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.
Now, it is reckoning time for Joaquin "El Chapo" Guzman, who will go on trial Monday in New York and faces life in prison if convicted of charges that for 25 years he flooded the United States with tons of cocaine, marijuana, heroin and methamphetamine.
While in prison for nearly two years Guzman, 61, 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 the hearings he has attended in US federal court, the judge has not even allowed him to speak.
"I have headaches every day. I vomit almost every day. I need work done on two molars and they hurt a lot," Guzman said in his only direct communication with Judge Brian Cogan in a letter sent in February.
He complained that his jail cell is always either too cold or too hot. "It is torture, 24 hours a day," wrote 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 legendary 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 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 they had and 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 "very humble, very poor" and that his mom 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.
Lovestruck 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.