As a child living in poverty in Mexico, he peddled fruit just to eat. A lifetime later, as the world's most wanted drug lord, his empire was so vast he commanded a fleet of submarines to move his wares.
But having been convicted in February for flooding the United States with tons of cocaine, marijuana, heroin and methamphetamine over 25 years, Joaquin "El Chapo" Guzman will now be sentenced in New York on Wednesday.
Prosecutors have requested life imprisonment, plus an extra 30 years for good measure.
While in prison for the last three-and-a-half years Guzman, 62, has lost much of the aura of the feared and, for many in Mexico, beloved drug kingpin he once enjoyed.
He lost weight and says he has health problems. Guzman's head is shaved and he wears humble blue prison garb. His trademark moustache is gone.
In May, his lawyers complained that his detention in solitary confinement in a high-security prison in Lower Manhattan violated the constitutional ban on "cruel and unusual punishment."
"Mr Guzman has been over two years now without any access to fresh air or natural sunlight," his lawyers said, adding that he'd "been using toilet paper as makeshift earplugs."
It has been a humiliating fall from a position of power and lifestyle of luxury for Guzman, whose nickname "El Chapo" translates as "shorty," due to his five-foot, two-inch (1.57-meter) frame.
In his heyday, the man towered over his rivals, casting a long shadow over Mexico's criminal underworld.
During Guzman's reign, his Sinaloa drug cartel's empire expanded across the globe, its tentacles stretching from the Americas to Europe and Asia.
After two prison breaks, Guzman was finally captured by Mexican marines in January 2016 and extradited to the United States in January 2017, ending his decades-long cat-and-mouse game with the authorities.
While his cartel is synonymous with violence and drug addiction, Guzman became a hero of Mexico's underworld, with musicians singing his praises in folk ballads known as "narcocorridos" -- tributes to drug capos.
He fooled the government with his cartel's engineering feats, building tunnels to ship drugs under the US-Mexico border and to help him escape the authorities.
While he nurtured a Robin Hood image back home, his cartel fought bloody turf wars with rivals, contributing to the drug conflicts plaguing Mexico.
Guzman grew so rich that he was on Forbes magazine's list of billionaires, but he dropped out in 2013 after spending much of his wealth on protection.
- 'Very poor' -
"I supply more heroin, methamphetamine, cocaine and marijuana than anybody else in the world. I have a fleet of submarines, airplanes, trucks and boats," Guzman boasted to Sean Penn in a clandestine meeting that the US actor wrote about for Rolling Stone magazine in 2016.
Guzman said in a separate video message to Penn that his family was once "very humble, very poor" and that his mother made bread in the village of La Tuna.
"I sold oranges, I sold soft drinks, I sold candy," he said, claiming he entered the drug business at age 15 because there were "no job opportunities."
"The only way to have money to buy food, to survive, is to grow poppy, marijuana, and at that age, I began to grow it, to cultivate it and to sell it," he said.
Guzman was born on April 4, 1957, in Badiraguato, a town known as the cradle of several drug lords.
He was recruited by Guadalajara cartel boss Miguel Angel Felix Gallardo, known as "The Godfather" of Mexico's modern drug cartels.
After Felix Gallardo was arrested in 1989, Guzman's Sinaloa cartel began its meteoric rise.
But he had enemies.
A gunfight in May 1993 at the airport of Guadalajara ended the life of the western city's archbishop, Cardinal Juan Jesus Posadas Ocampo, allegedly because he was mistaken for Guzman.
He was arrested in Guatemala in June 1993. Eight years later, he pulled off his first prison break, sneaking out inside a laundry cart in 2001.
- Love-struck capo -
It took 13 years for the authorities to grab him again, in February 2014, in a condo in the Sinaloa resort of Mazatlan, where he was hiding with his wife, Emma Coronel, and their US-born twin daughters.
But 17 months later, Guzman fled again, humiliating President Enrique Pena Nieto's administration.
This time, his henchmen had built a one-mile (1.5-kilometer) tunnel that opened in his cell's shower. He zoomed out by hopping on a modified motorcycle mounted on rails.
But it only took six months for the marines to catch him again in Los Mochis, a coastal town in Sinaloa.
Officials say his soft spot for Mexican-American actress Kate del Castillo led to his downfall.
Mexican officials leaked to the media phone intercepts of his flirtatious text messages to the star, who brokered Guzman's meeting with Penn.
Guzman married at least three times. He has several children, including two sons accused by the US authorities of having "significant" roles in the Sinaloa cartel. Another son, Edgar, was shot dead in 2008.