(CNN) Hearing "I told you so" always stings, perhaps never more than when one of the world's most-wanted men slips out of a maximum-security prison through a mile-long tunnel that took months in the making.

Former Drug Enforcement Administration agent Phil Jordan told everyone so.

When Sinaloa cartel chief Joaquín Archivaldo Guzmán Loera, aka " El Chapo ," was arrested in February 2014 -- after 13 years on the lam following another prison escape -- the ex-head of the DEA's El Paso Intelligence Center told CNN that the arrest was a big deal, but only if Mexico shipped the kingpin to its neighbor to the north.

"It is a significant arrest, provided he gets extradited immediately to the United States," Jordan said. "If he does not get extradited, then he will be allowed to escape within a period of time. ... If he is, in fact, incarcerated, until he gets extradited to the United States, it will be business as usual."

Suffice to say, Jordan, who spent more than 30 years with the DEA, was not shocked by this week's news that Guzman had escaped.

"No, I'm surprised it took a year for him to escape," he said, interrupting his thought to correct himself. "Before he was allowed to escape."

Like many observers, Jordan says he believes Guzman had help in his jailbreak , and not just from those who dug the tunnel, ventilated it and laid tracks for a modified motorcycle. No, Jordan thinks Guzman had help on the inside, much like he did during his 2001 escape in which dozens of prison workers, including the warden, were prosecuted.

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In fact, Jordan suspects Guzman's entire arrest was a sham, "a little show and tell" to project the impression that Mexico was making strides in its fight against the cartels. Why else would a man who traveled at times with an 800-member security detail be caught with his family and a single bodyguard in the resort town of Mazatlán?

The story of Guzman's 2014 capture was "absolute BS," he said. "They don't capture Guzman unless they've made a deal with Guzman not to extradite him to the United States."

And the extradition? "It was never going to happen," Jordan said.

A matter of sovereignty or pride?

There is no shortage of hypotheses about why Guzman wasn't extradited to the United States. Some analysts say Mexican President Enrique Peña Nieto wanted to, contrary to his predecessor, limit U.S. involvement in Mexico's drug war and felt having the United States try and imprison Mexico's top criminal would be a blow to the country's ego and sovereignty.

"It was, I believe, a source of national pride to say that, 'We've got this. This is our situation and we can handle it,' " said Sylvia Longmire, author of "Cartel: The Coming Invasion of Mexico's Drug Wars."

Ex-President Felipe Calderón had been viewed as weak because he relied so heavily on U.S. assistance, and Longmire said she believes Peña Nieto "wanted to take control of the drug war back."

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A sounder hunch is that former Attorney General Jesús Murillo Karam scuttled any potential deal. While there's no shortage of conspiracy theorists alleging Mexican officials feared El Chapo might dish dirt on the country's politicians, Murillo Karam publicly said he disapproved of the United States cutting deals with criminals -- as it did in 2013 with Jesús Vicente "El Vicentillo" Zambada Niebla, the son of Guzman's top lieutenant -- and not sharing with Mexico the fruits of the kingpins' cooperation.

Officially, Murillo Karam said Guzman would not be extradited until he finished serving his time in Mexico, a sentiment echoed by Ambassador Eduardo Medina-Mora . When Guzman escaped in 2001, he had served only seven of a more than 20-year sentence, and he racked up eight more charges before being recaptured last year.

The specter of a Supermax

The United States, where at least eight federal districts have rendered indictments against Guzman, submitted its formal request for Guzman's extradition in January or February, said CNN legal analyst Philip Holloway. Before Murillo Karam even received the paperwork, he "quite flippantly" said the United States could have Guzman in 300 or 400 years, when he finished serving his time in Mexico, Holloway said.

Mexican officials were "assuming he would serve out his prison time," the CNN analyst said. "We know better than that. We wanted to get him here so we could get him into a Supermax, where he'd spend 23 hours a day in a cell and not really be able to get out."

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Like Jordan, Holloway believes that Guzman's reach extends into "all facets of the Mexican government and the entire Mexican criminal justice system," he said. While Guzman also wields influence in the United States, he's not nearly as persuasive north of the border.

"We know that he has his tentacles into the U.S., but probably not to the degree that you could tunnel beneath the Supermax in Colorado," Holloway said.

Guzman was well aware of U.S. hopes to bring him before an American judge and jury, said Jordan, who is of the mind that Guzman's capture was orchestrated and the decision not to extradite him was made before he set foot in his cell.

"Tell me how many times John Gotti escaped or Al Capone escaped," he said. "(Guzman) knows that if he's sent to the U.S., the luxury hotel he built for himself in the Mexican prison is not going to happen."

Could treaty be ignored?

Article 15 of the U.S.-Mexico extradition treaty , signed in 1978, backs up Murillo Karam's claim that Guzman had to serve his time in Mexico before facing charges in the United States. That provision of the treaty states the U.S. or Mexico "may defer the surrender of the person sought" when the suspect is being tried or is already serving a sentence "until the conclusion of the proceeding or the full execution of the punishment that has been imposed."

But ex-U.S. Attorney General Alberto Gonzales said the treaty is more flexible than it may appear. Extradition requests are highly technical documents involving tricky, opaque and oft-controversial negotiations, he said, and it's possible Mexico would be willing to overlook the treaty in exchange for something -- not necessarily quid pro quo, but perhaps some useful intelligence or assets that it could employ in the drug war.

"Mexico could waive that if it was in their interest to do so," said Gonzales, now the dean of Belmont University College of Law.

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Gonzales emphasized that he had no inside knowledge of the machinations surrounding Guzman, but the Office of General Prosecutor, Mexico's equivalent of the U.S. Justice Department, "has to deal with its own bureaucracy when it comes to extradition requests. ... The people that make decisions in Mexico, I'm sure they had to consult with a number of people."

In 2007, when Gonzales headed President George W. Bush's Justice Department, Mexico agreed to extradite 15 suspected criminals, including Gulf cartel boss Osiel Cárdenas Guillén , in a move that was hailed as a great success in the U.S.-Mexico drug war partnership. It was the product of extended talks, the ex-attorney general said.

"That took time. It took a lot of secret negotiations and discussions," Gonzales said, explaining he notified neither DEA Administrator Karen Tandy nor Ambassador Antonio Garza that the talks were unfolding. "You want to keep the number very small in terms of who knows about possible extraditions."

'Anything's possible'

Gonzales suspects there were similar high-level discussions regarding Guzman, he said.

Mexico is rightly defensive of its sovereignty, and there are several possible scenarios that might have played out, Gonzales said. Because Mexico has long bristled at paternalistic U.S. inclinations to wag its finger over corruption, it could have decided it didn't need the "interference of another country," or it could have played the pot-calling-the-kettle-black card, raising the issue of escaped convicts Richard Matt and David Sweat and asking, "What about what happened in New York a month or so ago?"

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Or Mexico could have, as Murillo Karam said, honestly wanted Guzman to serve his time in Mexico first, Gonzales said. It's tough to say for certain, but you can be sure that there was behind-the-scenes bartering over El Chapo's fate following his 2014 arrest, he said.

What's less clear is what happens now.

Speculation abounds over Guzman's whereabouts. Did he leave the country? Has he sought refuge in the unsavory mountainous terrain of Sinaloa state, where he was raised and from where he thwarted many attempts to apprehend him? If he's captured again, would an embarrassed Mexico finally agree the Americans are better equipped to keep Guzman incarcerated?

"Anything's possible," said Holloway, the legal analyst.

Yet there is one more possibility that looms large, he said.

"I really don't think we're ever going to see him again."