José Figueroa Agosto

In 1999, Figueroa Agosto escaped from prison in Puerto Rico, where he was serving a 209-year sentence for murder and illegal weapon possession. He originally went to prison on murder charges in Puerto Rico, but escaped and fled to the Dominican Republic, where he managed to obtain several alternate identities and continued drug trafficking for another 10 years. While in the Dominican Republic he was arrested in a minor stint as one of his alternate identities and then released for an unknown reason (his alter ego was not yet known to the authorities). Following a lead in late 2009, one of his many apartments was raided, and police found $4 million in cash and $1 million in watches. A car chase followed, but he managed to elude the police by fleeing his vehicle and hiding in a sewer. Eventually, he managed to return to Puerto Rico, allegedly by paying 1 million dollars to unnamed high-ranking military personnel. He was able to hide in San Juan, Puerto Rico for 10 months, until July 2010, when DEA, FBI, US Marshals and Puerto Rican police arrested him in Santurce, a district of the capital city of San Juan, as he tried to escape from officers conducting surveillance. Figueroa Agosto was the most wanted fugitive by the Puerto Rican and Dominican Republic authorities.

In 2017, authorities believed that with the Caribbean's biggest reputed drug lord back behind bars, law enforcement authorities in the region should be on alert for potential bloody feuds among rivals and lieutenants trying to take his place. Capture of Jose Figueroa Agosto in Puerto Rico's capital after a decade-long hunt was a big break, but it also meant that members of his violent group would try to gain control of his share of the illegal trade.[5]

Authorities say Figueroa Agosto, worked as a drug-boat driver until 1993, when he carried out a hit on a truck driver who allegedly stole a shipment of Colombian cocaine. Puerto Rican courts convicted him of the murder and sentenced him to 209 years in prison. But in 1999, he walked out of the prison's front gates after presenting the guards with a falsified release order. He was on the run for the next 11 years, leading his criminal organization while living what U.S. Marshals described as a luxury lifestyle in both the Dominican Republic and Puerto Rico. He allegedly bought homes and cars under false identities. At one point, Figueroa Agosto — or a man claiming to be him — called a popular Dominican morning radio show and offered an $800,000 reward for the murder of either of the country's two top police officials.

At the time of his capture, he was on the lam after being convicted in Puerto Rico for a 1993 murder. His capture was a law enforcement priority in the Dominican Republic and the United States and Dominican President Leonel Fernández and United States Attorney General Eric Holder were personally involved in the decision-making process leading to his capture. Dominican Police Chief Rafael Guillermo Guzmán had called Figueroa Agosto's capture "the Dominican state's biggest challenge".

At the ending of the 10-year manhunt, like fellow smuggler Christopher "Dudus" Coke in Jamaica, Figueroa Agosto was arrested wearing a wig after having had various plastic surgeries. He was wanted for allegedly moving cocaine through the Dominican Republic and Puerto Rico with fellow co-worker, Angelo Millones, into the United States. Figueroa Agosto was also charged by U.S. authorities with passport fraud and unlawful flight to avoid prosecution. There were rumors that Figueroa Agosto would be on the streets soon; if there was no proof by the federal agents, they could not put him behind bars.

His romantic companion had been captured months before he was and reportedly was cooperating with authorities[6] after appearing in pornographic videos protagonized by both of them.[7]

Dominican authorities have sought Figueroa Agosto for multiple violations including kidnapping, money laundering, drug trafficking and murder. He was also linked to criminal activity in Colombia and Venezuela, according to the DEA, but they have not charged him for trafficking.

He pleaded guilty to drug trafficking charges in 2012, and in 2017 he was sentenced to 30 years in prison.[8] He was released in 2020 after serving 10 years in prison.[9][10]

In 2010, a sex tape of Figueroa Agosto proved to be a popular sell among porn DVD vendors in Puerto Rico and Dominican Republic.[3]