MIAMI (AP) — Gilberto Rodríguez Orejuela, an elderly leader of the former Cali cartel that smuggled vast amounts of cocaine from Colombia to the United States in the 1980s and 1990s, has died in a U.S. prison, his lawyer said Wednesday.

In 2020, a judge had denied Rodríguez Orejuela, who was in his 80s, early release on compassionate grounds from a prison in Butner, North Carolina. His attorney, David O. Markus, had said at the time that the former drug kingpin was suffering a range of health problems.

“We were very sad to learn about his passing last night. Our thoughts and prayers are with his family at this time,” Markus said Wednesday.

“God has a new chess partner,” the lawyer said, referring to Rodríguez Orejuela’s reputation for outsmarting his enemies and rivals, for which he earned the nickname “the chess player.”

Rodríguez Orejuela and his brother, Miguel, built a huge criminal enterprise that succeeded the Medellin cartel once run by drug lord Pablo Escobar. Both operations used violence and killings extensively for intimidation and enforcement.

The Rodríguez Orejuela brothers were captured in 1995 and imprisoned in Colombia. At that point, Colombian law prohibited the extradition of its nationals. But under pressure from the U.S, Colombia lifted that ban in 1997.

The brothers were found to have been continuing to traffic from prison and criminal charges were filed in Miami and New York. In 2004, Gilberto was extradited; Miguel was extradited the next year.

Under a 2006 plea deal that the brothers reached with federal prosecutors in Miami, more than two dozen family members were removed from a U.S. Treasury Department list designating them as part of the Cali cartel. That spared some of them from prosecution for obstruction of justice or money laundering and also allowed legitimate family businesses in Colombia to continue operating.

Gilberto Rodriguez Orejuela’s prison release date had been scheduled for Feb. 9 2030. His younger brother, is serving his sentence at a Pennsylvania prison.

Perhaps the biggest legacy of the Rodríguez Orejuela brothers was their ability to quietly corrupt Colombian politics, delivering shoeboxes of cash to Ernesto Samper’s campaign prior to his 1994 election as president and buying off much of Congress. While painted in the popular press as less violent than Pablo Escobar and the Medellin cartel, the Rodríguez Orejuelas brothers were later accused of paying off journalists to suppress news of Cali cartel-related killings.

New ranks of narcos quickly replaced the Cali cartel leaders after their arrest and extradition. Many of those successors became leaders of far-right military bands that the U.S. placed on its international terror group list in 2001.

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Associated Press journalist Frank Bajak contributed from Boston.

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