HomeColombiaGilberto Rodríguez Orejuela, alias 'The Chess Player'

Gilberto Rodríguez Orejuela, alias 'The Chess Player'


For more than two decades, Colombian kingpin, Gilberto Rodríguez Orejuela, alias “El Ajedrecista,” meaning “The Chess Player,” was one of the leaders and founders of the now-defunct Cali Cartel, a confederation of 15 criminal groups dedicated to moving cocaine to the United States and Europe. 

Along with his younger brother, Miguel Rodríguez Orejuela, Gilberto came to control 80 percent of the cocaine market in the United States. But despite becoming one of the United States’ most wanted drug traffickers by 1989, Orejuela still managed to pose as a businessman in Colombia, allowing him to escape the clutches of justice.

The end of Orejuela’s criminal emporium began in 1995 when he was arrested at one of his ostentatious properties in the city of Cali, the capital of Valle del Cauca department, located in southwestern Colombia. Orejuela was sentenced to 30 years in a US prison. From 2006 until his death on May 31, 2022, Orejuela served his sentence at the Butner federal prison in North Carolina.


Gilberto Rodríguez Orejuela was born on January 30, 1939, in the Mariquita municipality, in the Tolima department. The infamous Colombian drug trafficker received his first salary by transporting drugs, but for licit use. When Gilberto was 13 years old, he worked as a messenger for the drugstore La Perla, cycling around his hometown to bring medicine to an elderly woman.

Then his parents, a painter and a housewife decided to move to the city of Cali. There he grew up with his younger brother Miguel, who would later become his business partner. 

While studying at the San Luis Gonzaga school in the capital of Valle del Cauca, Gilberto also worked as a messenger for a pharmacy. There, he not only distributed drugs but also cheated on drug prices and the medical authorizations needed to sell them.

Towards the seventies, El Ajedrecista took important steps into the illegal sphere, joining a group of merchants who would later form the infamous Cali Cartel, to smuggle contraband fabric and whiskey. He also got involved in the criminal gang "Los Chemas," which was accused of kidnapping two foreigners from a diplomatic family in Cali.

By 1975, Gilberto Rodríguez Orejuela already exported large quantities of cocaine, camouflaged on thick wooden planks shipped in licit shipments from the port of Buenaventura, on Colombia’s Pacific Coast, to various warehouses and fictitious companies in the United States. In 1976, El Ajedrecista was linked to drug trafficking activities, after 290 kilos of coca paste were seized leaving Peru for Colombia.

Two years later, authorities discovered a cocaine distribution network in Queens, New York, which was allegedly controlled by Rodríguez Orejuela.

During the 1970s, the Colombian capo not only positioned himself in the world of drug trafficking but also expanded his licit emporium. Along with Miguel, Gilberto penetrated the legal world of capital, as a wealthy investor in different firms, banks, and companies, such as Laboratorios Kressfor, Drogas La Rebaja, Grupo Radial Colombiano, and Corporación Financiera de Boyacá, Chrysler and the First Interamericas Bank de Panamá. 

By the mid-1980s, under the leadership of the Rodríguez Orejuela brothers, the Cali Cartel had already managed to consolidate itself as one of the main drug trafficking organizations in the hemisphere. By that time, they had their own routes and markets, and the US and European authorities had already identified signs of their activity; Gilberto’s arrest, while with drug trafficker Jorge Luis Ochoa in Madrid, Spain at the end of 1984, was proof of this. After being locked up for more than 12 months, the government of Felipe González authorized his extradition to Colombia, and they were handed over to the authorities in 1986.

Once in Colombian territory, El Ajedrecista was transferred to the Bellavista prison in Cali, where he remained for 13 months. Despite the 11th criminal judge of the Cali Circuit, Tobias Iván Posso, opening a process against Gilberto for drug trafficking, Gilberto was acquitted due to a lack of evidence in 1988 and he went back to the criminal underground.

While Gilberto Rodríguez Orejuela managed to resolve his judicial processes in his favor, his days of freedom were numbered. In 1995, the US Treasury Department published a list of companies whose ownership was awarded to the Rodríguez Orejuela brothers and at least a hundred were linked to the druglords. 

Additionally, that same year, the Search Bloc, an elite police unit formed in 1989, captured the Colombian drug trafficker in a luxurious home in Cali’s Santa Mónica neighborhood. Rodríguez Orejuela was immediately transferred to Bogotá, where he was initially sentenced to 12 years in prison, but his sentence was reduced to seven for confessing to some crimes and for good conduct.

El Ajedrecista regained his freedom, but his luck changed in 2004 when the Attorney General's Office arrested him for sending 150 kilos of cocaine to the United States in 1990. The US government solicited the extradition of the Colombian kingpin, and in 2006 Gilberto was sentenced to 30 years in prison for conspiring to import cocaine into the United States and launder drug money. Gilberto Rodríguez Orejuela was held at the Butner federal prison, until his death, of lymphoma of the brain, on May 31, 2022.

Criminal Activities

Gilberto Rodríguez Orejuela and his brother Miguel founded the Cali Cartel, one of the most important drug trafficking organizations of the eighties and nineties. Under the brothers’ leadership, Helmer Herrera and José Santacruz Londoño, the criminal group imported at least 200 tons of cocaine to the United States, which corresponded to 80 percent of the drugs circulating in the United States. The sophisticated organization controlled all phases of the cocaine trafficking production chain, including the production, transportation, and distribution, as well as money laundering.

US authorities determined that between 1990 and 1993, the Rodríguez Orejuela brothers hid at least 137 tons of cocaine in shipments of concrete poles, frozen vegetables, coffee, and ceramic tiles. The shipments moved in container ships from Colombia to South Florida, with stops in Venezuela, Panama, and Guatemala, and represented at least $1.3 billion in profits for the Cartel de Cali. Unlike other drug lords at the time, Gilberto tried to keep a low profile, mobilizing in a modest car and surrounded by a small security convoy that included women.

His arrest in Spain in 1984, revealed that he also moved in European territory, where, according to Blu Radio, he posed as a businessman named Gilberto González Linares. El Ajedrecista also traveled through Latin America for leisure. In an interview with the journalist Julio Sánchez Cristo, Gilberto revealed that he frequently traveled to see his soccer team, América de Cali, play. For example, in 1984, before being detained in Spain, he flew to the city of Rio de Janeiro to watch the match between Flamengo and the América de Cali. 

Allies and Enemies

Under the leadership of the Rodríguez Orejuela brothers, Herrera and Santacruz, the Cali Cartel formed alliances with national and international political figures and criminal organizations. 

However, by 1988, El Ajedrecista's actions and wealth had also earned him some enemies, resulting in a relentless war with the Medellín Cartel, led by Pablo Escobar.

One of the Cali Cartel’s allies in this fight was the group Persecuted by Pablo Escoba (Perseguidos por Pablo Escobar - Pepes), which represented the criminal interests of those that had once been members of the Medellín Cartel, and who were now declaring war on their top leader, Escobar. By 1992, the Cali Cartel had contributed at least $30 million to the Pepes to fight the dispute with the Antioquia kingpin.

Gilberto also formed alliances with European criminal organizations. In the mid-1980s, he established a system of cocaine transport and distribution in Europe through La Camorra, a mafia clan in Italy.

Members of Colombia's political elite were also among the Cali Cartel’s allies. 

In 1995, president-elect Ernesto Samper Pizano, was accused by his opponent, Andres Pastrana Arango, of having received at least $3.7 million from the Cali Cartel to finance his campaign. Evidence of this included cassettes in which Miguel and Gilberto Rodríguez Orejuela were heard admitting that they had delivered money for Samper's presidential campaign. However, the investigations advanced by judicial authorities at that time determined that there was not enough evidence of drug money sponsoring Samper's presidential campaign and that he had knowledge of this fact.

One of Gilberto Rodríguez Orejuela’s long-time enemies was Pablo Escobar. Although El Ajedrecista’s drug trafficking organization had cooperated with the Medellin Cartel to stabilize the drug market and divide territory in the United States for the distribution of cocaine in the early 1980s, by the end of the decade both cartels were already waging a brutal territorial struggle in Colombia. In an interview with journalist Sánchez Cristo, Gilberto said Escobar declared war in December 1987, after the Cali Cartel leader refused to terrorize the country to avoid extradition.

“So Gilberto, that means you are not my friend, and since you are not my friend, then you are my enemy, and I will treat you as an enemy from now on,” Escobar told El Ajedrecista, according to the interview with Sánchez Cristo.

Legacy and Influence

Gilberto Rodríguez Orejuela’s arrest not only represented the decline of the Cali Cartel, but also the end of the first generation of Colombian drug trafficking, led by Cali and the Medellín Cartel. However, El Ajedrecista’s criminal career also left behind a legacy, one that illustrated how the infiltrating branches of public power could prove more strategic to drug traffickers than waging a war against the State.

The structure that El Ajedrecista established within drug trafficking organizations of the late twentieth century has disappeared, and with it, the cartels' ability to control all the links of the drug trafficking chain. Hierarchical organizations, vertically integrated and with a clearly defined command structure, have become discrete, globalized networks, made up of different cells and ready to cooperate rather than enter a dispute.

Gilberto Rodríguez Orejuela understood that, rather than starting a war with the Colombian state, at that time focused on persecuting Pablo Escobar and endorsing his extradition, he should instead infiltrate the ttate. This is how the leader of the Cali Cartel sought to guarantee non-action by the authorities against him through the acceptance of the ruling class and access to branches of power. “We have to have a president on our side,” El Ajedrecista said when explaining his strategy to continue his drug trafficking operations.

Like the drug lords that entered the country in the early 21st century, the Rodriguez Orejuela brothers did not try to enter politics but rather sought to buy their support. An example of this was the scandal that erupted involving former President Ernesto Samper, who allegedly received money from the Cali Cartel to finance his campaign.

The sophisticated intelligence system employed by the Cali Cartel allowed the organization to grow stronger as state forces focused on capturing Pablo Escobar. Before being extradited to the United States, Rodríguez Orejuela revealed that he had intercepted Escobar's phones to secure his capture. “We tapped his phones, we recorded him. We have more than 500 cassettes of Pablo Escobar,” he said. That collaborative relationship with Colombian authorities opened a window of opportunity for El Ajedrecista to expand his operations as his biggest rival’s empire collapsed.

Unlike the narcos of the time, Gilberto Rodríguez Orejuela tried to go unnoticed with his investments. The leader of the Cali Cartel penetrated the legal economy in various sectors through front companies and international banking. Instead of acquiring ostentatious goods, Gilberto’s financial decisions allowed El Ajedrecista to enjoy his reputation as an entrepreneur, rather than as a narco-trafficker, and enabled him to move more easily around Colombian territory.

This modus operandi is similar to that of the invisible drug traffickers, which became common after the fall of the Cali Cartel. This new generation of criminals has understood that luxuries and eccentricities can become counterproductive, drawing the attention of the media and the authorities. For this reason, they choose to portray themselves as businessmen and entrepreneurs.

Such is the case of Guillermo León Acevedo Giraldo, alias “Memo Fantasma,” an elusive drug trafficker and former paramilitary commander who now describes himself as a businessman and real estate investor. His low profile and entrepreneurial image allowed him to stay off the authorities’ radar for more than two decades and even rub elbows with the elites of Colombia's exclusive economic and political sectors.

share icon icon icon

Was this content helpful?

We want to sustain Latin America’s largest organized crime database, but in order to do so, we need resources.


What are your thoughts? Click here to send InSight Crime your comments.

We encourage readers to copy and distribute our work for non-commercial purposes, with attribution to InSight Crime in the byline and links to the original at both the top and bottom of the article. Check the Creative Commons website for more details of how to share our work, and please send us an email if you use an article.

Was this content helpful?

We want to sustain Latin America’s largest organized crime database, but in order to do so, we need resources.


Related Content

COLOMBIA / 16 JUN 2022

Jobanis de Jesús Ávila Villadiego, alias "Chiquito Malo," is the current commander of the AGC, succeeding Otoniel.

About InSight Crime


InSight Crime Contributes Expertise Across the Board 

22 SEP 2023

This week InSight Crime investigators Sara García and María Fernanda Ramírez led a discussion of the challenges posed by Colombian President Gustavo Petro’s “Total Peace” plan within urban contexts. The…


InSight Crime Cited in New Colombia Drug Policy Plan

15 SEP 2023

InSight Crime’s work on emerging coca cultivation in Honduras, Guatemala, and Venezuela was cited in the Colombian government’s…


InSight Crime Discusses Honduran Women's Prison Investigation

8 SEP 2023

Investigators Victoria Dittmar and María Fernanda Ramírez discussed InSight Crime’s recent investigation of a massacre in Honduras’ only women’s prison in a Twitter Spaces event on…


Human Trafficking Investigation Published in Leading Mexican Newspaper

1 SEP 2023

Leading Mexican media outlet El Universal featured our most recent investigation, “The Geography of Human Trafficking on the US-Mexico Border,” on the front page of its August 30…


InSight Crime's Coverage of Ecuador Leads International Debate

25 AUG 2023

This week, Jeremy McDermott, co-director of InSight Crime, was interviewed by La Sexta, a Spanish television channel, about the situation of extreme violence and insecurity in Ecuador…