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Ex-Wiseguy Henry Hill Always Had 'A Ringside Table'

Hill (left, with Ray Liotta, who played him in the movie GoodFellas) was the central figure in Wiseguy, the 1986 Nicholas Pileggi book that later became the Martin Scorsese-directed film. (WireImage)

Henry Hill, the mobster-turned-informant portrayed by Ray Liotta in the film Goodfellas, died Tuesday at age 69. Hill's colorful life — he lived in Cincinnati; Omaha; Butte, Mont.; Independence, Ky.; and Topanga, Calif., among other places — was documented in crime reporter Nicholas Pileggi's 1986 book Wiseguy and then in Martin Scorsese's film Goodfellas, which was based on Pileggi's book.

In 1986, Pileggi joined Fresh Air's Terry Gross for an in-depth conversation about Hill, who was a member of the Luchese organized-crime family before deciding to become an informant. His subsequent testimony led to dozens of convictions and forced Hill to enter the witness protection program.

Hill's criminal record while in witness protection led to his expulsion from the program in the early 1990s. In recent years, he lived openly in Topanga, Calif. with his fiancée Lisa Caserta.


Highlights From Pileggi's 1986 Interview:

On Henry Hill's stature in organized crime

"He was a middle-level hustler. He was one of the guys in an organized crime group. His job was to hustle money. He was what they call an earner. He was hyperactive. According to his mother, he never stopped. He would run through the house, slam doors. He took care of rabbits, he ran across the street and washed windows. If he ate, he was jumping up and down while he ate. ...

"When he wound up in criminal activities, he was working just as industriously. He was working on three, four, six, a dozen things at the same time. He would have a loan-shark operation going, he was doing booking, he would have a phony restaurant, he was running guns, he was planning hijackings, he was also divvying up the money in different situations, all at the same time. And flying up to Boston every couple of weeks to fix and bribe Boston College ballplayers in a point-shaving scam. He never stopped."

On how Henry got into the mob

"Henry just fell in love with wiseguys. He told me, 'I'd look out my window — and there was a mob hangout — and see these guys get out of their cars and they had these great big coats.' And that's what he talked about — these great big coats. And they'd show up there and they always had a lot of money and jewelry and diamonds. And they were shown such great deference in the neighborhood."

On Hill's relationship with his wife

"We all know couples where we wonder, 'Why does she stay with him and why does he stay with her?' We all know that the one of those people is not as good as the one we like. But we'll never know the answers to those things. One of the things that was interesting in Karen's case was that she found him thrilling for whatever reason. I'm sure there are a lot of other women who would have found him disgusting. But she, for whatever wiring she had, she found him thrilling. He turned her on. He was an exciting guy.

"She tried to explain it to me. She said, 'He could go places. He had money. He was an action guy. There I was, going out with little schmendricks. They were going to be accountants. If we were lucky, we'd go to Chinese food in the mall. With Henry, I would go to the Copa. And I would have a ringside table. And people always looked and me and thought, 'Who is she?'"

On how Henry dealt with his frequent prison sentences

"There are religious furloughs where you go out for religious training. It allows you to get out of the program and have contact with your family. ... Henry sees this and he says, 'Get me a religious guy.' So they got a phony rabbi to write the letter to the prison. The prison is very responsive to religious letters. All of a sudden, Henry is now going off on 'religious studies' on weekends.

"He got Jimmy Burke to pick him up, they'd cross Pennsylvania, go to Atlantic City, he'd belly up to the craps table and shoot craps until his ankles swolled. And that's what he would do for his whole religious weekend. Then get back in the car Sunday night and drive back to the prison. At the same time, his wife would fly down from New York and other wiseguys would come down — and their weekends in prison were spent in Atlantic City."

On the $5.8 million Lufthansa heist of 1978

"It was the largest successful cash robbery in American history. It was a cargo handler out at Lufthansa who owed a bookmaker who worked for Henry Hill about $80,000 from debts. This is a poor cargo handler who had a poor, junkie habit as a gambler. To get the wiseguys off his back, he knew about this money being transported to this country from Europe. And he told them about it. They went and held the place up and they got it.

"It was so much money that instead of it freeing the group — there were about a dozen men — when every man began asking for his share, they began disappearing. Or they would wind up dead. And the other guys weren't sure why they were dead. You don't know, because everybody's in so many other things. Henry knew. He said, 'I sensed it. I knew Jimmy. I knew what they were up to. And I knew when you asked for your money, you're dead.'

"About 10 people who were involved intimately with that robbery were all murdered. Henry was one of the last and one of the ones not to be murdered. And when he was arrested in the drug case, he realized that his days were over. Even if Henry didn't talk, they were going to kill him because he might have talked. And that's when he turned as a government witness."

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Transcript

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. Henry Hill, the mobster made famous in Martin Scorsese's 1990 film "Goodfellas," died on Tuesday after a series of health problems. He was 69. Here's a scene from the film with Ray Liotta as Henry Hill.

(SOUNDBITE OF MOVIE, "GOODFELLAS")

RAY LIOTTA: (As Henry Hill) By the time I grew up, there was 30 billion a year in cargo moving through Idlewild Airport, and believe me, we tried to steal every bit of it. So you gotta understand, we grew up near the airport. It belonged to Paulie, and we had friends and relatives who worked all over the place, and they would tip us off about what was coming in and what was moving out.

(As Henry Hill) If any of the truckers or airlines gave us any trouble, Paulie had his union people scare them with a strike. It was beautiful. That was an even bigger moneymaker than numbers, and Jimmy was in charge of it all. Whenever we needed money, we'd rob the airport. To us, it was better than Citibank.

GROSS: The screenplay for "Goodfellas" was adapted from the book "Wiseguy" by Nicholas Pileggi, who co-wrote the screenplay with Martin Scorsese. "Wiseguy" reveals how organized crime worked on the street level in the '60s and '70s. Hill's crimes included truck hijackings, drug dealing, extortion and gun running. In 1978, Hill was part of the largest single robbery of its time, a $5.8 million cash and jewelry theft at JFK Airport, which became known as the Lufthansa heist.

Hill claimed he never murdered anyone, but he admitted being present during many murders and knew where the bodies were buried. I dug a lot of holes, he told the Stanford Advocate in 2010. Fearing for his own life, after many of the other men who participated in the Lufthansa robbery were murdered by the heist ringleader, Henry Hill cut a deal with the government and entered the witness protection program in exchange for his testimony in cases brought against his former criminal associates.

Hill was expelled from the witness protection program in 1987 for drug possession and other misbehavior. By then, many of the criminal associates Hill had informed on had either died or were in prison. And he managed to keep up a bit of his celebrity in recent years with appearances on "The Howard Stern Show" and other talk shows.

Pileggi's book "Wiseguy" is based on interviews he conducted with Hill while Hill was in the witness protection program. Pileggi is a journalist who had covered organized crime since 1956. "Wiseguy" focused on the life of a mid-level hustler in the mob, not a big shot, but ironically Pileggi's book and movie turned Hill into a big shot.

A 25th anniversary edition of the book "Wiseguy" was published last September. Here's how Pileggi described Hill when I spoke with Pileggi in 1986, shortly after "Wiseguy" was published.

NICHOLAS PILEGGI: He was one of the guys in an organized crime group. They have different jobs. His job was to hustle money. He was what they call an earner. He was a great guy at hustling money. He was hyperactive. According to his mother, he never stopped. He was totally active as a youngster.

He would run through the house, slam doors, took care of rabbits, ran across the street and washed windows. He never stopped. If he ate, he was jumping up and down while he ate, obviously in need of some kind of assistance, maybe a bucket full of thorazine, but no matter how it worked out, he - that kind of activity and energy has always been with him.

When he wound up in criminal activities, he was working just as industriously in those areas. And so he was working on three, four, six, a dozen things at the same time. He would have a loan-shark operation going. He was doing book-making. He had have a phony restaurant. He was running guns. He was in heroin and cocaine. He was planning hijackings. He was doing hijackings. He was also divvying up the money in different situations, all at the same time, and flying up to Boston every couple of weeks to be able to fix and bribe Boston College ballplayers in a point-shaving scam. He never stopped.

GROSS: It's interesting how he got into organized crime because he wasn't born into it. It's not that his parents were involved with crime, and he grew up in it. He got it through basically a job when he was a kid.

PILEGGI: It was just the opposite. His family were hardworking people. His father was Irish, an Irish immigrant, actually, an electrical worker in the construction industry and a hardworking man his whole life. His mother was a Sicilian woman, a hardworking woman from a hardworking family their whole lives. They were not gangsters. There were not part of any organized crime world.

And he had lots of brothers and sisters. None of them have ever been involved in organized crime. Same house, same families, good providing parents. I mean they weren't wealthy people, but there was always food in that house, and the children never, never were hungry and never were not nicely clothed nor educated.

Henry just fell in love with wiseguys. He told me, he said: I was just a kid, and I would look out my window. And there was a cabstand across from where he lived, and it was a mob hangout. And he said: I'd see these guys get out of their cars, and they had these great big coats. And that's what he talked about, their great big coats.

And they'd show up there, and they always had a lot of money and jewelry and diamonds. And they were shown such great deference in the neighborhood. It should be said that Henry grew up in the Brownsville East New York section of Brooklyn, which was the home of Murder, Incorporated. It was a neighborhood in New York that is famous for producing gangsters.

What West Point is to generals, East New York, Brownsville is to organized crime and to the mob. They just came from there. And they occupied a position in a working class, hardworking neighborhood. They were the people with the power. They looked - it looked as though it worked. And to gullible kids like Henry, they looked up to the racketeers, and in the end that's what he wanted to be.

GROSS: How did Henry get in, into that circle?

PILEGGI: Well, after school - he noticed they had the cabstand across the street, and every once in a while there would be a kid helping, going and get coffee, going and get beer and that sort of stuff. And Henry asked his parents if he could get an after-school job, and his mother and father were both delighted with the idea.

After all, he's a highly active kid. There were a lot of kids at home. The cabstand was right across the street. How bad could it be? And he went over there, and of course he just fell in love with that world. And he went over to start running errands, and he was great. Wiseguys loved him. He was cute. He was smart. He was a shrewd little kid, and he hustled.

He would go - if they wanted him to get coffee, he'd go and he'd get that coffee back before it was cool. And if they asked him to clean their cars, they'd give him a dollar to clean the car, he'd clean it and polish it, and they'd never had their cars cleaned and polished so beautifully.

And they realized the kid was a worker. He was really hustling with them. And at one point they said, one of the guys said, Henry, come here. He went over. See this envelope? Take this envelope to the pizza joint around the corner on (unintelligible) Avenue. Around the corner he went. It was a numbers - it was records from the numbers game, and before you know it, by the time he was 12, he was hustling numbers. He was running the numbers. He was running errands, past plainclothesmen.

He began spotting plainclothesmen. He could spot at cop at 13. He knew who they were. He had all their license plates memorized. He was doing better with the numbers than he was in school.

GROSS: When he was arrested the first time, because he was found using a stolen credit card, there was this big initiation party afterwards, like he'd lost his virginity, and...

PILEGGI: Well, that's what they said. And now that, you know, that is the kind of thing if you write about it, some people think: Well, then, after their first arrest, there is this ritualistic party where they all get together.

(LAUGHTER)

PILEGGI: That wasn't what it was at all. It was just a sort of spontaneous, happy experience for all of these guys, because all of these wiseguys have all been arrested, and Henry hadn't been arrested. He was 16 years old. He got arrested for some stolen credit cards. He called his gangster pals. They said don't worry about it, Henry, you go to court and we'll bring Copout Louie, the lawyer, in, copped him out.

And it was this extraordinary happy experience. It was as though he had graduated.

GROSS: We're talking about the 1950s here, right? What - you had talked about how Henry, when he was a kid, really looked up to the mobsters in the neighborhood, and the mobsters had a lot of control over the neighborhood. What about the, you know, law-abiding, neighborhood citizens? How did they treat the hoods in the neighborhood and the big-time mobsters who lived there?

PILEGGI: With deference, because they were fearful. If you didn't have to have anything to do with them, you were a happy man in those neighborhoods. You walked to work, you came home after work, you carried your lunch to work, and you carried your pail back, and you went into your house, and you kept your door closed, and you had nothing to do with them. If you had nothing to do with them, you were safe, you were immune.

If, unfortunately, you had to borrow money from them, if unfortunately you wound up working in a place that they owned, you were involved, and your life wasn't your own.

GROSS: One of the ways that he really came into his own as far as his work in crime is when he got into the Army. You talk about all the little schemes he organized when he was in the Army, selling things.

PILEGGI: Yeah. He's Sergeant Bilko. That's who he is. And even before he went into the Army, you've got to remember, he was cashing counterfeit twenties. He figured out, or one of the guys told him how to soak a counterfeit 20 in coffee grounds and a little bit of water overnight, and then it looks like an old bill in the morning.

He would cash those things. He was running the numbers. He had gotten a phony job in a construction union they had gotten for him, then he split the check with the wiseguys. Now he gets into the Army, and you would think, well, what's he going to do in the Army.

Well, he said he loved the Army. It was like going away to camp. He had never learned to swim. He had never seen trees. He had never done any of those things. And here he was learning how to swim. It was the fresh air fun camp for Henry Hill.

And then on top of that, it was a place you could make a lot of money. I couldn't believe it, he said. You know what they do in the Army? He said: They buy the same amount of meat and cook the same amount of steaks on the weekends that they do during the week, only on the weekends you maybe have 10 soldiers in a camp instead of 250 because everybody's on weekend furlough. And he said, and there were all these steaks. They would cook them every weekend and throw them out. And he said that was crazy.

So what I did, he said - he stole all the steaks on the weekends and sold them to the local restaurants. He gave the chef or whoever was in charge of the kitchen a few bucks, and he pocketed the rest. Now that he's got some money, he realized soldiers are always broke. Come payday, they need money. So he would lend them six for five. He had a little loan-sharking operation going on. And he said it was (technical difficulties) at the end of the pay line on payday, and as they came down the line, they'd pay me back the money.

GROSS: With that experience, he came home - and when he got home, he started doing the kind of operations that we all vaguely know about, but we don't really know how they work. Like we know that there's all these truck heists and hot goods. So you found out how these truck heists are organized.

PILEGGI: It was fascinating. I mean, it was just a revelation to me. I had no idea how it - I mean, we all know about hijackings, but I had no idea they were hijackings to order, number one, and number two, there's a whole scale of things that you prefer to hijack.

I would think - for instance, what would you - if you had your chance of hijacking a truck, what would you do? Well, somebody would say, well, I'd just hijack a truck full of $15,000 Rolex watches or something, you know, something really expensive. That's not it at all. Henry said the most valuable thing in the world to hijack is a trailer truck full of lobster and shrimp.

I said what? He said absolutely. He said they go like that. And he said we have all these restaurants, we know these guys. These are - now, we're talking about legitimate, ostensibly legitimate, restaurant owners in New York City, in the New York City area, who will buy a trailer truck full of lobster and shrimp so quickly. And he said they just buy the truck, they'll buy a quarter of a truck, they'll buy an eighth of a truck, a tenth of a truck, half a truck, whatever they need. And he said and by dinner the evidence has been eaten. There's no evidence left. Everybody's been eating it. They just cooked it right then.

The other thing they liked to steal were razorblades. They would steal these little packs of clip-on razorblades that people used. And the reason for their value is that they're so small and so expensive and so many and so easy to distribute and no serial numbers, and they sell them off to ostensibly legitimate businessmen, guys who might have a little discount store here, a guy who might have a little wholesale business that supplies lots of drug stores, and that's where they would unload the stuff.

So one of the revelations I had was that they don't operate in a vacuum. They don't steal a truckload of lobster and then go park on the corner of 17th Street and Walnut or something and say: Psst, would you come over - do you want to buy a lobster? Do you want to buy a frozen lobster? There's no way of doing that. They actually steal the stuff and then pass it on to ostensibly legitimate businessmen. They work in cahoots.

The second thing that is fascinating is the way they knew what to steal. And it turns out they have friends and contacts and pals, and people who owe them money, guys who are deeply in debt to gambling, guys who are deeply in debt to their bookmakers, have to serve as spotters. These are men who might work in an airport, they might work on the piers, they might work on the docks. They're in loading areas, they're in invoice areas, and they can spot the trucks. They can spot what's there, and they can tip the wiseguys off, and they get a piece.

They don't get a lot, but what they do is they can bring down their debt a little bit. It guarantees they're not going to get their kneecaps broken, and it's a way of surviving for them.

GROSS: Now, some of the truck drivers are in on it too, and they know they're going to be hijacked, and they play right along with it. How does that work?

PILEGGI: Well, there's not much they can do. I mean, the truck driver knows that this truck - he's driving out of there with a truckload full of razorblades or shrimp or color televisions, and he's been given the signal. He knows that something's going to happen. And something does. He's along the road, and all of a sudden two wiseguys are there at a red light, and he just gets out.

He knows. He gets out, and he gets into a tail car, they usually tail the truck to make sure there isn't a police car following, and he gets into the tail truck, and they'll take him to a motel. Quite often they'll have some coffee. They'll take his wallet, and they'll take his license plate - his driver's license. They'll know where he lives and they'll know his name. And they'll say: If you remember what we look like, we know who you are, and we know you have a family, and you'll be sorry.

And so when the police arrive, they're not very cooperative. Well, I don't know, he'll say. The guy was - you know, he's seven feet tall and he had green hair. I mean they'll give a description that is totally opposite of what the men were, and they're safe. There's no way - the wiseguys, that is, they're safe. They're gone. They've stolen the stuff, they've moved it into loading platforms and docks.

That was the other thing. They have warehouses that are honest warehouses, not a mob warehouse with a mafia flag on the roof. It's a real warehouse where the truck next to it, the truck on either side of it is unloading legitimate goods. But their truck, their little bay where they're unloading crooked goods, nobody knows.

Things are not stamped this load is crooked, these men are gangsters. But the guy who runs the crew, the hijacking gang, they know a guy who sort of maybe runs that warehouse or those loading platforms, and he gets a little bit too.

So the money, the profits, are divided among legitimate people, quasi-legitimate people, who allow them to use their facilities to get these stolen goods into the mainstream of the American process.

GROSS: Now, did the union play any part in this?

PILEGGI: Yeah, at Kennedy Airport. One of the big complaints of the FBI and a lot of other people is that when the - say the airline says, wait a minute, every time this guy works, we lose a truck, a valuable truck, and last time we sent out two trucks, and we switch-swapped everything so that nobody would know unless he was really this guy, and it turns out he knew, and they stole the right truck. He is the spotter. We know he's the spotter. We're going to fire him.

Well, if he is a member of a local that's organized crime, the organized crime shop steward, the guy who is working in that union, will go to the employer and say you can't fire him. He's a union member. You can't prove it. You can't prove anything. If you fire him, we're going to have a wildcat strike. So the employers quite often have to hire them back, or they'll take them out of that area and put them someplace where they don't - they can't spot that well. And that's what they have to do.

But they know the guy is a spotter, and they can't touch him because the union will cause a problem for the trucker.

GROSS: We're listening back to an interview with Nicholas Pileggi, recorded in 1986, after the publication of his book "Wiseguy," about the life of Henry Hill. Hill died Tuesday. More after a break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: Let's get back to the interview I recorded in 1986 with journalist Nicholas Pileggi about his book "Wiseguy." It's about the life of smalltime mobster Henry Hill. Pileggi and Martin Scorsese adapted "Wiseguy" into the film "Goodfellas." Hill died Tuesday at the age of 69.

Now, another thing that a lot of us suspect, but we don't really know how it works, is that sometimes when cars are stolen, they're really going to be resold by organized crime. And he actually had a scam like that.

PILEGGI: Oh yeah. He had a - he was a very close friend of somebody who was extremely powerful and influential in Haiti, of all places. And what they would do is they would give kids $100 to steal cars. They would leave these cars on - in parking lots, and then every once in a while they would get all the cars together, they would get special invoices, bills of lading.

The cars would be sent down with new - everything was forged, and there were people taking care of them on the dock. It was all put on boats, shipped to Haiti, and the money, the profits from those cars were kept in Haiti, and then Henry would fly down every once in a while and get his money.

GROSS: Could you tell how much of an alliance he and his cohorts had with the police?

PILEGGI: Well, obviously not all police, but there was a - it was obvious, and he has spoken about it, the fact that lots of cops - not lots, but many cops were on the take during his rise. He said that you had cops who you knew, and they would take care of you, and you would take care of them.

For instance, when they were - and they were well-known. You know, these guys were known to the cops. The cops knew who every one of these guys were, some of these guys. And some of them would give them a tough time, and others wouldn't.

But he talked lots of times about getting in brawls. When they were going around trying to create paper locals or create locals within good unions, to try to take over the union or take over the local, they were forever getting in brawls on picket lines and stuff.

The cops would come and break it up, and they would throw them in a car, and the other guys would get arrested, they'd be thrown in the car, and Henry said they never took us to the precinct. They'd drive us three or four blocks away and then tell us to get out. And the cops - those cops were taken care of.

GROSS: Was he during all this period aligned with a larger New York family?

PILEGGI: Oh yes, he was - he was associated - his mentor was a man by the name of Paul Vario, who was a capo in the Lucchese crime family, Lucchese crime family, named after Thomas Lucchese, Three-Finger Brown, one of the five large organized crime families in New York City.

GROSS: So what did he owe to the family? He wasn't very big in the family, but he was...

PILEGGI: He's a worker. I mean, that's who they are. They're all workers. There aren't a lot of bosses. They're just - everybody's a worker. And he was an earner, and he made a lot of money. He earned a lot of money for them. And he would pay tribute to his boss, who was Paul Vario.

If he ever made a score - for instance when they took $480,000 from Air France, when they stole 480,000, the first thing he did was go and give $60,000 of it, 60,000 to Paul Vario. Paul didn't even know they were doing the robbery. He didn't have to know. Henry was out there hustling. You are on your own.

It works quite differently than we sometimes - or than we have been led to believe by the movies and by often the FBI. They're really franchises. They're like franchisees. That's what it is. And only if they have a problem and a dispute among themselves do they take it to the next level.

And then those men on the next level act as the judges in those disputes.

GROSS: But if it turns out that he did a heist and didn't pay tribute, I guess that's when he'd really be in big trouble.

PILEGGI: Then he's in trouble, and - or if he decided to stick up a card game or to stick up a place that was associated with the families. Most of the murders, or so many of the murders that he talked about in the book came about because young guys, tough young guys with guns thought that they could go and stick up card games and stick up crap games that were run by organized crime families.

And these young guys were often the sons of mob chiefs and mob bosses and mob lieutenants and capos. And the kid would go and do the robbery, and he would get away with it once, twice, three times. Then the bosses would go and talk to his father: Will you stop your kid? He's going to get in trouble. We don't want to do things, but if he keeps this up, he's going to - and the fathers would go and talk to their sons and say, are you crazy, you can't do that. Go to another neighborhood. Stick up another card game. And the kids would go anyway, and eventually those kids were murdered. And they - when Henry talked about it, he says, if they liked the father, and they knew the family, they knew the father, they would always shoot the kid in the heart.

I said, why? He said: That way his face was OK for the funeral, so they could have an open casket.

GROSS: Oh gosh.

PILEGGI: I mean, that was a sign of respect for his father: They wouldn't shoot the man's son in the face.

GROSS: Nicholas Pileggi recorded in 1986, after the publication of his book "Wiseguy," about Henry Hill. Hill died Tuesday at the age of 69. We'll hear more of that interview in the second half of the show. A 25th anniversary edition of the book was published in September. Pileggi and Martin Scorsese adapted "Wiseguy" into the film "Goodfellas." I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross. We're hearing about the life of Henry Hill, the New York mobster whose life was the basis of Martin Scorsese's 1990 film "Goodfellas." Hill died Tuesday, at the age of 69. More than any other mob figure in the late 20th century, Hill changed both the perception and the reality of mafia life in America, according to George Anastasia, the Philadelphia Inquirer's longtime organized crime reporter. He says Hill's life laid bare the treachery and deceit that was at the core of the underworld.

Let's get back to the interview I recorded with journalist Nicholas Pileggi in 1986, after the publication of his book about Hill, "Wiseguy." Pileggi and Scorsese adapted the book into the screenplay for "Goodfellas." "Wiseguy" used Hill's life to examine organized crime through the life of a small-time guy, not a big shot.

I found his relationship to his wife really interesting. When she married him, she had no idea that he was involved with the mafia. When she found out, she didn't leave or anything. I guess it didn't bother her that much.

PILEGGI: No. Well, I mean we all know - I suppose we all know couples where we wonder: Why does she stay with him, and why does he stay with her? We all know that the other - one of those people is not as good as the one we like, right. But we'll never know the answers to those things.

One of the things that was interesting in Karen's case is that she found him thrilling, for whatever reason. I'm sure there are a lot of other women who would have found him disgusting. But she, for whatever wiring she had between her ears, she found him thrilling. He turned her on. He was an exciting guy.

And she tried to explain it to me. She said, well, you know, I mean, he could go places. He had money. He was an action guy, and there I was going out with little schmendricks. They were going to go and they were going to learn if they got - if they were really smart, they were going to be accountants, and I saw the rest of my life with nothing. I mean, maybe if we were lucky, we'd go to Chinese food in the mall. I mean, when Henry - she said, I would go to the Copacabana. And when I got to Copa, I had a ringside table. And people always looked at me, and they thought: Oh, my. Who is she? And it was thrilling to her. She was turned on by that.

In addition, Henry was a tough piece of work. He's a good-looking guy. He certainly was when he was younger. And he was sort of - he's a dashing guy, and he was funny and he was humorous, and he - his pals were sort of noisy, funny guys. They were the center of attraction always, wherever they went. And they always have a lot of money, and they were always treated very, very well.

GROSS: He had a mistress, eventually. And the impression I got was that Friday nights, all the guys took out their mistresses, and Saturday nights, they take out the wives.

PILEGGI: Smart impression. That's absolutely right. Friday night is the girlfriends. That's girlfriend night. They call it gumada night. But that's - it's girlfriend night. The reason for that is Friday night, they're still making money, circulating, running around. And so you pick up somebody during the week, or you get your girlfriend on Friday night and you run around. Now, Saturday comes, that's the night to stay at home with the family, right - as much as they do stay home with their families. They're not at all as - you know, the ones that I've been writing about and found out about - are not that devoted. They're not out there working on the grape arbor. But Saturday night is usually the night when all of the guys go out with their wives. And they try not to - and never to mix it up.

GROSS: So the wives won't see the girlfriends.

PILEGGI: So the wives don't see the girlfriends, and the girlfriends don't see the wives. And there's no, you know, that's - I mean, to the girlfriends, the wives, oh, these terrible people. I don't know. Someday I'll leave her, you know. And to the wives, they don't even know about the girlfriends - or not supposed to know.

GROSS: He eventually got sentenced to 10 years in prison. But even in prison, he was able to do all this hustling. Before he even got into prison, he'd figured out ways of decreasing his sentence. What was his scheme for that?

PILEGGI: Well, he had so many. But, you see, that's it. A wiseguy is a wiseguy is a wiseguy. They never stop. When they - he was convicted of extortion and a whole bunch of wiseguy stuff, and federal prison, got 10 years. I said, wow, 10 years. He seemed too young to have spent 10 years in a federal prison. And it turns out, he spent about four-and-a-half of those 10 years in prison.

Well, the first thing he tells you is, listen, if you're convicted, you get six days off a month for every six. And if you take this course and go to a continuation school, you get three weeks off every year of your sentence. And if you - and by the time he had figured all the schemes out, all the sincere rehabilitation programs that all of the penologists, all the sociologists, all of the people studying this had worked so hard and industriously to get rammed through the legislature so that people in prisons could rehabilitate themselves, wiseguys take those programs and distort them for their own purposes. So Henry not only was out in four-and-a-half years, but long before he got out, Henry was already into every furlough program, every notion of anything.

There are religious furloughs where you go away for a weekend of religious training - a very sane, a very sober thing. It allows you to get out of the prison and re-acclimate yourself to the communities that you are going to be entering. We don't want people out of our prisons going right back into them. It allows you to perhaps have contacts with family and children, to be able to reacquaint your family with you. It's a sane, very intelligent, sociologically studied course. Henry, of course, sees this, and he says, great. Get me a religious guy. So they got some phony guy who was a phony rabbi to write the letter to the prison. The prison is very responsive to religious letters. All of a sudden, Henry is now going off on religious studies on weekends.

He gets in an Oldsmobile on a Friday afternoon. He even got Jimmy Burke to go on Jewish religious studies with them, if you can believe it. And they go off to Atlantic City, is where they went. They'd get in a big Oldsmobile and drive lickety-split, cross Pennsylvania to Atlantic City, where Henry said he, you know, he'd just get up to the crap table, belly up to the crap table and shoot craps until his ankles swoll(ph). And that's what he would do for his whole religious weekend. Get back in the car Saturday and Sunday night, and drive back to the prison. At the same time, his wife would fly down from New York. Other guys, wiseguys would come down, and their weekends in prison were spent in Atlantic City.

GROSS: When he got to prison, there was actually a little welcoming committee there to meet him. What kind of inside connections did he have as soon as he got there?

PILEGGI: Well, that's the other thing, if you're a wiseguy, if crime is your life and people who are in crime are your closest friends, you're also going to know everybody who's in prison. This is a continuing saga that goes on, and it's all of your guys are in prison at one time or another. So when it's your turn to go to prison, you're all going to know guys in prison, and they will have already paid off the crooked guards to make life cushy for them. And now you take their role and you pay off the crooked guards and continue this operation.

The stranger who gets arrested and convicted and goes to prison who knows no one, who doesn't know how to pay off anybody, who doesn't even dare to try to pay off anybody, they're the people who do the tough time. When Henry got there, he was greeted by a bunch of cronies right there, right at the door. They then went, took him through the orientation period, and within two weeks, he was living in a dormitory setting outside the wall.

Now, Lewisburg is a maximum security prison. A Warner Brothers wall is around the thing, with these turrets and guys with guns. And there was Henry, outside the wall in a dormitory setting, something like a Holiday Inn, with four wiseguys in each room. He was in there with three other hoods. They had stakes. They had beer. They had wine. They had liquor. They had Anisette after dinner. They had their own little coffee grinders. They had - it was an extraordinary thing. And the guards, who should have been reporting this, of course, didn't. It cost them $500 a week in bribery alone.

GROSS: And, in order to make that money, he started selling drugs in prison.

PILEGGI: You got it. He started selling drugs in prison. He started bookmaking in prison. He started loan-sharking in prison. He started doing everything he ever did.

GROSS: How did he get the drugs in to sell them?

PILEGGI: They were all smuggled into him by other organized crime people, including his wife smuggled drugs in for a while. She would put the drugs into a - she went out and got an oversize brassiere and hip boots - or, you know, high knee boots several sizes too large - and she began stuffing the drugs into those boots. The search, when you go in for your visits, are very cursory. There's no major thing. You go through a - the kind of metal detector that you have in the airport, but that's all they do. And they get to know these women week after week after week, and you could just walk in with it. There's no major effort to keep it from being in.

GROSS: When he got out, he still was selling drugs...

PILEGGI: Mm-hmm.

GROSS: ...and that wasn't - that was still taboo in parts of organized crime.

PILEGGI: It was. It was in his crew, in his organized crime - the family he was associated with, namely the Paul Vario faction of the Lucchese family. Paul Vario just hated drugs, didn't want them anywhere around him, didn't want anyone dealing drugs near him.

He knew - I don't know whether it was a moral issue or was it ethical or was just business, but Henry told me that Paul Vario would - you were forbidden to dealing drugs if you were with him. The reason Vario said was that drugs were corrupters. Drugs not only - he said, you wind up in drugs, you're going to wind up having a cop for a partner. There's so much corruption in the operation, you'll wind up with cops for partners, and I don't want to be near you. It's a world of total betrayal.

If the world of the Henry Hills and the wiseguys and organized crime is filled with betrayal, the world of the drug dealers is betrayal in - to the 10th power. They are - there is no one there that isn't - who isn't squealing on someone else all the time. And I think Vario was worried about that. And so he felt they had enough going with gambling and with loan sharking and with racketeers of all kind, that he didn't need the drug money. He was doing very nicely, thank you.

Unfortunately for Vario, the guys under him - the Henry Hills, the Anthony Stabiles, the Angelo Sepes, those guys - they weren't doing as well as Paul Vario. They weren't doing as well as their superiors. And so for them, the extra money and the - they could get from drugs was extraordinary, and they went into drugs, and they kept it. They had to hide not only from the cops, but they had to hide from the organized crime bosses.

GROSS: Did the bosses find out?

PILEGGI: On occasion they did, and on occasion, you'd find dead people. They literally kill people. If they were caught in drugs, they would be killed.

GROSS: It seems that after Henry Hill got out of prison, he got much more ambitious and took on some really bigger jobs than the jobs he'd taken on before.

PILEGGI: Well, he did. He came out prison - one thing he told me, he said, you know, I'd never smoked a marijuana cigarette until I went to prison. He said I learned about drugs in prison. He said I never did anything. He said, I was around. I did a lot of bad things, but I never was into drugs. But in prison, the only way he could get money to pay off the guards was to smuggle drugs into the prison. People wanted pot. People wanted coke. And so we got into the drug world while under the aegis of the United States Bureau of Prisons. When he got out, he found that it was one of the only ways he had available to him to make a lot of money quickly.

GROSS: We're listening to an interview with Nicholas Pileggi recorded in 1986, after the publication of his book "Wiseguy," about the life of mobster Henry Hill. The book was adapted into the film "Goodfellas." Hill died Tuesday at the age of 69.

More after a break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: We're listening to an interview with Nicholas Pileggi recorded in 1986, after the publication of his book "Wiseguy," about the life of mobster Henry Hill. The book was adapted into the film "Goodfellas." Hill died Tuesday at the age of 69. Hill's crimes included truck hijackings, drug dealing, extortion and point shaving.

The point shaving scheme that he cooked up really shook college basketball. That was a pretty big story.

PILEGGI: Oh, it was.

GROSS: One of the players was sentenced to 10 years, was it?

PILEGGI: Yes, yes, one of them was. He'd come out of prison, and one of the men who was selling drugs for him in prison, or was smuggling the drugs into him at this point, was - lived in Pittsburgh. The guy owed him $15,000. Henry was going to take that money and go back into operation. When he got to the guy's house to pick up the money - now Henry isn't out of jail 24 hours, he's going to pick up his $15,000. The guy said I don't have any money. All I've got is a garage full of grass - marijuana.

Henry said, what am I going to do with that? He said, well, you know, take it. Take a couple of suitcases. Go get a suitcase. Get it. I'll give you all you want. That'll be $15,000 worth. You'll be amazed. It'll be easy to get rid of. He said what am I going to do? Henry had to get some kind of money. So he gets the suitcase full of dope, and then gets on a Greyhound bus and goes back to New York. He was afraid to take the plane, because he didn't know what - whether anybody would be able to spot the grass, whether a dog would sniff it. He didn't know anything about drugs on the outside at that point.

When he got back to New York, he's got this suitcase full of grass. He can't go to Paul Vario and his usual crime people and say, listen, I've got a suitcase full of grass. They would've ostracized him, killed him, beaten him up. Who knows? So we had to go behind their back and find other crime people who were dealing in drugs. And he managed to unload the suitcase. He got something like $25,000. It was some special stuff. And he said oh, boy. This is great. What am I knocking myself out for? And from then on, drugs became a major - first grass, then he went into chemicals, and then into cocaine and to heroin. Drugs became a major source of revenue for him.

At the same time he was dealing the drugs, he's talking to this guy in Pittsburgh who was the supplier and he said, you know, I know this guy, grew up with him. He used to be a ballplayer, and in fact, now he's a ballplayer at Boston College. You know, he's a shrewd guy. And he said, well, maybe we can reach him. Maybe we can reach him.

And there was a meeting, and Henry said, listen. I'm a sports fan. You're a sports fan. You're a college guy, rah, rah, rah. Look, I am not asking you to throw a game. That's the last thing. I don't believe in that. But you don't have to win by so much. I mean, we've got a point spread of six, you win, you don't win by six. That way I can bet the game and I win, and you win the game because you win the game. You just don't win by so much, and I will bet on the number.

And he managed - according to the federal court where trials took place and people were convicted - to convince one of the players, and then that player convinced a couple of other players to shave points. And the point-shaving scandal at Boston College was a result of that.

GROSS: And then the other really big heist he did was he was one of the people behind the Lufthansa heist...

PILEGGI: Yes.

GROSS: ...in which they got $5 million, was it?

PILEGGI: Five-point-eight-million dollars in cash, not a penny ever recovered: the largest success cash robbery in American history.

GROSS: And this was through getting the cargo from a plane. It was...

PILEGGI: Again - yes. Again, it was one of these cargo handlers out at Lufthansa who owed a bookmaker who worked for Henry Hill about $80,000 from debts. This is a poor cargo handler who had a junkie habit as a gambler. He used to bet $500 on a game on a $300-a-week salary check. And he, to get the wise guys off his back, to get that debt absolved, he knew about this money being transported to this country from Europe, and he told them about it. They went and they held the place up, and they got it.

GROSS: That's when things started falling apart for him.

PILEGGI: It did. It was so much money. It was such an unbelievable amount of money, that instead of it freeing the group - and there were about a dozen men involved in that - when every one of the men began asking for his share, they began disappearing, or they would wind up dead. And the other guys were never sure why they were dead.

You don't know, because everybody's in so many other things, and if one guy died, the rumor would get around, well, you know, it was a dirty - a drug deal. He had a drug in Newark that really went down bad, and they had to whack him, and he's whacked. Nobody knew why everybody was disappearing. Nobody wanted to relate it to the fact that we were getting murdered whenever we asked for our money.

Henry knew. Henry said, I sensed it. I knew it. I knew these guys. I knew Jimmy. I knew what they were up to, and I knew when you asked for your money, you're dead. And that's what happened. About 10 people, 10 of the participants, 10 of the guys who were involved intimately with that robbery - who actually went in with the guns and held the place up - were all murdered.

Henry was one of the last not to be murdered, and when he was arrested in the drug case, he realized his days on the street were over. Even if Henry didn't talk - you remember, he was convicted of 10 years, never talked. Never did anything. Even if he didn't talk, they were going to kill him because he might have talked. And that was it for Henry, and that's when he turned as a government witness.

GROSS: So what were his choices? He could've spent a lot of time in prison. Do you think they would've gotten him in prison?

PILEGGI: Oh, he would've never - I mean, he never would've gotten to prison. They would've killed him only on the possibility that he might have talked. That would have been enough to sign his death warrant. They knew he was vulnerable, and being vulnerable is all you have to be. Then you're dead.

GROSS: So it was shortly after that that he contacted you to write the book, because...

PILEGGI: Well, no. He contacted the United States Attorney's office and was in the program. When I met him, he was already a witness, a federal witness.

GROSS: Part of why he wanted to have this book written is so that he could, through a percentage of the royalties, get enough money to pay his lawyer. Have you ever thought that maybe he really embellished his life a lot so that he could...

PILEGGI: Oh, that was one of my first thoughts when I...

GROSS: ...help you do a best-seller?

PILEGGI: Yeah. Well, that was one of my first thoughts when I had to deal with him. But what the book is, it's - while it's got Henry's story, everything he's told me, he was also telling the FBI at the same time. He was being debriefed for all of these cases at the same time. These cases went to trial. He testified in these cases.

In these cases, if he would have lied in any one of these cases, he would've committed perjury. The entire agreement with the United States government would null and void. He would go back as a convict, and he would've been dead. So it was in his interest to keep telling the truth to the FBI, and I found out exactly what it was he was telling them.

And then I would ask him other questions. In addition, there were affidavits. There were separate court statements. There were court documents. There were tape recordings made when he didn't even know he was going to get arrested. And there were also people he knew who I was able to gain access to. In addition, I, of course, talked to members of his family. I got to his wife. I talked to his kids. I talked to his mother. I talked to guys he grew up with.

So it was pretty well-covered. I mean, I've been doing this too long to get - to spend three-and-a-half years on a fairytale. I mean, that wasn't what I was after. And the kinds of things he came up were so revealing, so different than I had assumed, and it was just - you couldn't make it up. In other words, you couldn't make up - the stories he told me, I could not make up if I was sitting in Malibu writing for the movies.

GROSS: I love something you said to me before. You said that when you heard him talk about his life in organized crime, it sounded like the Kramdens. It sounded like "The Honeymooners" more than it sounded like "The Godfather."

PILEGGI: Yes. That's - and that is what it is. And it turns out, even the bosses on that - on his level, his immediate bosses, and even the big bosses, they are not these totally sophisticated Robert Duvall, Al Pacino brilliant people. They are really working-class people for the most part with very little education, and, you know, these people hang around together.

They don't have any friends outside of their immediate world. And every crew - Henry's little crew with Jimmy and Marty and Anthony and all these guys, that's the crew. And their wives all hang around together. And when - and if - by some miracle, to go to vacation somewhere, they all go together. It's like this little bloc of people, because they can't trust anyone else.

And they don't move outside of their little worlds. They're very parochial, very narrow. We're not talking about Al Pacino traveling to the Dominican Republic or to Brazil for the weekend with Kathleen Turner. I mean, we're talking about really working class, hard guys from a - a low-income socioeconomic world, even though they make a lot of money.

GROSS: I really never heard the term wise guy used to describe a gangster until your book.

PILEGGI: Yeah. I never heard it, or, I mean, never thought of it as a term, but that's what they use to call each other. There was this - hanging around, they'll say, what do you do? Oh, you know, he's a wise guy. He's all right. He's a wise guy. They used that term. They don't say I'm a racketeer or I'm a gangster. They say, no, I'm a wise guy. He's a wise guy.

GROSS: Nicholas Pileggi, recording in 1986 after the publication of his book "Wise Guy" about the life of Henry Hill. Pileggi and Martin Scorsese adapted the book into the film "Goodfellas." Hill died Tuesday at the age of 69. A 25th anniversary edition of "Wise Guy" was published in September. Coming up, critic Lloyd Schwartz talks about "Car 54 Where Are You?" The classic TV sitcom has been released on DVD for the first time. This is FRESH AIR. Transcript provided by NPR, Copyright NPR.

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