The logistical problem for his keepers: The case is being prosecuted across the East River in federal court in Brooklyn.
Guzman was extradited to the United States from Mexico on 19 January 2017, after escaping twice from Mexican prisons. He faces life in prison if convicted. But at what price?
"It's probably set up to be the most expensive trial in the history of the US", said Rob Heroy, a North Carolina lawyer who has defended other Mexican drug barons.
After Felix Gallardo was arrested in 1989, Guzman's Sinaloa cartel began its meteoric rise.
The Sinaloa cartel that Guzman founded in 1989 is still hugely powerful and his co-defendant Ismael "El Mayo" Zambada remains at large.
It is alleged that he spent a quarter of a century smuggling more than 155 tonnes of cocaine into the United States. In 2016, an average of 174 Americans died every day from drug overdoses.
No jurors have yet been chosen, and the selection process is expected to continue on Tuesday.
US District Judge Brian Cogan, prosecutors and defence lawyers on Monday questioned 45 potential jurors, rejecting 17.
The 12 jurors, with six alternates, will remain anonymous and will be escorted by USA marshals to and from court every day. The eventual panelists will be escorted to and from the federal courthouse by federal marshals.
According to the indictment, Guzman is responsible for ordering thousands of murders during the years his Sinaloa Cartel funneled 200 metric tons of cocaine as well as other drugs into the United States, pulling in $14 billion (€12.3 billion).
USA prosecutors say that as the head of the Sinaloa Cartel since 2003, Guzman directed the movement of multi-ton shipments of drugs including heroin, cocaine, marijuana, and methamphetamine across borders and into the United States. Some are expected to testify under aliases.
The trial, which one expert says will cost the U.S. taxpayer more than $50m (£38m), will hear several hundred witnesses testify. Even Guzman's lawyers are in the dark as to all the former associates, hired hands or rivals who have turned informants.
Some of the informants have already been absorbed into the U.S. witness protection programme and given new identities and homes around the country.
An anonymous pool of potential jurors - gleaned from 1,000 New Yorkers who were sent a 31-page questionnaire - will arrive in Brooklyn federal court, where they will lay eyes on the runty drug baron himself as they are probed as potential panelists at Guzman Loera's trial on drug-conspiracy charges.
After Guzman was brought to NY, authorities here decided he should be housed in solitary confinement in a high-security wing of a federal jail in Manhattan that has held notorious terrorists and mobsters. He spends 23 hours a day in his cell.