Cali Cartel boss Gilberto Rodríguez Orejuela dies in U.S prison

Cali cartel boss Gilberto Rodríguez/Policia Nacional

Cali Cartel boss Gilberto Rodríguez Orejuela has died, age 83, as an inmate of the Federal Correctional Institution in Butner, North Carolina.

Gilberto Rodríguez Orejuela, co-partner in crime with his younger brother Miguel, oversaw a cocaine empire that extended from their home city of Cali, in southwest Colombia, to the streets of Chicago, Miami and New York. As the bosses of a drugs syndicate dubbed “Cali Inc.,” the white collar Rodríguez brothers managed both legitimate businesses from a pharmaceutical retail outlet (Drogas La Rebaja), and stakeholders in the local football team America de Cali, to their illegal enterprise responsible for up to 80% of all cocaine shipments to the U.S during the mid 1990s.

Living in the gated community of Ciudad Jardín, in the south of Cali, and preferred clients of the city’s Intercontinental Hotel for birthday and anniversary celebrations, Gilberto worked under the nickname “The Chess Player” given his skill at expanding the cartel’s financial operations to neighboring countries, as well as establishing off-shore money laundering hubs, guarded by clever lawyers and skewed accountants.

With large swathes of the Colombian economy under their control, the Cali Cartel bankrolled the country’s courts for lax plea bargain arrangements, and legalization of drug consumption. But the mobsters’ most infamous payment to expand their sphere of political influence involved a “donation” of US$3.6 million to the campaign of Ernesto Samper.

The day after Conservative leader Andrés Pastrana lost the race to the Liberal Party’s official candidate, he handed out copies of an audiotape that allegedly contained a conversation between the Rodríguez brothers and Alberto Giraldo, a journalist acting as a go-between. The trio were heard discussing arrangements to “send around some money” to Samper’s ostentatious campaign manager Santiago Medina.

As two more tapes surfaced in the following days, the scandal cast suspicion not only on Samper, but the corruptible nature of Colombia’s political elites and high-ranking members of the security forces, including national police chief Octavio Vargas. Samper, who promised to invest in large-scale infrastructure, schools and education, claimed that any dirty deal with the Cali Cartel was done “behind his back.”

In an interview days before his inauguration, Samper responded to accusations he had contact with the cocaine cartels, stating: “The only contact I have with drug traffickers is the four slugs I’ve still got in my gut from the time they tried to kill me.” Samper, a lawyer and an economist, was severely wounded by 11 bullets during the assassination of Patriotic Union leader José Antequera.

Even though Samper denied allegations of illegal campaign financing from an organization that repatriated an estimated US$2.1 billion in drug money during the height of their criminal operations – much of it destined to Cali – the cartel’s genteel modus operandi was in sharp contrast to the violent Medellín Cartel; even though, both organizations worked alongside low-level narcotraficantes, among them José Santacruz Londoño, Grajales family and Ochoa clan, in buffer zones once controlled by Pablo Escobar.

After the U.S revoked President Samper’s visa during the midterm of an embattled presidency, and one tarnished by the criminal investigation known as the Proceso 8.000, in 1995, Samper moved-in to capture the “gentleman” drug-lords. Samper, under immense pressure to give the war on drugs higher priority and U.S skepticism of his drug-fighting credentials, began a crackdown on the Cali Cartel’s free-reign on money laundering and financing of banks, casinos, country clubs, real estate, even the Miss Colombia beauty pageant.

One of the longest investigations in DEA history led to the arrest of Gilberto, brother Miguel and associates Hermer Herrera and Santacruz Londono. The operation involved female undercover agents disguised as joggers who located “The Chess Player” following “a scent of cheap cologne.”

Sentenced to serve 15 years in a Colombian prison, and from where they continued to flood U.S and European markets with cocaine, in 2004, under order of President Álvaro Uribe, Gilberto Rodríguez – then 65 years of age – was extradited to the U.S to face drug trafficking charges in a Florida court. Miguel, age 60, was extradited a year later.

In 2006, the Rodríguez brothers pleaded guilty for importing more than 200 tons of cocaine, and were each served by Judge Federico Moreno of the U.S. District Court for the Southern District of Florida a prison sentence of 30 years.

“As drug traffickers and kingpins around the world now know, they are not beyond the reach of justice in the United States – the Cali Cartel has been dismantled and the brothers now face years in American prisons,” remarked former Attorney General Alberto Gonzales with the verdict.

“These brothers rank as arguably the highest-level trafficking figures to ever occupy U.S. jail cells. Their guilty pleas mark the culmination of 15 years of investigation by ICE agents, DEA agents and Colombian authorities,” said Julie Myers, then Assistant Secretary for U.S. Immigration and Customs Enforcement.

In 2020, Gilberto Rodríguez appealed the court for compassionate release citing life-threatening health problems with the coronavirus pandemic. The prisoner suffered from colon cancer, prostate cancer, high blood pressure, skin cancer, gout, chronic anxiety and depression. According to an AP report, “the documents paint a picture of a frail old man who often must use a walker and frequently visits the infirmary at his prison in Butner, North Carolina.”

Judge Moreno ruled against early release, stating that “Rodriguez Orejuela’s medical condition, while far from perfect, is also far from extraordinary and compelling.”