One of the escapees is accused of torturing and mutilating the owner of a marijuana dispensary. Another was awaiting trial for a gang-related murder. The third was charged with shooting into a house full of people.
Now the three, who made a daring escape from the Orange County Men's Jail on Friday, are the focus of a massive manhunt across Southern California involving hundreds of police officers and the FBI.
"We absolutely need the public's help," Lt. Jeff Hallock of the Orange County Sheriff's Department said Monday. "These three are extremely dangerous felons."
Initial investigation found no assistance from anyone inside the jail and no guards have been suspended in connection with the first successful breakout from the jail in downtown Santa Ana in nearly 30 years, sheriff's Lt. Dave Sawyer said.
A $50,000 reward has been offered for information leading to the recapture of the three escapees — Hossein Nayeri, 37, Jonathan Tieu, 20, and Bac Duong, 43.
Tieu and Duong are both members of local Vietnamese street gangs, Sawyer said, and the department made a direct appeal to that community for help in locating them.
Nayeri is the most notorious of the three. He was being held of two counts of kidnapping, extortion, aggravated mayhem, torture and other charges stemming from a stomach-churning episode that could have been an episode from "Breaking Bad."
Prosecutors said Nayeri and two other men used a blowtorch to torture a licensed pot dealer in the mistaken belief he had money buried in the desert. They then sliced off his penis and poured bleach on him before dumping him and his girlfriend by the side of a road.
Nayeri tried to flee to Iran but was caught by the FBI in Prague. He had been held at the jail since September 2014.
Tieu is a gang member who had been in the jail since October 2013 and charged with murder, attempted murder and street terrorism, officials said.
Duong, who is also a gang member, had been at the jail for little over a month and was charged with attempted murder, burglary, three firearms violations and other charges.
The three escapees were being held in a large dormitory-style cell with 65 other prisoners when they cut through the steel grate behind their bunk beads some time after the Friday morning head count and slithered through a plumbing tunnel to reach the roof, Hallock said.
Along the way, they had cut through several half-inch bars and plumbing ducts, he said.
Hallock said that once on the roof they used a "makeshift rope" to rappel down several stories to the ground. He said the guards didn't notice they were gone until they did the 9 p.m. Friday head count.
Investigators don't know where the escapees got the tools, whether they shed their orange prison uniforms before the left the hulking jail complex, or if there was a getaway driver waiting outside for them. But they suspect a fight in the dormitory around 8 p.m. Friday was staged to give the escapees more time to get away.
Clearly, said Hallock, it was a "very well thought-out" escape plan.
This article originally appeared on NBCNews.com.