10 Crime Bosses Who Maintained Power in Prison

Salvatore Riina[a]

Sicilian Mafia
In 1986, the Maxi Trial in Palermo handed Salvatore “Totò” Riina a life sentence in absentia. It would be nearly seven more years before the Sicilian Mafia chief was captured. But this would not be the end of his notoriously cruel rampage. The detained Riina and other bosses ordered a series of terrorist attacks to assassinate or intimidate witnesses. He also ordered more strategic hits, including the kidnapping and eventual murder of an informant’s 12-year-old son. Riina’s criminal career finally came to an end when he was moved to solitary confinement for the remainder of his life. Until then, the brutality that could only be contained by extreme measures earned him the nickname “La belva”–“The Beast.”

Rayful Edmond[b]

Independent
Drug kingpin Rayful Edmond III was key to the expansion of the crack epidemic into Washington, D.C. The resulting violence earned the city the reputation as the “murder capital of the U.S.” Edmond’s conviction in 1990 merely provided business opportunities. He collaborated with fellow high-profile inmates at the Lewisburg Federal Penitentiary to continue trafficking. When he was caught in ‘96, 30 years were added to his life sentence. Though the oversight and this gesture were scandalous, Edmond became a government informant to protect his mother. After multiple arrests and years in witness protection, he died shortly after being released in 2024. Despite some good coming out of Edmond’s second downfall, there's no accounting for damage he caused even locked away.

Lawrence Bishnoi[c]

Bishnoi Gang
Much of the story of the Bishnoi Gang takes place behind bars. The namesake was a petty criminal who cultivated connections in jail in the early 2010s. By the time he was finally sent to prison in 2014, Lawrence Bishnoi had built an empire well beyond Punjab. He then continued to lead some 700 associates in international smuggling, murder and political corruption. He became something of a celebrity in 2018, when he made a press statement threatening actor Salman Khan outside of a courthouse. Continued operations even after multiple transfers haven't curbed that hubris. Once an ambitious student from an affluent family, Bishnoi is an alarming testament to what a great mind is capable of in prison.

Vincent "The Chin" Gigante

Genovese Crime Family[d]
This low-level enforcer was in and out of jail before his 1959 conviction only strengthened bonds with cellmate Vito Genovese, the mentor he aided in his takeover of the Luciano Family two years prior. Vincent “The Chin” Gigante went on to become a powerful New York boss who evaded trial with public displays of mental unfitness. After the ruse fell apart in 1997, he continued to run the Genovese Crime Family from prison. Andrew Gigante acted as his father's attache until they were both indicted on racketeering and obstruction charges in 2002. The Chin’s shocking guilty plea formally put an end to a criminal career that spanned decades, and sometimes thrived in prison.

Carmine Persico

Colombo Crime Family
Nicknamed “Immortal,” Carmine Persico was practically unstoppable as boss of the Colombo Crime Family. He was believed to still be in charge after he began his tenure in prison in 1973, before receiving a permanent sentence in ‘86. Persico collaborated with John DeRoss[e] then, and after the latter’s release in the wake of the third Colombo War. What followed was years of power struggles and restructuring under Persico’s supervision. A government informant even testified that he took contracts out on the FBI agents and prosecutors responsible for his imprisonment. Though the open secret of his influence reportedly declined through the years, Persico was the official boss of the Colombo Family from 1973 to his death in 2019.

Raffaele Cutolo[f]

NCO
Raffaele Cutolo’s run with Neapolitan street gangs ended when he was incarcerated for murder in 1963. That was really just the beginning of his criminal career. The young rogue’s charisma and business instincts cultivated a huge following among inmates. As they carried Cutolo’s influence beyond prison, the Nuova Camorra Organizzata became one of the most sophisticated and powerful syndicates in Italy. But after the organization was devastated by gang wars, Cutolo was effectively removed from his network after being transferred in ‘93. By then, his defiance of the penal system was so notorious that it inspired the fictional novel and film “The Professor,” titled after Cutolo’s nickname. The true story is a chilling enough portrait of a violent mastermind with nothing to lose.

Anthony "Gaspipe" Casso

Lucchese Crime Family[g]
Even for New York organized crime, Lucchese underboss Anthony “Gaspipe” Casso was considered sadistic. That came back to haunt him after his arrest in 1993. While detained at the Metropolitan Correctional Center, Casso arranged escape plans and hits. His orders became so reckless that the family ultimately severed ties. Casso thus became an informant for the FBI to protect himself at many colleagues’ expense. However, the plea deal was nullified by his lack of honesty and cooperation with authorities, as well as continued criminal activity. Casso was sentenced to 455 years in prison in ‘98, having burned all his connections by trying to keep them inside. He died in 2020 after failing to secure compassionate release.

Joaquín "El Chapo" Guzmán

Sinaloa Cartel
The legend of Joaqúin Guzmán’s power was cemented by his stints in prison. His leadership of the Sinaloa Cartel made him one of the world’s most powerful criminals before he was sent to prison in Mexico in 1993. There, El Chapo delegated his organization to greater power, and enjoyed a lavish lifestyle by bribing guards. They eventually let him walk out of prison in 2001. He was arrested again thirteen years later, detained under strict security, and escaped again through a tunnel. His 2016 arrest and subsequent extradition to U.S. federal custody finally put an end to his influence. El Chapo’s story being unlike any in organized crime, it took a lot to truly lock him away.

Charles "Lucky" Luciano

Luciano Crime Family
In 1936, the boss of the Luciano Family seemingly ran out of luck when he was sentenced to up to five decades in prison. In fact, Charles “Lucky” Luciano’s influence went a long way over the next decade. He made orders through acting bosses and acquired luxurious amenities, including a personal chef. It was only after a failed appeal two years later that he stepped down from his position. However, with World War II raging, the Navy tapped Luciano and his organization to help secure the New York waterfront and provide contacts in Sicily. In exchange, Luciano received deportation to and relative freedom in Italy in ‘46. Even in apparent defeat, the father of the modern mafia was an effective negotiator.

Pablo Escobar

Medellín Cartel
Pablo Escobar’s influence was such that he could control his own downfall in 1991. He negotiated his surrender to the Colombian government on the condition that would only serve five years in a prison he himself designed. Escobar even hand-picked his guards at La Catedral[h], nicknamed “Hotel Escobar” for its luxuries. The cozy deal required the Medellín Cartel leader to cease all criminal activities. But, of course, it was business as usual under the security of government corruption. Escobar’s official incarceration was really just to prevent extradition to the U.S. and protect him from enemies. Following media reports of torture and murder at La Catedral, Escobar escaped to avoid transfer to a legitimate prison, and died in a police pursuit in ‘93.


Who are some other criminals whose influence couldn’t be locked up with them? Testify in the comments.

[a]salva-TORE-ray REE-nah https://youtu.be/Q5rVrMwkeMc?si=63GsXMDOxwYGonH6&t=1

https://youtu.be/Lb_dBYkVVCI?si=RSESdqHcpj6Cr7MC&t=95
toto https://forvo.com/search/Tot%C3%B2/
https://forvo.com/search/belva/
[b]https://youtu.be/M25lQREIyrY?si=LfFaU39lfEIUPcde&t=3
[c]BISH-noy / bih-noh-ee https://youtu.be/ZtTUbBEAEAg?si=PhcXnAcg3oEeeHKm&t=2
PUN-job https://forvo.com/search/Punjab/
[d]jig-GAN-tee https://youtu.be/OO_BBdn7ecE?si=GVN-P8ItbaQv-Nhq&t=11
jenna-VEEZ
[e]https://youtu.be/73DclXJLBtA?si=oUvR032tTGgaAkK6&t=54
[f]rahffa-ELLEH COOTA-loh https://youtu.be/rSypb6cpUzc?si=L6Z9p7Vu5-h1wyxc&t=74 https://youtu.be/T8aefoveoyA?si=ELBy5gy6tYYRXhJF&t=4
NWHOA-vah cah-MORE-ah ore-gan-neet-ZATTA https://youtu.be/T8aefoveoyA?si=oL4LJL0ltP0ugbHm&t=6
[g]https://youtu.be/yZJa0n0Zi4M?si=wO5SIA10Z7IANpJ7&t=18
loo-KAY-zee https://youtu.be/Mb145VG9Hec?si=CFRWAEAMuZqhStic&t=90
[h]cat-ay-DRAL https://translate.google.ca/?sl=es&tl=en&text=La%20Catedral&op=translate