The Treasury Department on Thursday effectively relegated the Cali cartel to the dustbin of history, removing 308 individuals and entities associated with the infamous Colombian drug-trafficking organization from a U.S. sanctions list.

The removal of the 78 individuals and 230 entities, mostly in Colombia, is the largest delisting in the Treasury’s history.

The cartel originated in the city of Cali in 1977 and gained notoriety alongside the hyper-violent Medellin cartel helmed by Pablo Escobar in the 1980s. While the Medellin cartel adopted terror as its calling card, its Cali counterpart relied more on intimidation than violence.

In 2006, the leaders of the Cali cartel, brothers Miguel and Gilberto Rodriguez Orejuela, were captured and extradited to the United States after more than a decade-long campaign to disrupt and seize their assets. The brothers subsequently pleaded guilty to numerous drug-trafficking charges across multiple states and were sentenced to 30 years in prison. They forfeited $2.1 billion in assets worldwide.

“Today’s action demonstrates the successful use of targeted sanctions, which have destroyed the Rodriguez Orejuela brothers’ business empire,” Adam J. Szubin, director of Treasury’s Office of Foreign Assets Control, said in a statement.

In conjunction with the brothers’ 2006 guilty plea, a number of their family members who were then under Treasury sanctions were forced into an agreement with the Justice Department and Treasury to end ties with the narcotics-trafficking business, forfeit property and proceeds to the Colombian government, and identify any other family members in possession of Cali cartel assets.

The family members who complied have been removed from the sanctions list, while those who attempted to conceal cartel assets were subsequently prosecuted by the Colombian government, the Treasury said.

“The sustained economic pressure on the Cali Cartel, at its height the most powerful drug trafficking organization in the world, stemmed from close coordination between multiple U.S. law enforcement agencies and our Colombian counterparts,” Szubin said. “We continue to support Colombian authorities as they prepare to finalize the forfeiture of the Rodriguez Orejuela brothers’ assets.”

Currently, the only cartel members still sanctioned by the Treasury are the two brothers themselves.