Part 4: The Last Mafia Boss of Boston

Summary

Scratch & Win: Part 4 – The Last Mafia Boss of Boston

Release Date: February 12, 2025
Host/Author: GBH News
Produced by: Isabel Hibbard and Ian Coss
Executive Producer: Devin Maverick Robins
Distributed by: PRX

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Introduction

“Scratch & Win” delves deep into the intricate tapestry of American gambling history, focusing on the rise and fall of Boston’s most formidable Mafia family. In Part 4: The Last Mafia Boss of Boston, listeners are taken on a riveting journey from the shadowed alleys of 1970s Boston to the corridors of power within the FBI. This episode meticulously unpacks the FBI’s strategic assault on organized crime, the pivotal role of the state lottery, and the enigmatic figure of James "Whitey" Bulger.

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Background: Organized Crime in Boston

The tale begins in the early months of 1979 when FBI photo specialist Bill Sheparly and his colleague John Gill infiltrate Boston’s notorious North End, specifically targeting 98 Prince Street, the epicenter of the local Mafia and illegal numbers game operations.

Nomi Frye [01:00]: "The North End was an isolated and insular place surrounded by water and cut off from the rest of the city by six lanes of elevated highway."

The North End, once a vibrant Italian enclave, was a fortress of tradition where Mafia influence thrived unchallenged, providing a stark contrast to the emerging state-run gambling enterprises.

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The FBI’s Strategic Assault

The FBI, under the guidance of Attorney General Robert Kennedy, had been amassing a robust toolkit to combat organized crime, culminating in the Racketeer Influenced and Corrupt Organizations Act (RICO). This legislation allowed for the prosecution of entire criminal organizations rather than just individual members.

Nomi Frye [07:00]: "With RICO, if you could prove a pattern of criminal activity connected by a single criminal enterprise, then you could prosecute everyone involved at once, root and branch."

Sheparly and Gill were integral to this nationwide offensive, representing just two of the many agents mobilizing to dismantle entrenched Mafia operations across the country.

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Operation at 98 Prince Street

The operation centered on installing surveillance equipment at 98 Prince Street. Initial attempts to discreetly monitor the premises faced setbacks, including the discovery of hidden cameras by Mafia boss Gennaro Angiulo.

John Gill [03:19]: "We knew it was all over."

Undeterred, the team pivoted to using a specially modified 1968 Chevy with a concealed camera to capture continuous footage from the outside, while simultaneously embedding an audio bug inside the premises.

John Gill [05:29]: "The camera car could get a clean shot up to about 100ft out."

This dual approach was critical in gathering the comprehensive evidence needed to build a airtight RICO case against the Angiulo family.

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Key Figures: Gennaro Angiulo and James "Whitey" Bulger

At the helm of the Mafia operations was Gennaro Angiulo, whose leadership was both fearsome and strategic. In parallel, James "Whitey" Bulger, a rising star in the Winter Hill Irish gang, maintained a delicate and clandestine relationship with the FBI.

Nomi Frye [17:28]: "Whitey Bulger was now the top figure in the Boston crime world, and the numbers was never really his specialty."

Bulger, referred to by the FBI as a "strategist" rather than an informant, provided invaluable intelligence that facilitated the FBI’s infiltration and eventual takedown of the Angiulo family.

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The Surveillance Operation

The covert surveillance operation was grueling. Agents like Sheparly adhered to a strict routine of swapping and charging multiple batteries daily to keep the surveillance equipment operational.

John Gill [24:05]: "We probably went through 25 to 30 batteries."

This relentless maintenance underscored the operation’s high stakes and the agents’ unwavering commitment. Despite technical challenges, including a near-disastrous battery explosion, the team persevered, capturing crucial audio evidence over months of meticulous monitoring.

John Gill [25:15]: "The battery blew up in his face."

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Trial and RICO Case

The amassed evidence culminated in a landmark trial in February 1986, where Gennaro Angiulo and his brothers were convicted under the RICO statute. This was one of the first major RICO cases that successfully prosecuted an entire crime family rather than just individual members.

Ernie Danisko [32:19]: "This was the first one that dealt with an entire crime family like that."

An audibility hearing was pivotal in establishing the legitimacy of the taped evidence, despite initial challenges in presenting the fragmented and often inaudible recordings.

Nomi Frye [33:27]: "Without the tapes, there is no case."

The conviction marked a significant victory for the FBI, signaling the effectiveness of coordinated legislative and tactical efforts against organized crime.

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Impact on the Gambling Industry and State Lottery

The downfall of the Angiulo family had a profound impact on Boston’s illegal gambling landscape. The state lottery, having launched its own numbers game as a legal alternative, found itself at a strategic advantage as organized crime’s influence waned.

Kevin Weeks [40:11]: "The government sees money to be made, they get involved in it. They're the biggest gang in the country."

The transition from illicit, community-driven numbers games to state-controlled lotteries transformed the gambling industry, reducing the reliance on violence and fostering a more regulated environment.

Nomi Frye [41:05]: "The game was held together by violence, or at least the threat of violence... It was part of the community in a way that no state lottery could ever be."

However, this shift also opened debates on the ethical implications of state involvement in gambling and its role in perpetuating a legalized form of gaming.

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Conclusion

“Scratch & Win: Part 4 – The Last Mafia Boss of Boston” offers a comprehensive exploration of the intricate battle between the FBI and Boston’s organized crime. Through detailed storytelling, firsthand accounts, and archival recordings, the episode not only chronicles the fall of Gennaro Angiulo but also highlights the broader socio-economic transformations influenced by state-run lotteries and the enduring legacy of figures like Whitey Bulger.

Ernie Danisko [40:20]: "You had housewives and little old ladies and everybody... it was well understood."

This episode serves as a poignant reminder of the complexities surrounding legal and illegal gambling, law enforcement’s evolving strategies, and the profound impact of legislative measures like RICO on dismantling entrenched criminal networks.

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Notable Quotes

• John Gill [05:29]: "The camera car could get a clean shot up to about 100ft out."
• John Gill [24:05]: "We probably went through 25 to 30 batteries."
• Ernie Danisko [32:19]: "This was the first one that dealt with an entire crime family like that."
• Kevin Weeks [40:11]: "The government sees money to be made, they get involved in it. They're the biggest gang in the country."
• Nomi Frye [41:05]: "The game was held together by violence, or at least the threat of violence... It was part of the community in a way that no state lottery could ever be."

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Further Resources

For those interested in a more in-depth exploration, the episode references the book “The Rise and Fall of a Mafia Family” by Gerard O'Neill and Dick Lehrer, which provides a comprehensive account of the events discussed. Additional interviews with FBI agents and prosecutors, including Jane Serene Raskin and John Voorhees, offer nuanced perspectives on the case's complexities.

For more episodes, archival footage, and full transcripts, visit gbhnews.org/scratchandwin or check out the GBH YouTube channel.

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Artwork by Bill Miller and Mami Hawa Bao. Closing song "You Made Me Love You" performed by Massachusetts State Treasurer Bob Crane. “Scratch & Win” is a production of GBH News and distributed by PRX.

Transcript

[Nomi Frye]

I'm Nomi Frye. I'm Vincent Cunningham.

[Vincent Cunningham]

I'm Alex Schwartz. And we are Critics at Large, a podcast from the New Yorker. Guys, what do we do on the show every week?

[Alex Schwartz]

We look into the startling maw of our culture and try to figure something out.

[Vincent Cunningham]

That's right. We take something that's going on in the culture now. Maybe it's a movie, maybe it's a book, maybe it's just kind of a trend that we see floating in the.

[Nomi Frye]

Ether and we expand it across culture as kind of a pattern or a template.

[Alex Schwartz]

We talked about the midlife crisis, starting with a new book by Miranda July.

[Nomi Frye]

But then we kind of ended up.

[Alex Schwartz]

Talking about Dante's Inferno.

[Nomi Frye]

You know, we talked about Kate Middleton, her so called disappearance. And from that we moved into right wing conspiracy theories.

[Alex Schwartz]

Alex basically promised to explain to me why everybody likes the Beatles.

[Vincent Cunningham]

You know, we've also noticed that advice is everywhere. Advice columns, advice giving. And we kind of want to look at why. Join us on Critics at Large from the New Yorker. New episodes drop every Thursday. Follow wherever you get your podcasts.

[Nomi Frye]

In the early months of 1979, Bill Sheparly, a photo specialist out of the FBI's Boston office, was sent into the city's north end with a simple get a camera on their target. 98 Prince St.

[John Gill]

It was a typical old neighborhood, so anything we tried to do, we would be picked up pretty darn quick.

[Nomi Frye]

The North End is our little Italy, the place to go for a cannoli, a plate of fried Calamari. But in 1979, it was not the dressed up tourist attraction it is today.

[John Gill]

Yeah, well, this area over here is.

[Ed Quinn]

Different than a lot of other areas.

[Kevin Weeks]

You know, it's very, very closely knit.

[Nomi Frye]

Then it was an isolated and insular place surrounded by water and cut off from the rest of the city by six lanes of elevated highway. And it really did look like a slice of the old world stuck under the edge of the new world. That's the way we are. Italian people. A place where young men clustered on stoops in the afternoon and vendors worked the streets.

[John Gill]

And I mean, you know me, I.

[Nomi Frye]

Know you and me to know each other. Every time you come down here, we.

[John Gill]

Get acquainted more and more. Yes, I got plenty of good stuff here. What do you want?

[Nomi Frye]

Cucumbers, lettuce, tomatoes.

[Ed Quinn]

What kind of a shop is this? I don't understand Italian.

[Alex Schwartz]

You know, it was a very tight neighborhood. Italian neighborhood. Everybody knew everybody.

[Nomi Frye]

John Gill was part of that same FBI team, an organized crime strike force. Gill specialized in listening devices, bugs and wiretaps.

[Alex Schwartz]

You know, I used to play telephone man.

[Nomi Frye]

What do you mean by play telephone man?

[Alex Schwartz]

Well, you'd just go in acting like a telephone man and do what you had to do. You know, you could go up the poles or go into the boxes and nobody would pay any attention to you. But not really in the North End. What are the. What are all these Irish guys doing climbing up on our walls?

[Nomi Frye]

The reason that Sheparly and Gill were sent into this neighborhood, where they both clearly did not belong, was that 98 Prince street was the nerve center of the city's Mafia and also the city's illegal numbers game. Do you remember your first attempts to photograph 98 Prince Street?

[John Gill]

Yeah, we tried to put a camera in a storage type building.

[Nomi Frye]

Sheparly's first hidden camera was on a rooftop facing the back entrance of 98 Prince, disguised as a utility box. It ran for a few weeks in May of 1979, until one day a man stepped out of the building at 1:30 in the morning, looked up at the camera and waved.

[John Gill]

So we knew he found the camera somehow.

[Nomi Frye]

The man waving was Gennaro Angulo, head of Boston's Mafia family.

[John Gill]

So we knew it was all over. At that time.

[Nomi Frye]

Sheparly could see that the neighborhood was Angelo's shield. Anything that happened there got back to him somehow. Which meant that if they wanted to surveil the Mafia's headquarters, cameras in or on buildings were not going to work. They'd have to get creative.

[John Gill]

So it boiled down that our only option was to put a camera in a vehicle.

[Nomi Frye]

It would take some doing, but Sheparly believed the plan could work if they had the right car, the right camera, and of course, the right parking spot.

[John Gill]

The best car at the time would be about a 68 Chevy, which had a six cylinder, not a V8.

[Nomi Frye]

Is that because the engine was small enough that there was still room in there for the camera?

[John Gill]

That's correct. It was up and down the street where a V8 was situated at a V angle. So we hunted around and we came up with two.

[Nomi Frye]

The cars were registered to fake names with addresses scattered around the Boston area. A high turnover apartment building in Jamaica Plain, A condo complex in Framingham. Places where, unlike the North End, people might not know their neighbors. And the whole operation would be kept entirely within the FBI team. No utility wires, no buildings, no local cops. Just a car parked on the street.

[John Gill]

And the camera we had to use was pretty big. So the cars, the Chevys we came.

[Nomi Frye]

Up with were perfect with a 200 millimeter lens placed right behind the grille. The camera car could get a clean shot up to about 100ft out. It wasn't quite a video camera, but it could take one frame per second, enough to give you a flip book style record of every person that came and went from 98 Prince.

[John Gill]

And fortunately there was a location on Prince street on the corner of Thatcher, so there'd be no other car in front of us.

[Nomi Frye]

Now they just had to snag that parking spot.

[John Gill]

It was a matter of just cruising around and waiting for it to open.

[Nomi Frye]

So you had multiple agents circling that.

[John Gill]

Block, just riding around waiting for it because we had to get it.

[Nomi Frye]

And once you got a car in that spot, you held onto that spot for months.

[John Gill]

Four months we owned that spot. No one else was going to get it, no matter what.

[Nomi Frye]

The camera was in place. But that was just the first step. If the FBI was going to make their case, they would need audio too. And that could not be captured from a car. It had to be from inside 98 Prince street from GBH News, this is scratch and win the making of America's most successful lottery. I mean coss. When the Massachusetts lottery launched its own version of the numbers game, it did not immediately crush the illegal competition. The Angulo brothers still had their regular customers and their huge network of bookmakers. By some estimates, the Boston numbers racket was the most profitable mafia run gambling operation in the entire country, bringing in tens of thousands of dollars a day even after the lottery started. But it turned out that the state lottery was really one half of a pincer movement that closed in with an almost coordinated precision. The other half was the FBI. Because in the very same years that the lottery was ascendant, growing by leaps and bounds, the feds were adopting a new strategy towards organized crime. No more busting bookies and low level players. They were going straight for the top. This is part four. The last Mafia boss of Boston, Bill Sheparly and John Gill were just two foot soldiers in a nationwide assault on organized crime. They mobilized in the 1970s and triumphed in the 1980s. But in many ways, that assault began in the 1960s with Attorney General Robert Kennedy.

[Ed Quinn]

In too many major communities of our.

[Nomi Frye]

Country, organized crime has become big business. Here he is speaking at the University of Georgia law School in 1961, shortly after he took office.

[Ed Quinn]

Tolerating organized crime promotes the cheap philosophy that everything is a racket. Unless the basic attitude changes here in this country, the rackets will prosper and grow. Of this I am convinced.

[Nomi Frye]

It Took years for Kennedy's zeal to produce results, but we can see the beginnings of it right there. In 1961, he went to Congress and asked for new tools to prosecute organized crime. He got them. The Travel act, the Federal Wire act, the Interstate Transportation of Wagering Paraphernalia Act. The toolkit continued to grow over the decade, culminating in the ultimate weapon, rico. The Racketeer Influenced and Corrupt Organizations Act. The challenge of prosecuting the mobile was that historically you had to tie individual people to individual crimes. But for the most part, the leadership didn't get their hands dirty with that stuff. With rico though, if you could prove a pattern of criminal activity connected by a single criminal enterprise, then you could prosecute everyone involved at once, root and branch. Also in the toolkit, there was improved technology for surveillance cameras, listening devices, wiretaps. There were new legal powers to use that technology, along with the new witness protection program to encourage informants to come forward. The pieces were all in place, waiting for a test case to bring them together and demonstrate their power in many ways. That first test case was in Boston, and the target was the short spectacled and big talking underboss of the local family, Gennaro and Giulo. In 1979, Agent Bill Sheparly worked out his system for monitoring the entrance to 98 Prince with a camera car. In 1980, the attention turned to getting ears inside. The idea was that with round the clock video outside and audio inside, the FBI would be able to identify who was in the office and who was speaking on those tapes. It took a year to work out the details and to get legal approval for the surveillance. In January of 1981, the plan was underway. The story of this operation is told very well in a book from 1989 called the The Rise and Fall of a Mafia family, written by two former Globe reporters, Gerard O'Neill and Dick Lehrer, to a large extent, be relaying and retracing their reporting. But there were some key participants who were not yet ready to tell their stories. In the 1980s when the case was still fresh, how did you get into 98 Prince Street?

[Alex Schwartz]

Picked the lock.

[Nomi Frye]

That includes the audio specialist who entered the building and installed the actual listening device. John Gill.

[Alex Schwartz]

Actually it was very cheap lock. Probably the cheapest lock you could put on it was a builder's grade lock, no alarms.

[Nomi Frye]

Were you surprised how little physical security there was in the building?

[Alex Schwartz]

Yeah, I was, I was, I was shocked. But like I say, they were depending on the neighborhood. That's my only explanation for it. I think he Felt that anything happened in the north end, he'd hear about it.

[Nomi Frye]

By the judge's order, the FBI team had 30 days to plan. Replace the bug. The first attempt failed. There was a group of men lingering on the street late into the night, so the agent in charge called it off on the second attempt. They had radio trouble and called it off again on the third attempt. Everything looked good. The agents made it all the way into the recessed entryway of 98 Prince street. But standing there at the door, they could hear faint voices inside. Once again, they called it off. The fourth attempt was on a Sunday night. The temperature had stayed below freezing for days and no one was out on the street.

[Alex Schwartz]

Everything was quiet.

[Nomi Frye]

This time. The agents had also tailed Angullo and some of his key lieutenants to make sure no one would be in the building. At around 2am they made their approach. Once again the agents got to the entryway and once again they heard voices inside. They listened for a moment, then they picked the lock and went in anyway.

[Ed Quinn]

This is WEI Boston, Greater Boston's number one station for news.

[Alex Schwartz]

We found out that they played a radio in there 24 hours a day.

[Nomi Frye]

That was the voices they were hearing. Talk radio Wei Vincent Pirro has been.

[Ed Quinn]

Indicted on extortion charges and the jury resumes deliberating today in the mail fraud trial, appointed former Boston political aide Robert Toomey.

[Nomi Frye]

Could you describe the inside of 98 Prince Street?

[Alex Schwartz]

It was almost like a clubhouse, you know, they had a big dining room table. In the back was a. It was almost a commercial kitchen. Gigantic stove. You could cook a buffalo back there.

[Nomi Frye]

Other than that stove, the place was pretty unimpressive. Fake wood paneling, drop ceiling. The carpets were thin and worn. The furniture was cheap, covered in white vinyl. This is not where they spent their money to help place the microphones. Ed Quinn, the case agent, had intel from informants that showed the layout of the room and where Gennaro and Giulo usually sat.

[Alex Schwartz]

We had a diagram we got from the case agent of where he thought they would be talking. And that's where we put them.

[Nomi Frye]

The installation got off to a good start. There was even a ladder left in the Angulo's office that the agents were able to use. Pretty convenient. But once he pushed up the tiles on that drop ceiling, Gil found a problem.

[Alex Schwartz]

They had done their own wiring and it was just so screwed up and squirrely, we were afraid of burning the place down.

[Nomi Frye]

As far as Gil could tell, Angelo was stealing electricity from another building. They never figured out the whole scheme, but the wiring was definitely not up to code.

[Alex Schwartz]

A wire that was supposed to be ground was hot. A wire that was supposed to be hot was ground. We just didn't want to take the chance.

[Nomi Frye]

The original plan had been to steal some power themselves, mostly for the wireless transmitter that would relay the audio signal to a nearby building. Instead, they'd have to go with plan B.

[Alex Schwartz]

We decided to leave it alone and go with the battery.

[Nomi Frye]

Gil installed a battery the size of a lunch pail. It would be good for 30 days, but no one knew if that would be enough time to get what they needed. The team padded the battery with insulation to hide any noise. They replaced the ceiling panels, reset the furniture, put the ladder back where they found it.

[Alex Schwartz]

Pick up any wire clippings, get out of there.

[Nomi Frye]

Before they left the case, agent Ed Quinn noticed a plaque on the wall over the desk. It read, it is better to remain quiet and be thought a fool than to speak and remove all doubt. It was good advice. Gennaro and Giulo rose to power out of an era of instability and violence.

[Ed Quinn]

Boston, during the 1960s. It was the scene of an all out gang war, a decade of violence.

[Nomi Frye]

It started as a feud between two Irish gangs, but soon involved the Italian crime families as well.

[Ernie Danisko]

What the Italians did was sit back and when things got dull, they would go out and commit a murder and the other side would retaliate.

[Nomi Frye]

Ernie Danisko is a longtime federal prosecutor, including on the Angiulo case.

[Ernie Danisko]

This went on, if I'm not mistaken, I think there were 63 gangland murder cases from the late 50s into the early 60s.

[Nomi Frye]

There were bodies in the street, bodies in the river, bodies in car trunks.

[Ed Quinn]

The battle was over territory. To the survivors went a multi million dollar network of illegal businesses and control over Boston's loan sharking and gambling operations.

[Nomi Frye]

There are actually two important figures who emerged out of this era and would dominate Boston's crime world in the decades to come. The first, of course, is Gennaro Angulo, head of the local mafia family. The second is a man you may have heard of, James Whitey Bulger, a man who has inspired film performances by both Johnny Depp and Jack Nicholson. But back then, Bolger was just known as Jimmy and he was a rising leader of one of the old Irish gangs, Winter Hill. What was Jimmy Bulger's relationship with Jerry Angullo like?

[Kevin Weeks]

They had a working relationship. They didn't have a trusting relationship.

[Nomi Frye]

Kevin Weeks was a close lieutenant of Whitey Bulger beginning in the late 70s. By that time, the Boston gang wars were over. But Bulger and Njulo were clearly rivals. They both had gambling operations with Angelo in the north end and Bolger in South Boston. Weeks describes it as a delicate truce.

[Kevin Weeks]

Jerry and them never faced anyone like Winter Hill. You know, I mean, they had a lot of guys and they all shoot us.

[Nomi Frye]

Winter Hill did.

[Kevin Weeks]

Winter Hill did, yeah. Wall killers. So it was, you know, everybody got along. No one wanted a war.

[Nomi Frye]

What Weeks didn't know at the time was that his boss was working with the FBI. Bulger didn't like the term informant. He insisted on being called a strategist. Starting around 1975, Bulger fed the FBI information about Angullo. In exchange, he got protection and more. Just a few months before the audio bug was installed, Bulger and an associate went to meet with Angullo at 98 Prince street on instructions from their FBI handlers. They were supposed to confirm whether the building had an alarm system. They couldn't. But they did return with a hand drawn floor plan of the Angulos office. When the FBI submitted its application for the surveillance operation, Bulger was listed as an informant. With everything that's come to light since, it's now unclear just how important Bulger's evidence was. I can't say for sure if that's how the FBI knew where to put those hidden microphones, but it was part of the intel. And in any case, what follows is a strange chapter in a decades long ethnic rivalry. The Irish mobster helping a team of largely Irish FBI agents take down the city's Italian crime family. And in the process doing a great service to the Irish run state lottery. There may not have been a gang war in the streets this time, but Bolger was making a move. What did he look like when he got mad?

[Kevin Weeks]

Well, I mean there's two phases of mad, Maddie at the average person and stuff, nobody thing. But then when he got really mad at someone, you know, his eyes, I mean, he had blue eyes and they turned red, all red around them. The conover's lip would curl up and his voice would get a little lower and softer, deeper, and, you know, there was a problem.

[Nomi Frye]

Did you know how long the surveillance was going to last?

[John Gill]

No.

[Nomi Frye]

Bill Sheparly, the camera guy, had an.

[John Gill]

Idea to be a couple of months, but of course they weren't getting good evidence. Jerry wasn't talking to anyone really.

[Nomi Frye]

Starting In January of 1981, the FBI listened in every day as Jerry Angiulo's younger brother Frankie opened up the office on 98 Prince St. Frankie was a Smoker and they could hear as he coughed and spat in the sink, then put on a pot of coffee. Other brothers would come and go during the day. Jimmy Jones, Mikey Nicolo, sometimes Danny. But Frankie handled most of the day to day numbers business and unfortunately he didn't talk much. Bookmakers would arrive, bring in huge amounts of cash, but Frankie would greet them with just a few words, usually Nothing explicit. Around 4pm Gennaro and Giulo himself would arrive in a red two door AMC Pacer with his name on the license plate. For a few hours he would hold forth with whoever was there until 7:30pm at which point the boss would quiet the room to watch, of all things, WGBH Channel 2 Public Television.

[Alex Schwartz]

Channel 2, Boston Public Television for New England.

[Nomi Frye]

Apparently the Mafia leader was a great fan of the Wild, Wild world of Animals with its stories of sly and ruthless creatures.

[Ed Quinn]

Few animals have more clearly proven themselves a menace to man than the African crocodile.

[Nomi Frye]

The FBI could also hear the brothers watching Celtics games, though they always rooted against the home team since they did handle some sports betting on the side and that's who their clients tended to bet for. The house wins when the home team loses. What the FBI didn't hear, at least at first, was anything incriminating.

[John Gill]

So they kept getting approval to extend the bug.

[Nomi Frye]

The operation went all through the winter and into the spring, just waiting for the evidence that could make their case. For the technical agents that mostly meant changing a lot of batteries.

[John Gill]

We needed six Sears Diehy batteries to run the whole system.

[Nomi Frye]

Six car batteries essentially to power that camera setup. And they all had to be changed every 24 hours. So every night around 2:30 in the morning, one agent would pull the car out of that perfect parking spot and another agent would be there in another car waiting to pull right in. That became Sheparly's routine. His uniform was flannel and jeans with a snub nose revolver tucked in the waist. He grew out his beard. He was basically nocturnal. Just an endless cycle of swapping cars and charging batteries.

[John Gill]

We probably went through 25 to 30 batteries. So I was going and buying all these batteries. Like Sears, they loved it. They didn't know what I was doing with them.

[Nomi Frye]

Those old batteries would slowly release fumes that could be explosive. Once, just once, when he was setting one up to charge, Sheberly got careless and made a bad connection, causing a spark.

[John Gill]

It was like a cherry bomb going off.

[Nomi Frye]

The battery blew up in his face.

[John Gill]

I never made that mistake again. And of course it woke you up.

[Alex Schwartz]

I remember him working with all those batteries. And he was running around with jeans with holes in them from the battery acid.

[Nomi Frye]

John Gill, the audio guy, he worked.

[Alex Schwartz]

His butt off, but he never slept at night.

[Nomi Frye]

The batteries for the audio bug also had to be swapped out three times over the course of the operation. That meant the whole routine of unlocking the door, going into 98 prints, and going up above the ceiling panels. Every time the agents went in there, there was a chance of being seen. And afterwards they would wait eagerly to hear if the daily activity continued as normal.

[Alex Schwartz]

We picked up on the wire that they suspected they might be. There might be something there. And I went over. There was across the street, acting like I just came out of a bar, kind of looking in the window to see if they were looking. But if they were looking, they weren't looking in the right places. I didn't see any roof panels being pulled or walls being torn down. So I was happy.

[Nomi Frye]

And eventually things started to pick up. This is audio from the bug recorded at 98 Prince Street.

[John Gill]

If you fuck someone that's close to left, I'm going to give you a shake now, so you just understand.

[Nomi Frye]

They captured shakedowns, threats, and specific amounts owed in gambling debts. They also heard Gennaro Angiulo's poetic musings on the life of crime. Like, I wouldn't be in a legitimate business for all the fucking money in the world. Or, when a guy knocks you down, never get up unless he's gonna kill ya. And Julo would often punctuate these pronouncements with the line, you understand American? To the untrained ear, including mine, most of these recordings are totally unintelligible, especially with the talk radio running constantly in the background. But the human mind can do strange things. Once the agents heard enough hours of this chatter, the words started to click. The gambling, the loan sharking, all the makings of a RICO case were there. And then one night, an even bigger charge. Murder ordered by Angullo himself. Quote, meet him tonight. I hope it's tonight. Just hit him in the fucking head and stab him. Okay? The jeopardy is just a little too much for me. You understand American? Okay, let's go. In May of 1981, after four months of listening in, the FBI raided 98 Prince Street. They would try to make a case with the evidence they had. Was it weird going in there in broad daylight after having been in there surreptitiously so many times?

[Alex Schwartz]

Oh, very much so, yeah. You could see what color everything was.

[Nomi Frye]

John Gill went in that day as part of the technical team, they found a Safe upstairs in 98 prints wedged into a fireplace.

[Alex Schwartz]

And we beat it up with a sledgehammer and we had a locksmith come in and drill it.

[Nomi Frye]

The safe had $327,000 cash, plus jewelry and bonds. This raid was about four years exactly since the state lottery had launched its competing numbers game. At that time, the State claimed that 85% of players with the illegal game would switch right over to theirs. But given how much money was in that safe, it seems the Angulos were still doing all right. Soon after the raid, an FBI agent on the case named John Morris met up at a downtown hotel with their prized informant, Whitey Bulger. Morris brought along a tape. Bulger brought two bottles of wine. The agent and gangster drank to Angelo's misfortune while listening to the Mafia boss boast on the tapes and deride Whitey Bulger convinced of his own invincibility. Apparently, Morris got so drunk that Bulger had to drive the FBI agent home in his own government car. It took a long time for the other shoe to drop. The FBI spent months enhancing, deciphering and Transcribing the audio tapes. 850 hours of tapes. Prosecutors spent more than two years preparing the case. And amazingly, Gennaro Angiulo and his brothers never tried to run. He felt safe enclosed in the North End, where he had weathered so many prosecutions before. So he kept to his routine, including dinner at his go to Italian restaurant, Francesca's, until one night in 1983, around.

[Ed Quinn]

9 o'clock, the back room here at Francesco's is cleared out and a white tablecloth is set with silver and china. Jerry Angelo walks in and takes his place at the head of the table. Several men join him for dinner and offer him a toast. It's like a scene right out of the movies. From the outside looking in, it appears to be a group of gentle old men just sitting down for a casual dinner. None of them threaten.

[Nomi Frye]

On September 19, 1983, Angullo sat down for a dinner of pork chops. His two brothers had linguine and clam sauce. Partway through dinner, the FBI's case agent, Ed Quinn, approached the table.

[Ed Quinn]

The subject.

[Nomi Frye]

Three of them were arrested at Francesca's.

[Ed Quinn]

Francesca.

[Ernie Danisko]

Francesca's restaurant.

[Nomi Frye]

The U.S. attorney's office announced the arrests the next day at a press conference.

[Ed Quinn]

I think you can answer that. They refused to be fingerprinted and photographed.

[Nomi Frye]

They also announced the charges and all.

[Ed Quinn]

The defendants, including Gennaro and Giulo and Victori. Nicolo Angullo Donato, Angiulo, Samuel, Granito, Francesco.

[Nomi Frye]

I mentioned before that this case was historic and here's why. It was the whole family, the whole organization tied together under one charge.

[Ed Quinn]

RICO, Title 18, United States Code, Section 1961 4. That is a group of individuals associated.

[Ernie Danisko]

In fact, at this point in time, it was was the first case that dealt with an entire crime family like that. This was the first one.

[Nomi Frye]

Ernie Danisko was one of three prosecutors on the case.

[Ernie Danisko]

So you couple that with the longevity of this group and the fact that they were notorious, I mean, notorious for the capital N. It was just difficult to imagine that these guys would go down.

[Ed Quinn]

His first arrests were for gambling, later for beating up a treasury agent and.

[Nomi Frye]

Then assault on a. Angelo's operation had been raided before. He'd been arrested before and charged before in the 1960s and the 70s, but nothing seemed to stick. The cases always fell through. When Angelo was escorted out of the restaurant that September night, he shouted out confidently, I'll be back for my pork chops before they're cold. As Danisko recalls, Angelo's lawyers went in pretty confident too, because by this time they had heard the tapes from 98 Prince street with the garbled shouting and constant radio noise. And they had told Angelo, no one can understand these tapes.

[Ed Quinn]

The big question mark in this trial are the secret tape recordings.

[Nomi Frye]

The prosecution knew this was a problem too.

[Ernie Danisko]

People yelling, people screaming, people talking over one another. And you got to know who's speaking.

[Ed Quinn]

One federal magistrate is quoted as saying, without the tapes, there is no case.

[Nomi Frye]

So the first big question in the trial was really procedural, but very important. Could the prosecutors give the jurors transcripts? The defense rejected this idea since of course the state had written those transcripts.

[Ernie Danisko]

And we had to have what was called an audibility hearing, where a magistrate listened to every single one of the tapes that we were going to use in the course of the case. And this was, this is brand new. No one had really done this before.

[Nomi Frye]

For the hearing they used two reel to reel tape players so they could go back and forth listening to one tape while they loaded up the next one.

[Ed Quinn]

All right, see, it's a man and I'm talking.

[Nomi Frye]

The hearing went on for weeks, tape after tape after tape, with a court appointed magistrate listening to everyone on a pair of headphones.

[Ernie Danisko]

And when conversations got really, really tense, when they were going to take someone out, they were whispering.

[Nomi Frye]

Danisko remembers on one of the key tapes, the one where Jerry and Julo ordered the murder, the voices were just barely, barely audible and they had a.

[Ernie Danisko]

Western, a Western movie on with it was a cattle drive or something, and you could hear the cows in the background booing.

[Nomi Frye]

Now all Danisko could do was watch the magistrate with his headphones on and hope the magistrate heard what he heard.

[Ernie Danisko]

So that he could write to the judge that the transcripts were fair and accurate representations of the words that were spoken on the tapes.

[Nomi Frye]

The transcripts were ultimately allowed, and not only could the magistrate understand the tapes, Jerry Angelo could understand them too, and.

[Ernie Danisko]

He was following along, and he knew that they were in deep trouble at that point in time.

[Nomi Frye]

To make a RICO case, the state has to prove a pattern of illegal activity. In this case, the big ones were gambling, loan sharking, and, of course, murder.

[Ernie Danisko]

The suggestion that I made was, let's start with the gambling business, because the evidence is overwhelming.

[Nomi Frye]

Once the gambling business was established, they could then show all the other crimes that the gambling inevitably led to.

[Ed Quinn]

This may be the first time that the corporate structure of organized crime has been so completely dissected for public view.

[Nomi Frye]

But the defense still insists testimony continued for eight months. There were occasional outbursts from Angullo at the defense table, but mostly he just sat there silent, his chin sticking forward. Danisko recalls one day a group of elementary school students came to observe the trial. Sitting right behind Angiulo, he turns to.

[Ernie Danisko]

The kids and he says, remember, kids, crime doesn't pay unless it's organized.

[Nomi Frye]

So he never lost his big mouth and his swagger, even through the trial. In February of 1986, five years after the bug was placed in 98 Prince Street, Gennaro Angiulo and three others were found guilty under the RICO Statute. It was, like I said, the first big RICO case. But ultimately, it was part of a wave of cases that toppled bosses in New York, New Orleans, Chicago, Kansas City, Los Angeles, Cleveland, Philadelphia, and elsewhere.

[Ernie Danisko]

And they were resigned. I've got to say that there was not a lot of personal outbreaks and, you know, outcry from them, and they were strong about it.

[Nomi Frye]

In a final flourish, Gennaro instructed his brothers to march out of the courtroom in lockstep, like an army platoon. He was 66 years old and would spend almost the rest of his life in prison. But he would live long enough to see at least one of his FBI adversaries join him there. It turned out that Whitey Bulger wasn't just feeding his handlers information, he was also paying them off. One agent ultimately served time. Another was granted immunity in exchange for testimony. So the whole Angiulo case, which was a Real success story for the bureau at the time. Looks a lot more muddled now. It's not so clear who was working for who, but the impact was undeniable. Yeah, it really seems like the prosecution came at this critical moment where the lottery was really ascendant. And then just at that moment, the whole numbers operation gets shaken to the core. It just seems like the kill blow at just the moment when it was weakest.

[Ernie Danisko]

I think that that's correct. That's a valid assumption.

[Nomi Frye]

Gennaro and Julo did not have a clear successor, and he had not passed on all the accumulated expertise of running a large scale numbers game. Smaller bookmakers kept operating, but none of them could bring the combination of scale, sophistication and ruthless force that Angelo had. Whitey Bulger was now the top figure in the Boston crime world, and the numbers was never really his specialty. By the late 1980s, a numbers bookie was caught on an FBI wiretap saying, quote, the business has been destroyed. I found there's an intensely generational quality to the numbers. I was born in the late 80s, and when I talk to people my age, they have no memories of it. Often they've never even heard of it. Talk to people my parents age, and the stories come pouring out. The numbers was everywhere, and then it was gone. In many ways, the state's takeover of the game was just as swift and ruthless as the white gangsters back in the 30s and 40s. Or as Kevin Weeks puts it, it's.

[Kevin Weeks]

The same old story. The government sees money to be made, they get involved in it. You know, they're the biggest gang in the country.

[Nomi Frye]

We should be clear eyed about what the old illegal numbers was. On a basic level, the game was held together by violence, or at least the threat of violence. That murder order that the FBI picked up was on a gambler who got in over his head and was under pressure to testify. Gennaro was willing to kill to make it all go away. The murder, by the way, was never carried out. The FBI tipped the man off. But even in its mobbed up form, there was a personal quality to the old numbers, a neighborhood quality that does not exist anymore. It was part of the community in a way that no state lottery could ever be.

[Kevin Weeks]

You had housewives and little old ladies and everybody, you know, they'd take 35 cents and they'd wrap it up in a paper towel with a number written on it, give it to the bookmaker.

[Nomi Frye]

And you didn't even need to say what it was for. It was just, it was understood.

[Kevin Weeks]

Yeah, I mean, the whole neighborhood was doing it. So it was well understood.

[Nomi Frye]

If the state lottery was just about combating organized crime, they could have stopped right there. They could have stopped at scratch tickets and the numbers game offer a legal alternative. Crack down on the rackets and leave it at that. But the state lottery was just getting started because lotteries were never just about stopping crime. They were about money. And in the 1980s, the state needed a new source of revenue like never before. For too long, the label of Taxachusetts has driven established industry and business from our state. Here in Taxachusetts, a tax revolt was underway and the lottery offered a way out. Don't you resent it when out of state friends kid you about living in Taxachusetts? That's next time.

[Ed Quinn]

You made me love you I didn't want to do it I didn't want to do it you made me want you and all the time you knew it I guess you always knew it you made me happy sometimes you made me sad but there were times dear you made me feel so bad.

[Nomi Frye]

The series is produced by Isabel Hibbert and myself, Ian Coss. It's edited by Lacey Roberts. The editorial Supervisor is Jennifer McKim with with support from Ryan Alderman. Mae Lei is the project manager, and the executive producer is Devin Maverick Robbins. I just want to recognize again the book the Underboss by Gerard O'Neill and Dick Lair. It was very important to making this episode and if you want more of this story, it's all there. I also interviewed a number of other FBI agents and prosecutors who you don't hear, but who helped shape my understanding of the case, including Jane Serene Raskin, John Voorhees, Fred Wyshak, and others who prefer not to be named. Thanks to all of you. For more info on the series and full Transcripts, go to gbhnews.org scratchandwin. You can also find videos of the episodes on the GBH YouTube channel with incredible archival footage. The artwork is by Bill Miller and Mami Hawa Bao. Our closing song is yous Made Me Love youe performed by Massachusetts State Treasurer Bob Crane. Scratch and Win is a production of GBH News and distributed by prx.

[Ed Quinn]

You know you made me love you and all the time you you knew it. Thank you.

[Nomi Frye]

From prx.