But Guzman's latest cat-and-mouse game with the authorities reached the end of the tunnel yesterday when he was recaptured by marines on his home turf in the northwestern state of Sinaloa, President Enrique Pena Nieto declaring triumphantly: "Mission accomplished."
Before that, the man whose old nickname means "Shorty" had used the money from a drug empire whose tentacles reach Europe and Asia to dig himself out of trouble again and again.
US and Mexican authorities have regularly discovered sophisticated tunnels with rails and electricity used to ship marijuana, cocaine and other drugs into the United States, with cash and weapons coming the other way.
The 58-year-old Sinaloa drug cartel leader's legend soared after he humiliated authorities by escaping prison in his most ambitious tunnel yet.
Also Read
On July 11, 2015, after just 17 months at the Altiplano prison in central Mexico, Guzman slipped through a hole in his cell's shower, climbed on a motorcycle mounted on rails, and traveled 1.5 kilometers (one mile) through the tunnel.
Marines nearly captured him in October in a remote mountain region. Authorities said Guzman injured his face and a leg while falling in the rough terrain, but special forces failed to nab him.
AFP journalists who visited the area weeks after the operation found bullet-riddled homes and cars. Residents said military helicopters fired on the community during the operation, prompting hundreds to flee.
He had been on the lam for 13 years after escaping a first time in 2001 from another prison by hiding in a laundry cart. He had spent eight years in prison following his 1993 capture in Guatemala.
Guzman became a legend of Mexico's underworld, with musicians singing his praises in folk ballads known as "narcocorridos," tributes to drug capos.
He is said to have been brazen enough to walk into restaurants in his state of Sinaloa, ask diners to hand their cell phones to his bodyguards, eat calmly and pay everyone's tabs before leaving.