Authorities escort Joaquín "El Chapo" Guzman from a plane to a waiting caravan of SUVs at Long Island MacArthur Airport in New York on Jan. 19. (U.S. Law Enforcement via AP)

A Mexican cartel leader once allied with Joaquín “El Chapo” Guzmán, the world’s most notorious drug lord, was sentenced Wednesday in Washington to life in prison and a $529 million forfeiture.

Alfredo “El Mochomo” Beltrán-Leyva and his brothers once ran an organization that served as the armed wing of Guzmán’s Sinaloa cartel, Mexico’s most powerful drug syndicate, court files show. But El Mochomo’s capture by Mexican special forces in 2008 — which Mexican federal officials said his siblings blamed on Guzmán — launched a string of shadowy betrayals between the groups and detonated a bloody drug war with effects that haunt Mexico nearly a decade later.

[Mexican agents arrest brother of Beltrán Leyva, drug lord killed in raid]

Now, U.S. prosecutors have closed in on both kingpins. The prosecution of Beltrán-Leyva, who pleaded guilty last year, offers a tantalizing glimpse of the U.S. government’s long pursuit of Guzmán, including a shared cast of cooperating witnesses and a trail of escalating financial penalties including plea deals to hand over billions in illegal gains.

The half-billion dollar forfeiture order by U.S. District Judge Richard J. Leon of the District comes after judges in Washington have entered judgments of at least $10 billion since 2013 against Gulf cartel members, the largest criminal financial penalties in a U.S. drug prosecution.

Mexican federal police officers escort Alfredo Beltrán-Leyva, known as "El Mochomo, upon his arrival at Mexico City's airport on Jan. 21, 2008. (Eduardo Verdugo/AP)

Prosecutors had asked for a $10 billion order Wednesday — their estimate of the Beltrán-Leyva organization’s gross receipts from 2000 to 2012 derived from the retail price of drugs seized.

U.S. authorities are asking for a $14 billion order against El Chapo, who was extradited to the United States in January and awaits federal trial in Brooklyn.

[After drug lord’s arrest, Mexico braces for fallout]

Beltrán-Leyva was one of the “Goliaths” of Mexican drug traffickers whose savage tactics spread fear across the region, U.S. justice and homeland security officials said. His case is “one of the most significant major Mexican cartel convictions ever in our country’s long-running battle against these criminal organizations,” Justice Department spokesman Peter Carr said.

How much money the U.S. government actually recovers from Beltrán-Leyva remains to be seen. The amount depends on identifying as-yet-unknown assets to be seized that then also would be shared with victims and law enforcement, particularly in this case “our Mexican law enforcement counterparts, whose efforts were invaluable to Mr. Leyva’s extradition and our successful prosecution of him,” Carr said.

El Mochomo, or “The Desert Ant,” 47, was the youngest of the five Beltrán-Leyva brothers, each now killed or in custody, and was so close to Guzmán that he married his cousin. But Mexican news media reported that Guzmán sold out the youngest Beltrán-Leyva to obtain the release of his own son, said Chivis Martinez of Borderland Beat, an English-language blog that closely covers cartel cases.

Beltrán-Leyva pleaded guilty on the eve of trial in Washington in February 2016 without a cooperation deal — a rare “bare plea” by a top cartel target — with federal prosecutors. He admitted conspiring to distribute multi-ton shipments of South American cocaine for importation in the United States from 2000 to 2008, and controlling a key trafficking route through Culiacán, Sinaloa, his plea stated. Beltrán-Leyva was indicted in the United States in 2012, extradited in November 2014 and pleaded guilty on Feb. 23, 2016.

“I helped my brother Arturo to sell cocaine in Culiacán knowing that it was coming to the United States,” Beltrán-Leyva said in court Wednesday, through an translator. But he maintained he had nothing to do with shipments from Colombia, “never sent one kilo” himself to the United States, and that government cooperators testifying against him worked for Arturo, not him, a stance that has led some in Mexico to call him the “reluctant narco.”

“I would like to apologize, your honor, and ask forgiveness for the behavior that has gotten me here, and I apologize to God, to the highest authorities, and to my children,” said the clean-shaven defendant, wearing black eyeglasses and a tan prison jumpsuit.

The “BLO” was known for its violence and corrupting reach, said Steven S. Dudley, co-director of Insight Crime, a think tank that studies organized crime in the Americas.

Beltrán-Leyva oversaw dozens of subordinates — including sicario, or hit men — responsible for countless “murders, kidnappings, tortures and violent collections of drug debts,” U.S. officials said in court filings.

A witness who cooperated with U.S. investigators asserted that El Mochomo controlled two groups of more than 100 hit men armed with assault rifles, bazookas and .50-caliber weapons for his organization’s protection, and returned from a meeting with El Chapo wearing a tactical vest with grenades, according to an FBI summary of testimony by the witness, Sergio Villareal-Barragán a former BLO member known as “La Grande.”

Beltrán-Leyva’s attorney, A. Eduardo Balarezo, in arguing unsuccessfully for a 25-year sentence, called the prosecution “a classic example of the reliance the government places on cooperators” who “have often done far worse than the people they snitch on.”

Villareal-Barragán was an enforcer and former federal police officer charged with many killings who is cooperating under U.S. indictment. Another promised government trial witness, Edgar “La Barbie” Valdez Villareal, who pleaded guilty in a deal with U.S. prosecutors in January 2016, led a BLO assassination team known for its brutality that was responsible for a majority of BLO’s killings, the U.S. State Department said before his capture, killings that included videotaped executions, beheadings and grisly displays of corpses.

Leon rejected those claims, saying evidence had shown Beltrán-Leyva “was an organizer and a leader of one of the largest drug trafficking organizations in the world, a rival to the Sinaloa Cartel and El Chapo Guzman,” which used violence and deployed bribes across society.

Citing a recent D.C. circuit appeals court ruling, the judge said he was required to limit a forfeiture order to a “very conservative” dollar amount, calculated based on 28 tons of cocaine shipped that an eyewitness directly linked to Beltrán-Leyva.

Michael S. Vigil, a 31-year DEA special agent who worked undercover, headed its Caribbean field division and office of international operations before retiring in 2004, said that although prosecutors and Beltrán-Leyva’s attorneys at one point explored a plea deal in early 2015, he saw no sign that he provided assistance.

“There is no love lost between Alfredo Beltrán-Leyva and El Chapo Guzmán. But whether he cooperates against El Chapo Guzmán, that’s a different story,” said Vigil, now an author and consultant.

Nevertheless, the two men’s fates appear deeply entwined in cases in U.S. courts.

After Alfredo’s capture, Mexican federal officials and news reports said the Beltrán-Leyva blamed Guzmán for tipping authorities. When Guzmán’s son, Edgar Guzmán, was gunned down in the parking lot of a Culiacán shopping center in 2008, the rivalry turned into a blood feud within the Sinaloa cartel that triggered an explosion of violence, Dudley said. The chain of events eventually claiming Arturo Beltrán-Leyva, 48, the self-styled “boss of bosses” of Mexico’s underworld, who was killed in a shootout by Mexican marines with DEA support in December 2009.

[Mexican agents arrest brother of Beltrán Leyva, drug lord killed in raid]

Both El Mochomo and El Chapo face an overlapping list of cooperating government witnesses and U.S. prosecutors, Assistant U.S. Attorney Andrea Goldbarg of Brooklyn, and her successor as deputy chief of the Justice Department’s Narcotics and Dangerous Drug Section, Amanda Liskamm.

One cooperator, Juan Carlos Ramirez-Abadia, or “Chupeta,” 54, was a leading supplier of cocaine to Sinaloa and BLO through Colombia’s Norte del Valle cartel. He directed the production of business ledgers and was also prosecuted by Goldbarg. DEA agents helped obtain “the forfeiture of hundreds of millions of dollars” of Ramirez-Abadia's purported billion-dollar fortune, U.S. authorities said when he was extradited in 2008 and remains under U.S. indictment.

[Flores drug indictment gives clues to Mexican cartels’ networks in the U.S.]

U.S. authorities also appeared to have cut deals with a relatives of the No. 2 Sinaloa leader and potential Guzmán heir, Ismael “El Mayo” Zambada García. Mayo’s brother, Jesus “El Rey” Zambada, was cited by prosecutors in a February 2016 pretrial hearing as a witness against Beltrán-Leyva.

Mayo’s son, Vicente Zambada Niebla, 41, agreed not to contest the forfeiture of nearly $1.4 billion — including cash, real estate, businesses, vehicles and other property — and cooperate with U.S. authorities while pending sentencing of 10 years to life in prison, a federal plea deal made public in 2014 in Chicago showed.

[Son of Mexico drug lord turns informant]

Combined, the prosecutions mark successes in U.S. and Mexican efforts to neutralize “high-value targets,” strengthen Mexican security forces and send a message that “impunity does not last forever” for drug capos, Dudley, the co-director of the Insight Crime think tank, said.

The prosecutions may have made little headway in reducing consumption or trafficking, Dudley said, but have aided authorities by mapping relationships among politicians, security forces and organized crime to reduce collusion.

Former U.S. prosecutors and DEA officials said that while the string of multibillion forfeitures may be largely symbolic, it was not out of the question that the stepped up pursuit of big-dollar judgments could give the government another lever in dealings with foreign governments, through the promise of sharing a cut of revenue, or by targeting economic assets or banking practices.

For example, Britain-based banking giant HSBC in December agreed to a $1.9 billion payment to settle money laundering charges, in which U.S. authorities said that between 2006 and 2010, Sinaloa, Norte del Valle and other drug traffickers laundered at least $881 million in tainted drug money.