Updated

The U.S. Treasury Department blacklisted 20 entities and one person linked to a Mexican drug lord who was recently released on a technicality in the torture-murder of a Drug Enforcement Administration agent.

Rafael Caro Quintero has spent the last 28 years of a 40-year sentence locked up in a Mexican prison for the killing of Enrique “Kiki” Camarena.

Quintero was originally sentenced to spend 40 years behind bars, but was released on Aug. 9 with 12 years still left on his sentence.

Security guards were assigned to follow Quintero after his release, but the former cartel boss was able to quickly shake them, a source familiar with the events told FoxNews.com.

The details behind the unexpected release of Quintero have threatened an already fragile relationship between the U.S. and Mexico.

Authorities say Camarena was tortured before his execution -- viciously beaten, with his tormenters reportedly using a screwdriver to drill a hole in his head; a doctor was employed to keep him alive and conscious during the interrogation. A detailed 1985 Miami Herald report on the kidnapping said Camarena suffered a broken jaw, a broken nose, broken cheekbones and a crushed windpipe.

Camarena's body was later discovered, along with that of his Mexican pilot, on a ranch outside Guadalajara.

Quintero’s criminal career began in the late 1970s, when he founded one of the most notorious drug cartels in the country. During his illegal ventures, authorities say he “amassed an illicit fortune.”

While in prison, officials say Quintero kept up alliances with Mexican drug trafficking organizations and used a network of family members, front men and friends to invest the money he made illegally in legitimate companies and real estate investment deals.

U.S. authorities want to cut off the cash to Quintero and his associates. They had added him, 20 businesses he is associated with as well as Juan Carlos Soto Ruiz, a Guadalajaran native who manages six of the companies, to the list.

“Caro Quintero and his organizations can no longer hide behind front companies with their drug trafficking profits,” DEA spokeswoman Michele Leonhart said in a written statement. “These illegal enterprises fuel the drug trade and its violence and corruption. DEA and our partners at Treasury and elsewhere in government will pursue any and all means available to ensure that Caro Quintero is brought to justice and his criminal network is destroyed.”

Since 2000, the U.S. has identified 103 drug dealers and 1,300 businesses and individuals as part of the Kingpin Act.

The law prohibits companies and people in the U.S. from conducting any type of financial or commercial transaction with those on the list. Civil penalties can hit more than $1 million per violation. Criminal penalties for corporate officers caught breaking the law can result in fines up to $5 million and 30 years in prison.

In September, Vice President Joe Biden traveled to Mexico to meet with President Enrique Peña Nieto as a way to strengthen the economic relationship between the neighboring nations.

There was no mention in their public press conference of Quintero’s release.