Scratch & Win

Ian Coss: In the early months of 1979, Bill Shopperle, a photo specialist out of the FBI's Boston office, was sent into the city's North End with a simple mission: get a camera on their target, 98 Prince Street.

Bill Shopperle: it was a typical old neighborhood. So, uh, anything we tried to do, we would be picked up pretty darn quick.

Ian: 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.

ARCHIVAL: Well, this area over here, it's different. A lot of the areas, you know, it's very, very closely knit

Ian: 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 onto the edge of the New World.

ARCHIVAL: That's the way we are, Italian people.

Ian: A place where young men clustered on stoops in the afternoon, and vendors worked the streets.

ARCHIVAL: I mean, you know me, I know you, and we get to know each other as I come down here, we get acquainted more and more

MUSIC: Fade in

ARCHIVAL: What do you want, cucumbers, lettuce, tomatoes

What kind of a shop is this?

I don't understand Italian,

John Gill: you know, it was a very tight neighborhood. It was an Italian neighborhood. Everybody knew everybody.

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

John Gill: You know, they used to play telephone man

Ian Coss: What do you mean by play telephone man?

John Gill: I mean, 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, uh, not really in the North End. What are the, what are all these Irish guys doing climbing about our, our walls?

MUSIC: Post

Ian: The reason that Shopperle and Gill were sent into this neighborhood where they both clearly did not belong, was that 98 Prince St was the nerve center of the city's mafia, and also, the city's illegal numbers game.

Ian Coss: Do you remember your first attempts to photograph 98 Prince Street?

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

Ian: Shopperle'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.

Bill Shopperle: so we knew we found the camera somehow.

Ian: The man waving was Gennaro Angiulo, head of Boston's mafia family.

Bill Shopperle: It was all over at that time.

MUSIC: Out

Ian: Shopperle could see that the neighborhood was Angiulo'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.

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

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

MUSIC: Enter

Bill Shopperle: the best car at the time would be about a 68 Chevy, which had a six cylinder, not a V8

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

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

Ian: 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.

Bill Shopperle: And the camera we had to use was pretty big. So the cars, the Chevys we came up with were perfect.

Ian: With a 200mm lens placed right behind the grill, the camera car could get a clean shot up to about 100 feet 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 St.

Bill Shopperle: 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.

Ian: Now they just had to snag that parking spot.

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

Ian Coss: So you had multiple agents circling that block?

Bill Shopperle: Just riding around, waiting for it, Because we had to get it.

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

Bill Shopperle: Four months we owned that spot. No one else was gonna get it no matter what.

Ian: 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 St.

MUSIC: Theme

Ian: From GBH News this is Scratch and Win: the making of America’s most successful lottery. I'm Ian Coss.

When the Massachusetts lottery launched its own version of the numbers game, it did not immediately crush the illegal competition. The Angiulo 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 ascendent, 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 4: The Last Mafia Boss of Boston.

MUSIC: Out

BREAK

Ian: Bill Shopperle and John Gill were two 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 60s with Attorney General Robert Kennedy.

ARCHIVAL: In too many major communities of our country, organized crime has become big business.

Ian: Here he is speaking at the University of Georgia Law School in 1961, shortly after he took office.

ARCHIVAL: Tolerating organized 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.

MUSIC: Enter

Ian: 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 tool kit continued to grow over the decade, culminating in the ultimate weapon: RICO, the Racketeer Influenced and Corrupt Organizations Act. The challenge of prosecuting the mob, 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 tool kit, 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 Angiulo.

MUSIC: Out

Ian: In 1979, agent Bill Shopperle worked out his system for monitoring the entrance to 98 Prince with the 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 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 Underboss: The Rise and Fall of a Mafia Family," written by two former Globe reporters, Gerard O'Neill and Dick Lehr. To a large extent, I'll 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.

Ian Coss: How did you get into 98 Prince Street?

John Gill: Picked the lock.

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

John Gill: Actually, it was a very cheap lock. probably the cheapest lock you could put on. It was a builder's grade, uh, lock, no alarms.

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

John Gill: Yeah, I was. I was. I was shocked. Um, 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.

MUSIC: Enter

Ian: By the judge's order, the FBI team had 30 days to place 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.

MUSIC: Post

Ian: The fourth attempt was on a Sunday night. The temperature had stayed below freezing for days and no one was out on the street.

John Gill: Everything was quiet

Ian: This time, the agents had also tailed Angiulo and some of his key lieutenants, to make sure no one would be in the building. At around 2 am 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.

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

Ian: That was the voices they were hearing: talk radio.

John Gill: W E E I.

MUSIC: Out

Ian Coss: Could you describe the inside of 98 Prince Street?

John Gill: It was almost like a clubhouse. You know, they had a big dining room table, and the back was a, uh, it was almost a commercial kitchen, gigantic stove. cook a buffalo back there.

Ian: Other than the 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 Angiulo usually sat.

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

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

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

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

John Gill: A wire that was supposed to be, uh, ground was hot and a wire that was supposed to be hot was ground and, uh, we just didn't want to take the chance.

Ian: 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.

John Gill: we decided to leave it alone and go with the battery.

Ian: Gill 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.

MUSIC: Enter

Ian: 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.

John Gill: Pick up any wire clippings, get out of there.

Ian: Before they left, the case agent, Ed Quinn, noticed a plaque on the wall over a 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.

MUSIC: Out

Ian: Gennaro Angiulo rose to power out of an era of instability and violence.

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

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

Ernie DiNisco: What the Italians did was sit back and, when things got dull, they would go out and commit a murder

Ian Coss: hmm.

Ernie DiNisco: other side would, uh, retaliate.

Ian: Ernie DiNisco is a longtime federal prosecutor, including on the Angiulo case.

Ernie DiNisco: This went on. And if I'm not mistaken, I think there was 63 gangland murder cases from the late fifties into the early sixties.

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

ARCHIVAL: To the survivors went a multi million dollar network of illegal businesses and control over Boston's loan sharking and gambling operations.

Ian: There are actually two important figures who emerged out of this era, and would dominate Boston's crime world in the decades to come.

ARCHIVAL: …...this empire of illegal activity is...gennaro J. Angiulo.

Ian: The first of course is Gennaro Angiulo, 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 Nickolson. But back then, Bulger was just known as Jimmy, and he a rising leader of one of the old Irish Gangs, Winter Hill.

Ian Coss: What was Jimmy Bulger's relationship with Jerry Angiulo like?

Kevin Weeks: They had a working relationship. they didn't have a trusting relationship.

Ian: 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 Angiulo were clearly rivals. They both had gambling operations, with Angiulo in the North End, and Bulger in South Boston. Weeks describes it as a delicate truce.

Kevin Weeks: Jerry and them had never faced anyone like Winter Hill, you know, they had a lot of guys and they were all shooters.

Ian Coss: Winter Hill did?

Kevin Weeks: Winter Hill did. Yeah they were all killers. So it was, you know, everybody got along. No one wanted a war.

Ian: 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 them information about Angiulo. 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 Angiulo at 98 Prince St, 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 floorplan of the Angiulo's 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 Bulger was making his move.

Ian Coss: What did he look like when he got mad?

Kevin Weeks: there's two phases of mad. Mad, he get mad at the average person and stuff, no big thing. But then when he got really mad at someone, you know, his eyes, I mean, he had blue eyes and, uh, they turned red, all red around them, kind of his lip would curl up and his voice would get a little lower and soft, deep. And, uh, you know, there was a problem.

MUSIC: Transition

BREAK

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

Bill Shopperle: No.

Ian: Bill Shopperle, the camera guy.

Bill Shopperle: Uh, I had an idea it'd be a couple of months, but of course, they weren't getting good evidence. Jerry wasn't talking to anyone really.

MUSIC: Enter

Ian: 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 four pm, Gennaro Angiulo himself would arrive in a red 2-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 quieted the room to watch, of all things, WGBH channel 2 -- public television.

MUSIC: Out

Ian: Apparently, the mafia leader was a great fan of "The Wild, Wild World of Animals" -- with its stories of sly and ruthless creatures.

ARCHIVAL: who's have more clearly proven themselves a menace to man than the African crocodile.

Ian: The FBI could also hear the brothers watching Celtics games.

ARCHIVAL: Bird. Bird again. Bill Walton,

Ian: 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.

Bill Shopperle: So they kept getting approval to extend the bug.

MUSIC: Enter

Ian: 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.

Bill Shopperle: We needed six Sears batteries to run the whole system.

Ian: Six car batteries essentially, to power that camera set-up, and they 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 the other car, waiting to pull right in. That became Shopperle'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.

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

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

Bill Shopperle: It was like a cherry bomb going off.

Ian: The battery blew up in his face.

Bill Shopperle: I had never made that mistake again. And of course that woke you up.

John Gill: I remember him, work on all those batteries and he was running around with jeans with holes in them from the battery acid.

Ian: John Gill, the audio guy.

John Gill: He worked his butt off, but he never slept at night.

MUSIC: Out

Ian: The batteries for the audio bug also had to be swapped out, three times over the whole operation. That meant the whole routine of unlocking the door, going into 98 Prince and going up above the ceiling panels.

Every time the agents went in there was a chance of being seen, and they waited eagerly to hear if the daily activity continued as normal.

John Gill: We picked up on the wire that they, uh, suspected they might be, uh, there might be something there. And, uh, I went over there to, 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 they, if they were looking, they weren't looking in the right places. Okay. I didn't see any roof panels being pulled or walls being torn down, so I was happy.

Ian: And eventually, things started to pick up. This is audio from the bug, recorded at 98 Prince St.

ARCHIVAL: If you fuck someone that's close to us, I'm going to give you a shake now. So you get some of this shit.

Ian: 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 ya down, never get up unless he's gonna kill ya."

Angiulo would often punctuate these pronouncements with the line: "you understand American?"

Ian: 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 loansharking -- all the makings of a RICO case were there. And then one night, an even bigger charge: murder, ordered by Angiulo himself. Quote: "Meet him tonight. I hope it's tonight. Just hit him in the fuckin' head and stab him, okay? The jeopardy is just a little too much for me. You understand American? OK let's go."

MUSIC: Enter

Ian: 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

Ian Coss: Was it weird going in there in broad daylight? After having been in there surreptitiously so many times?

John Gill: Oh, very much so, yeah. We could see what color everything was.

Ian: John Gill went in that day as part of the technical team. They found a safe upstairs in 98 Prince St, wedged into a fireplace.

John Gill: and we beat it up with a sledgehammer, and we had a locksmith come in and drill it.

Ian: 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 Angiulos were still doing alright.

MUSIC: Transition

Ian: 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 Angiulo's misfortune, while listening to the mafia boss boast on the tapes, and deride Whitey Bulger -- convinced of his own invincibility.

ARCHIVAL: Whitey up the

Ian: Apparently, Morris got so drunk that Bulger had to drive the FBI agent home in his own government car.

Ian: 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.

ARCHIVAL: Around 9 o'clock, the back room here at Francesca's is cleared out and a white tablecloth is set with silver and china. Jerry Angiulo 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.

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

MUSIC: Out

ARCHIVAL: The, uh, Subject, three of them were arrested at Francisca's, Francesca's restaurant

Ian: The U.S. Attorney's Office announced the arrests the next day at a press conference.

ARCHIVAL: I think, I think you can answer that. They refused to be fingerprinted and ..Photographed.

Ian: They also announced the charges and all the defendants.

ARCHIVAL: Including Gennaro Angiullo, Victoria Niccolo Angiullo, Donato Angiullo, Samuel

Ian: 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: RICO.

ARCHIVAL: Title 18 United States Code, Section 1961 4, that is, a group individuals associated, in fact, which engaged in various criminal activities

Ernie DiNisco: at this point in time, it was the 1st case that dealt with an entire crime family like that. We, this was the 1st 1.

Ian: Ernie DiNisco was one of three prosecutors on the case.

Ernie DiNisco: 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.

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

Ian: Angiulo'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 Angiulo 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 DiNisco recalls, Angiulo’s lawyers went in pretty confident too, because by this time they had heard the tapes from 98 Prince St, with the garbled shouting and constant radio noise. And they had told Angiulo: no one can understand these tapes.

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

Ian: The prosecutors knew this was a problem too.

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

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

Ian: 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 these transcripts.

Ernie DiNisco: 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

MUSIC: Enter

Ernie DiNisco: And this was, uh, this was brand new. No one had really done this before.

Ian: 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.

Ian: The hearing went on for weeks, tape after tape after tape.

Ian: With the court appointed magistrate listening to every one on a pair of headphones.

ARCHIVAL: Johnny came off in his car, you know,

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

Ian: DiNisco remembers on one of the key tapes, the one where Jerry Angiulo ordered the murder, the voices were just barely barely audible.

Ernie DiNisco: And they had a Western, a Western movie on what there was a cattle drive or something, and you could hear the cows in the background mooing.

Ian: Now all DiNisco could do was watch the magistrate with his headphones on, and hope the magistrate heard what he heard.

Ernie DiNisco: 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.

Ian: The transcripts were ultimately allowed. And not only could the magistrate understand the tapes, Jerry Angiulo could understand them too.

Ernie DiNisco: And he was following along. and he knew that, um, they were in deep trouble at that point in time.

MUSIC: Out

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

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

MUSIC: Enter

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

Ian: testimony continued for eight months. There were occasional outbursts from Angiulo at the defense table, but mostly he just sat there, silent, his chin sticking forward. DiNisco recalls one day a group of elementary school students came to observe the trial, sitting right behind Angiulo.

Ernie DiNisco: And he turns to the kids and he says, remember kids, crime doesn't pay unless it's organized

MUSIC: Post

Ian Coss: So he never, he never lost his big mouth and his swagger, even through the trial.

Ernie DiNisco: no. No.

MUSIC: Shift

Ian: In February of 1986, five years after the bug was placed in 98 Prince St, 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 DiNisco: And then we resigned. I've got to say that it was not a lot of, um, personal outbreaks and, uh, you know, I'll cry from them. And They were strong about it.

Ian: In a final flourish, Gennaro instructed his brothers to march out of the courtroom in lockstep, like an army platoon. He was sixty-six 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.

MUSIC: Out

Ian: 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.

Ian Coss: 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 DiNisco: I think that that that's correct. That's a, that's a valid assumption.

Ian: Gennaro Angiulo 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 Angiulo 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."

MUSIC: Enter

Ian: There is 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.

Or as Kevin Weeks put it:

Kevin Weeks: It's the same old story. You know, the government sees money to be made, they get involved in it, you know, they're the biggest gang in the country.

Ian: 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. Genarro 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 any more. It was part of the community in a way that no state lottery could ever be.

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

Ian Coss: 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.

MUSIC: Transition

Ian: 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.

ARCHIVAL: For too long, the label of Taxachusetts has driven established industry and business from our state.

Ian: Here in "Taxachusetts," a tax revolt was under way, and the lottery offered a way out.

ARCHIVAL: Don't you resent it when out of state friends kid you about living in Taxachusetts?

Ian: That's next time.

The series is produced by Isabel Hibbard and myself, Ian Coss. It’s edited by Lacy Roberts. The editorial supervisor is Jenifer McKim with support from Ryan Alderman. Mei Lei is the project manager, and the Executive Producer is Devin Maverick Robins.

I just want to recognize again the book The Underboss by Gerard O’Neil and Dick Lehr. 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 Vorhees, 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 Mamie-Hawa Bawoh (Mah-mee How-wah Bah-woh - like whoa, slow down). Our closing song is “You Made Me Love You,” performed by Massachusetts State Treasurer Bob Crane.

Scratch and Win is a production of GBH News and distributed by PRX.