After three decades in the FBI, retired undercover agent can just be himself

Matthew Guglielmetti was serving as a union steward for Laborers Local 271, but was better known as a feared captain in the Patriarca crime family in Providence.

Michael McGowan had met wise-guys like him before. An undercover FBI agent, McGowan had infiltrated Rhode Island’s corrupt construction and union communities, posing as a parking magnate from the Midwest.

And there they were together, in 2001, at the Castaways seafood restaurant in Tampa, discussing business over fish and lobster. McGowan was soliciting the Mafia’s help in a concocted dispute with organized crime figures in Florida over a strip club.

“In two hours, I’ve got to pass this test,” McGowan recalled thinking.

The Guglielmetti meeting was a pivotal opportunity in what would become a lengthy undercover career, one McGowan recently retired from after 31 years with the bureau. His name is not well known — that’s the point — but in recent years, he’s had a hand in every major undercover case in the Boston area.

Think then-state Senator Dianne Wilkerson, Mafioso Carmen “the Cheeseman” DiNunzio, and Mexican drug lord Joaquin “El Chapo” Guzmán Loera.

In a recent interview with the Globe, he shared tales from the Guglielmetti operation, as well as other highlights — and some low turns — from his three decades working underground.

He reflected on an undercover program’s training that, in his view, has improved since he was thrown into an Italian social club in Philadelphia as a rookie, a young white Irish guy from Boston dressed in khakis and a starched shirt, only to be told to leave.

“Kid, I like you, but nobody knows what the [expletive] you’re doing here,” a man, in his 80s, had told him. “Get out.”

“We wouldn’t send someone in there like that nowadays,” McGowan said in the interview, recalling times his cover was blown.

Even at that meeting in Tampa, at the peak of his career, McGowan had feared that he was exposed, that Guglielmetti sensed something amiss. After all, Guglielmetti, known for his wits, was one of the few Mafiosi who evaded being caught on tape in the FBI’s famously-recorded 1989 induction ceremony in Medford.

“I shouldn’t be here,” Guglielmetti told McGowan at their dinner meeting.

“There’s the door, get up and go,” McGowan, playing the role of ruthless businessman, recalled telling him.

Guglielmetti stayed. They had dinner. They discussed McGowan’s business — Hemphill Construction, with an office in Johnston, R.I., — and his plans. And they left, each agreeing to meet again.

Guglielmetti was indicted in 2005, charged with participating in a drug conspiracy, based on an investigation that took root at that meeting in Tampa. He ultimately pleaded guilty to distributing 5 kilograms of cocaine and was sentenced to 11 years in prison. He was released in 2014.

Undercover operations had not always gone so swimmingly. McGowan, born and raised with street smarts in Haverhill, had been an FBI agent for only six months in 1987 when he was asked to help in an undercover sting of a violent cocaine ring in Philadelphia, and, he remembered, “it was embarrassing.”

Sure, he had been a police officer for five years already, in Vermont and Florida. His father and grandfather were cops, too. But this was different.

“I was thrown into the fire, day one,” he said, recalling how he made his way into social clubs and gambling houses. They wore tracksuits. He wore khakis. He went by the nickname Irish Mike. That’s when the old man told him to get out of there.

“The FBI, nationally, does undercover work better than anybody, but we also have failures and mistakes, and I’m the first to admit that,” said McGowan, in his 60s now. “The mistakes I made, other agents made, we made on the streets.”

Mistakes like trying to buy drugs from someone randomly on a street corner, only to be told, “not tonight officer, we’re busy.”

He once went into a strip club looking for a fugitive, and kept a picture of the target in his inside coat pocket. He sat there drinking Diet Coke, by himself. When he left to use the bathroom, he left the coat there. And when he returned, the picture was gone. He said he felt like 100 people were staring at him.

“You think when you’re undercover you’re invisible, but you’re not,” he said.

Fortunately, the only time he said he truly feared for his life was when he walked into Caffé Vittoria in the North End was dragged into a basement by three gangsters who pointed guns at him, believing he was being followed by the FBI. He sang the lyrics to “My Way,” playing on the jukebox, to calm his nerves — and he eventually left unharmed.

McGowan said some of his best lessons were from the informants who told him what not to do.

“It worked out for me, but I can’t believe it did work out,” he said. “Nowadays, we now make a learning environment, a training environment, so we don’t make those mistakes on the street.”

Those new training programs, according to McGowan, who had a say in the design of some of the programs, were not put into place until the early-1990s, after he had already been undercover for several years. But they have made a difference in the training of new undercover agents, he said.

It started with a national undercover school. Anyone interested would first need three years of experience with the bureau (McGowan went undercover at six months). Applicants would need a supervisor’s approval, would be interviewed by a coordinator, and would undergo psychological exams. Then, they would be put in real-life scenarios.

Even if they pass, they have to renew their certification every six months, and undergo psychological testing throughout.

What makes a good undercover? They would have common sense, good judgement, in McGowan’s view. Be humble. Not excited. Confident, but not cocky. Listens more than talks.

And once an agent goes undercover, they choose a “legend”: An agent’s story line, kept consistent in any role-playing, in any case, so that their story remains the same.

McGowan’s has two brothers, two sisters, and a love for golden retrievers. He said he once had a suspect admit to a homicide over a discussion of golden retrievers.

For years, he assumed his “legend” as Irish Mike, and then as The Walrus, a reference to his twisted mustache. In the end of his career he was El Viejo, or old man, a personality he took with him in 2010 into perhaps his most high-profile undercover meeting.

His team had successfully sent a confidential informant to infiltrate the Sinaloa drug cartel, headed by the violent El Chapo. The cartel wanted to expand to Europe, so McGowan and his team would pose as Italian gangsters, willing to help ship cocaine to Spain through fake fruit distribution companies, including one in New Hampshire.

First, there would be a meeting, in a 30th-floor oceanfront condo in the Fort Lauderdale area. El Chapo would send his chief negotiator — his cousin, Jesus Manuel Gutierrez Guzman.

McGowan went with a crew of younger agents who had undergone the new training: The hard-looking guy, meant to be the enforcer; the studious agent, meant to be the money guy; even an agent who would pose as the attractive woman.

“This is my Super Bowl,” he was thinking.

But something did not seem right. He had dressed the part of an Italian gangster, with a $5,000 suit, and a watch. But still, butterflies.

Five minutes before the meeting, McGowan went into a closet and found a purple velour bathrobe. He would wear this. It made more sense.

“What kind of FBI agent would dress like that?” he thought.

The deal went through. El Chapo’s crew agreed to send an initial shipment of 760 pounds of cocaine to Spain, which was intercepted by the FBI.

El Chapo was ultimately indicted, and his case in New Hampshire is one of several he faces in the United States for drug trafficking.

“We convinced them we were the real deal,” McGowan said.