Japan is currently creating a legal framework to operate casinos via a system of integrated resorts, but concerns persist that they’ll be prime targets for organized crime once they’re finally up and running by 2024.

“The yakuza have changed over the years, but one thing won’t change: They’re all about the money,” former FBI Special Agent James Stern says. “Tradition comes second.”

Many of the domestic yakuza syndicates were originally gambling federations and, as such, they’ve effectively been operating illegal casinos for decades. Indeed, it’s not hard to imagine that gambling resorts will be attractive targets for gangs.

Stern has spent decades of his life dealing with organized crime. He was born in Tokyo’s downtown neighborhood of Asakusa and moved to California when he was a child. He signed up for the U.S. Army as a young man and, later, the FBI. It was here where Stern was first introduced to the yakuza.

A crystal meth epidemic had infiltrated Hawaii in the early 1990s. The drug was extremely addictive and expensive to buy. The FBI suspected that Japan was an exporter of the drug. Stern, posing as an undercover Japanese American man named Jimmy Sato, befriended a low-ranking yakuza member called Koisuke Komine and gained his trust.

It wasn’t all plain sailing for Stern in his undercover role, though. Komine once got drunk and took off his shirt in the middle of a steak restaurant, proudly showing everyone his tattoos. He pointed a knife at Stern and ordered him to take off his shirt as well. This was a problem, since Stern had a recording device taped to his chest at the time.

After a few dead ends, Stern and his team managed to lure Mitsuo Yoshimura, the boss of a small-time gang, to Hawaii for a large transaction. After one disastrous meeting, the crew had one last chance to collect some hard evidence.

Stern had to be extremely careful to get Yoshimura to admit to a crime on tape — an admission that was impossible to take back once it had been made. The bureau had failed once before. In September 1985, the FBI arrested several members of the Yamaguchi-gumi syndicate who were trying to trade drugs for a rocket launcher.

During the subsequent trial, however, the defense argued that saying “hai” in Japanese could be translated as “I hear what you say,” not always “yes.” The gangsters were found not guilty.

This time around, the results were much better. Stern’s second meeting concluded successfully when Yoshimura made a clear statement of criminal intent.

The FBI team and local law enforcement carried out a raid on the room and arrested him. Yoshimura spent nearly a decade in federal prison after agreeing to a plea bargain. “Those were simpler days,” Stern says.

Upon leaving the FBI, Stern spent several years with Wynn Resorts, eventually becoming the casino operator’s chief of security. His experience in the casino industry has taught him a great deal about gangsters and anti-social forces all over the world, in places as widespread as Las Vegas and Macao. His time in the bureau had served him well.

Stern left Wynn Resorts earlier this year and now heads Global Gaming and Resort Security.

Stern organized the first working group between the FBI and the National Police Agency, and has been instrumental in getting the United States and Japan to work together on transnational cases. As a result, he prefers to treat domestic law enforcement agencies with respect.

However, he still expresses concern over the agencies’ ability to counter organized crime.

“Japan is a nation of laws and I’m sure that the police will be prepared,” Stern says. “But the casinos can’t trust the police to do everything. That won’t work well.”

Stern says that known gang syndicates in Japan will be easy to keep tabs on. Instead, law enforcement agencies need to pay closer attention to the syndicates’ associates: loan sharks, blackmailers, even girlfriends.

History has shown that a casino can be infiltrated in a number of different ways, regardless of how much security an operator introduces.

In 2006, a Yamaguchi-gumi Kodo-kai boss took over a school reunion website, Yubitoma, the Japanese equivalent of Classmates.com, and gained access to the private information of more than 3 million people.

If gang members are able to get access to surveillance cameras or know who’s checked into a hotel with whom, they have a great deal of information in their possession with which they could use for blackmail or extortion.

“Imagine if a gangster was able to get control over a VIP host — they could do a significant amount of damage,” Stern says. “There are many ways to skim money from a casino and criminals will easily figure out how to do it.”

So while Stern is optimistic about the establishment of casinos in Japan, he doesn’t think local law enforcement agencies will be able to stop gangs from seeking to infiltrate them. With a few more experienced people such as Stern and some sound advice, however, it may be safer to bet against them succeeding.

Dark Side of the Rising Sun is a monthly column that takes a behind-the-scenes look at news in Japan.

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