime, who was charged with participating in 19 murders during the ’70s and ’80s, as well as extortion, drug trafficking, and running illegal businesses.
The crazy thing about Bulger was that he himself was an FBI informant. In fact, that was the main reason why Martorano decided to become an informant in the first place. Heartbreak. Betrayal. All the things that could get you killed in the mafia world. Bulger was found guilty and sentenced to life.[10]
