[1] While working his way up in the pharmacy business, Rodríguez Orejuela began his criminal career, engaging in kidnapping and then, the drug trade.

[1] During the 1970s, Rodríguez Orejuela and his brother Miguel helped to organize, along with José Santacruz Londoño and Hélmer Herrera, a loose consortium of drug trafficking gangs that came to be known as the Cali Cartel.

Gilberto was the strategic planner and visionary, nickname "The Chess Player" for his calculated approach; Miguel oversaw day-to-day operations.

The cartel began to work with traffickers in Galicia, and established strategic alliances with the powerful Camorra, which would be in charge of the distribution of Cali cocaine throughout Europe.

[citation needed] On 9 June 1995, Rodríguez Orejuela was arrested by the Colombian National Police (PNC) during a house raid in Cali.

[6] He was sentenced to 15 years in prison but was freed in October 2002, by a controversial judicial order that cited good behavior and participation in work-study programs, issued by deputy judge Pedro José Suárez.

[7][8][9] In March 2003, Rodríguez Orejuela was rearrested by Colombian authorities in Cali, on new charges stemming from running the cartel from prison.

[citation needed] On 26 September 2006, both Gilberto and Miguel were sentenced to 30 years in prison, after pleading guilty to charges of conspiring to import cocaine to the US.

[15][16] Specifically, the court found that the family had used their legitimate businesses (including the pharmacy chain Drogas La Rebaja) to launder billions of pesos.

[citation needed] At the time of his death, Gilberto Rodríguez Orejuela was serving a 30-year sentence at the Federal Correctional Institution, Butner, a medium-security facility in North Carolina.

[1] On 6 February 2020, Rodríguez Orejuela submitted an application to a Miami federal judge seeking compassionate early release pursuant to the First Step Act.

The judge stated that "the court is totally unwilling to undermine and undo such public respect for the law, as well as the gravity of the offenses committed" and that while Rodríguez Orejuela has endured a litany of chronic illnesses including cancer, his criminal record was so repugnant that there is no way he could effectively cut his sentence in half.