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He'd owned a number of businesses, including automotive body shops, but by November 2008 he was "nearly broke" and looking for investors to help him build an apartment complex in Guadalajara.
That's why he'd approached his old acquaintances Pedro and Margarito Flores. Vasquez-Hernandez knew the twins had money.
He also knew they made it by trafficking cocaine and heroin from Mexico into the United States.
Instead of convincing them to buy into the apartment project, Vasquez-Hernandez says the brothers talked him into helping them move the coke. Then, while he was making the arrangements, another acquaintance fronted 76 additional kilos that the Flores brothers agreed to sell on his behalf.
It didn't go as planned. Vasquez-Hernandez says he never collected the $2.2 million he was owed.
And that turned out to be the least of his problems, because the Flores brothers were secretly cooperating with the U.S. government. A few months later Vasquez-Hernandez was indicted for participating in a drug conspiracy. He pleaded guilty to some of the charges in federal court in Chicago last April.
"I am ashamed of my actions," he wrote in a letter to the court last month.
But U.S. officials say this is not a case of a bumbling businessman who made a dumb mistake.
Citing sworn statements from the Flores twins, the feds accuse Vasquez-Hernandez of being a top operative for the Sinaloa cartel who's known as "Alfredo Compadre." They also say he's a close friend of its former leader, Joaquin "El Chapo" Guzman, who was captured earlier this year by Mexican authorities.
The competing images of Vasquez-Hernandez, 59, will be presented to federal judge Ruben Castillo during a hearing Monday afternoon to determine how long he's going to serve in prison. His attorneys argue that he should get no more than ten years. He's eligible for as much as life.
The outcome will depend largely on how reliable the judge finds the testimony of the Flores twins, who have told government officials they were major distributors for the Sinaloa cartel from 1998 until they began cooperating with the government in 2008.
In statements they gave in June 2009 that were unsealed earlier this month, the brothers described the cartel's methods for moving cocaine from Central America, and heroin and marijuana from Mexico into Chicago, their U.S. distribution hub.
They said they learned from Vasquez-Hernandez and others that Sinaloa owned cargo planes that took clothing on "humanitarian" missions to Central and South America and returned to Mexico packed with cocaine.
"The planes would land at Mexico City International Airport and Chapo would then use his contacts to have the cocaine offloaded from the planes and get the cocaine out of the airport," Margarito Flores told authorities in his statement.
In other instances, coke was smuggled into Mexico on trucks, trains, fishing vessels, cargo ships, and even submarines "used to evade law enforcement and the military when moving cocaine across the open ocean," according to Pedro Flores. The cartel would then get it across the U.S. border by rail, truck, or underground tunnel.
The Flores twins say Vasquez-Hernandez helped coordinate the entire operation.
"Alfredo told me that he was a lifelong friend of Chapo's and was godfather to Chapo's son Alfredillo," Pedro Flores said in his statement. "Alfredo told me that he handled logistics for Chapo."
From Chicago the brothers served wholesale customers in cities from Vancouver to New York. By 2007 the twins were distributing 1,500 to 2,000 kilograms of cocaine and multiple kilograms of heroin each month, most of it transported on semi trucks with secret compartments in the roofs.
And they said Vasquez-Hernandez and his wife were helping them do it by operating an importing company that served as a front for their drug business.
Vasquez-Hernandez discussed the details of Sinaloa's network during their meeting in early November 2008, they said—and Pedro Flores secretly recorded it.
But the recording was muffled and hard to make out. A transcript of key parts of the conversation that was including in court filings is peppered with "U/I," for "unintelligible."
Vasquez-Hernandez's attorney, Paul Brayman, maintains that one of the Flores brothers was actually the person caught on tape discussing Sinaloa's transportation network.
Brayman also argues that the twins are hardly reliable sources. Among other things, he alleges that they continued to distribute cocaine and collect millions of dollars in proceeds after they began cooperating with the feds.
In June 2009, while in federal custody, Pedro Flores arranged to purchase his wife a $100,000 Bentley for her birthday, Brayman says.
"The Flores brothers have absolutely no allegiance to the Court, its oath, or anyone aside from themselves," Brayman argued in a filing last week. "They are completely incredible."
The twins have cut their own deals with the government—the terms of which could be unsealed as soon as Monday.