Criminal - Uncle Harold

Episode Date: June 27, 2025

In 1997, Eric Konigsberg received a strange voicemail from someone in prison — a hit man who had confessed to at least ten murders. Eric and the man had never spoken before, but Eric had a hunch about who it was: his uncle. Eric Konigsberg’s book is Blood Relation. Say hello on Facebook, Instagram and TikTok. Sign up for our occasional newsletter. Follow the show and review us on Apple Podcasts. Sign up for Criminal Plus to get behind-the-scenes bonus episodes of Criminal, ad-free listening of all of our shows, special merch deals, and more. We also make This is Love and Phoebe Reads a Mystery. Artwork by Julienne Alexander. Check out our online shop. Episode transcripts are posted on our website. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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A very wise person once told me, once you turn certain levers on, you can't turn them back off. And I don't need to right now. Like everything's working. I don't need to give more of my personal life. That's This Week on Channels, wherever you listen to your favorite podcast. This episode contains language that might not be suitable for everybody. Please use discretion. Tell me about the first time you ever learned about your uncle being a hitman. The first time I ever heard of my uncle and the first time I heard that this person existed or heard his name actually was in boarding school in Connecticut.

I was writing for the school paper and I was interviewing a buildings and grounds worker at the school who had once been a policeman in New York. This is Eric Konigsberg. He asked about my name. He said there was a knock-around guy, mafia figure, Harold Konigsberg. He said, where are you from? I said Omaha, Nebraska. He said, he was from Bayonne, New Jersey. I said, my father grew up in Bayonne, New Jersey.

Eric assumed it was a coincidence. I did not call my father, but I mentioned it to some classmates. At boarding school, I thought it would be kind of funny. I think I wanted to brag about it. And I got blank stares from them, and I never mentioned it again for 10 years. Eric Konigsberg finished school and went on to get a job as a reporter. And then one day, his uncle came up again.

A detective he was interviewing for a story about the mafia asked Eric if he was related to the famous Konigsberg, the mafia hitman. This time, Eric called his father. And he said, that's my uncle Heshy. Heshy was, you know, a Yiddish nickname for Harold. And my father said something that really surprised me. He said, please tell me you said you weren't related. He said, why would you want your name, our family name,

attached to someone like that? And he told me to drop the assignment and never write about the mafia. And it was so surprising to hear my father use an expression, an important sounding expression like our family name. Eric had always been close with his father. He dropped the story about the mob and didn't go looking for his uncle. But then, two years later, Uncle Harold came looking for him.

I'm Phoebe Judge, This is Criminal. You received a voicemail, an odd voicemail in 1997. What did it say? It said, well, I'm not going to give you a message. Tomorrow's another day. If you're home between 8 and 8.30, you'll get a surprise. I'll call you, we'll talk, we'll have a nice conversation. And I'm telling you, it's a very, very interesting conversation, Mr. Connigsburg, and you'll

have something to talk to your father and your brother about. After he said, I'm telling you, it's a very interesting conversation, Mr. Connigsburg, he said, that's your name, ain't it? Okay, kid, take care and God bless. And it was this coarse accent, you know, a real outer burrow accent. But I had a hunch who it was. When he called back a couple of nights later, he asked Eric to come visit him in prison. Eric decided he needed to know more, that he'd try to write about his uncle.

That point, I'd already spent my entire adult life writing about other people and quite a bit about crime stories. And the thought that I had a story in my own family tree, you know, that was very exciting. Even non-journalistically, it was kind of a thrill to think that I had this notorious criminal in my family. I grew up in a very bourgeois, normal family. And I think I got kind of a perverse thrill from this at first. Before Eric went to visit his uncle Harold in prison, he tried to find out more.

He started asking his family about him. He was said to have weighed 13 pounds at birth. And his sisters talked about his beautiful blonde hair. He had these blonde ringlets that his mother did not cut until he was three years old, and then she saved them in a canvas bag in their living room. And one of my great-aunts, Aunt Ruthie, said, it was like Samson, except the minute they cut the hair, he became the devil. Eric's family told him that as a child, Harold got into fights with other kids.

He got in trouble at school. He once scared a handyman who was working at their house that as a child, Harold got into fights with other kids. He got in trouble at school. He once scared a handyman who was working at their house by shaking a ladder he was standing on. When the handyman yelled at Harold to stop because he could fall, Harold said, I want you to fall. And when Harold was 10 years old,

he threw a rope around the cat's neck and hung it from a steam shovel that was in the family's yard. As a teenager, Harold took up boxing and earned the nickname K.O. for knockout. And he started working with an influential gangster named Abner Zwilman. By the time Harold was in his early 20s, he'd been arrested several times for things like robbery and assault. And then in 1950, when Harold was 22, he got his longest prison sentence yet. He got a 14-year sentence for robbing an appliance store at gunpoint and severely beating its

owner. Harold served about eight years of his 14-year sentence before being released. When he got out, all of a sudden he was a major mafia figure. He was not a member of any of the five mafia families of New York, but he worked for apparently four of the five regularly, and also there was a sixth of family in New Jersey, the DeCalvocante family. He also worked for them. Harold's name, the Connigsburg name, was often in the newspapers.

Harold's parents' home was once searched by police. And his brother-in-law, Louis, was arrested when the police mistakenly thought he was involved with Harold in a murder plot. Louis was quickly released from custody, but his arrest made the papers. Meanwhile, Eric's grandfather, Leo Konigsberg, ran a successful business in Bayeux, New Jersey, delivering butter and eggs. My grandfather, the butter and egg man, he was obsessed with his reputation his entire life. And then I realized, well, this was why.

And my grandmother said as much. You know, he couldn't do anything wrong. He couldn't accept a cup of coffee on the house at a diner from a client he was delivering food to for fear that people would say, you know, he played a little dirty or he wasn't to be trusted or had mob connections because of his brother. Eric spoke to other people who had known his uncle Harold, journalists who had covered him, lawyers who represented him, law enforcement who had investigated him.

People described him with superlatives. They described him as the smartest hitman and the toughest Jew they ever saw. He was at once incredibly brutal and incredibly seductive. One of Harold's lawyers told Eric, quote, he was my first true sociopath and brilliant, brilliant. He'd remember any detail about you, where you'd gone to school, how you met your wife, where you shopped.

And he was cherubic, almost like a precocious child who wants your approval. You wanted to tell him, good for you, you make me so proud. My grandmother said, stay away from him,

because once you go, he will never leave you alone. And I could tell it was upsetting. But you still went. Yeah. Yeah. It didn't feel entirely real, the damage that he had done to others and the pain for my family and embarrassment or fear that he would somehow overtake their lives or mine,

but he still could even after decades away in prison. I thought great story. We'll be right back. Support for Criminal comes from Quince. Quince is known for their classic lightweight clothes that feel and look like they're from luxury brands, but come at an affordable price. It's a great place to look for clothes you'll be excited to wear in the heat this summer. They have 100% linen shorts and dresses that cost just $30, and they sell swimwear and leather sandals too. I just ordered two new European linen shirt dresses from Quince for the summer.

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And he said, I'm here to find a co-founder and a wife. This week on The Gray Area, is AI changing the college experience? Listen to The Gray Area with me, Sean Illing. New episodes every Monday, available everywhere. Almost a year after Harold left that first voicemail, Eric went to visit him at Auburn Correctional Facility, a maximum security prison near Syracuse, New York.

There was a visitor's room, and I waited there, and a heavy steel door opened, and in walked my Uncle Harold. And at first, you know, it was really strange because he looked like my grandfather with this long, wavy white hair and this very gentle looking face. He was, I think, 74 by then and, know seemed older and I remember I put out my hand to shake his hand and he said what the fuck kind of way is that to greet family and he gave me a kiss on the mouth. And what did you talk about?

He wanted to talk a lot about our family. He wanted to know what people said about him. He wanted, obviously, to find a way to reconnect and be acknowledged or even be admired or loved or at least get on people's minds. Harold had two daughters, who he still spoke to, but the rest of his family had mostly cut ties in the late 1950s when his mafia involvement got to be too much. I could tell that he was very lonely and it was very sad, this old man in prison, unable to even get his family to take his calls.

Tell me, what was his personality? What was he like? He was nasty. He was coarse and mean and had a short temper. I might ask something and he'd say, why do you ask stupid questions? Or I'd say, he'd tell me something surprising, I'd say really, and he'd say, yeah, really, what the fuck's wrong with you? He liked to quiz me about things, see how much I knew about him. He could also be kind, and he would remember details about me.

He was incredibly persuasive when he wanted to be. He thought he could persuade me to write something fictional about him, change the details, and we would sell it to the movies. He said we could sell it to those Weinstein brothers at Miramar. Eric visited Harold nine times that year. For a while it went well, and then it didn't go well,

and he was obstreperous and sometimes helpful and sometimes not helpful. And I started dreading going to visit him. Eric told us that conversations with Harold weren't really a back and forth, but more like being on the receiving end of a, quote, steady stream of invective, insult, and curses, and that Harold could be needy and manipulative. After a year of visits, Eric decided to take a break from seeing his uncle, but he kept working on the story.

And for two years, you know, I went and interviewed hundreds of people, more than a hundred. And I found, you know, thousands and thousands of pages of sealed documents, and I found people whose lives had been upended by his, and he started to feel a lot more real. By the early 1960s, the FBI had begun surveilling Harold Conigsberg. He had six offices, three in New York and three in New Jersey. And I found hundreds and hundreds of pages

of sealed FBI reports where they had surveillance on these offices and you could see the details of what he was doing and some of the stuff is really high end and some of it's really low end. The distribution of stolen watches and clocks and a single fur piece, but also the purchase of B-25 and B-26 bombers, possibly to sell them to Cuba, as well as a deal to sell arms to Cuban revolutionaries. He became a bookmaker and a loan shark.

He claimed as a loan shark to have a million dollars on the street at any given time. On top of all of this, Harold was also a hitman. He was a contract killer. I once said something about him being hired by the mob, and he snapped at me and he said, he said, punks get hired. He felt that he was in charge of his own enterprise. Sometimes he would work for more than one mafia family at

the same time or working for two families that were at war with each other. Sometimes he worked for the Teamsters. Teamsters were a coalition of trucking unions who represented, you know, the truckers for better pay and working conditions. And they were very influential politically because if they endorsed a candidate, they could deliver a lot of votes. The crime that Harold Conningsburg was serving time for when Eric went to visit was a murder

he'd committed in 1961 for a Teamsters leader named Tony Provenzano. At the time, in the 50s and 60s, the Teamsters union was deeply entangled with the Italian mafia. This was the era of Jimmy Hoffa, the Teamsters president who once said, these organized crime figures are the people you should know if you're going to avoid having anyone interfere with your strike. One of the things the mob got out of the alliance was loans from the Teamsters pension fund, which served as a sort of bank for the mafia.

They used the money to build casinos in Las Vegas. Jimmy Hoffa was the general president of the Teamsters, but there were also the leaders of all the local chapters. These local leaders could rally their members to, for example, vote for a politician who would then owe the mob a favor. Tony Provenzano was president of one of these local teamsters chapters in Union City, New Jersey. Tony Pro was running for re-election of the local 560, and he was being opposed by a very

popular sort of rival named Anthony Castellito, and was afraid he was going to lose his bid for re-election. So he asked Harold to kill Castellito. Harold and a man named Salvatore Bergoglio, or Sally Bugs, went to Anthony Castellito's house. They knew Castellito would be on his way home from a meeting, and they expected to be led inside by his 27-year-old son, Anthony Jr., who they were also planning on killing. These two guys, it was Harold and Sally Buggs, showed up and they claimed to be FBI agents.

Anthony Jr. let them inside. But Castolito's wife and teenage daughter were also home. There were mafia codes against killing women and children, so the plan was off. Before they left, they sat down in the living room with the family and said they could be reached at the Newark FBI office. Castellino's son said he could tell something was funny about the two visitors. He thought it was strange that Sally Buggs was wearing argyle socks and little pointy loafers. He said no FBI agent would dress like that.

Harold and Sally Buggs eventually left. They made a new plan. They would murder Castellito at his country home in upstate New York. On June 5, 1961, when Anthony Castellito arrived at his home in the country, Harold and Sally Buggs were there, hiding. As soon as he walked in, Sally Buggs struck him on the head with a piece of lead-filled hose.

He was knocked down, but not knocked out, and he fought back. So my Uncle Harold walked to the porch and ripped a length of Venetian blind cord off the porch, drew it around Castellito's neck, and garreted him. When they were finished, they got rid of Castellito's body. His family had no idea where he was or what had happened to him. Harold had been offered $15,000 for his role in the murder, though it's unclear if he was ever paid the full amount. Sally Buggs was given a position with the Teamsters, which Tony Provenzano announced

at a union meeting. Anthony Castellito's son, Anthony Jr., was at that meeting. He was also a Teamster. And he recognized Sally Buggs as the guy who had shown up at his home looking for his father and claiming to be an FBI agent. He still didn't know where his father was or that he'd been killed.

It all seemed suspicious, so he contacted the authorities, but nothing came of it. And did it seem like they had gotten away with it? They were immediate suspects, and they were questioned by state police right away. They had an alibi. The police searched the property and found nothing, and the case was left unsolved for, you know, for decades. We'll be right back. for, you know, for decades.

We'll be right back. What do President Biden's two senior most national security advisors think of the U.S. strikes on Iran? The longer tail of the threat from Iran remains and will have to be taken seriously. I'm Preet Bharara and this week, Jake Sullivan and John Feiner join me on my podcast, Stay Tuned with Preet to discuss the US military action in Iran and what comes next for the Middle East. The episode is out now. Search and follow Stay Tuned with Preet wherever you get your podcasts. 2025 marks 50 years since a trailblazer named Jam Todd decided to go to the gym with her little boyfriend. I had started going with Terry to the gym just because, you know, he's your cute boyfriend and you love him and you like you want to spend all your time together.

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and inspire other women to lift weights. More recently, millions of women have started, but why now? Answers on Today explained, every weekday in your feet. A couple of years after the murder of Anthony Castellito, Harold was back in jail in Hudson County, New Jersey for a different crime, extortion. And he was somehow able to buy off the warden. Anthony Castellito, Author, The New York Times, Author, The New York Times Harold somehow was living in the warden's office.

And actually, my father remembered that the one time he had gone to visit his uncle Harold, he had visited him there. And he wondered why they visited him in the warden's office. But Harold was basically living there as a sort of private apartment. I talked to another inmate there who said he had his own TV, a telephone, a radio, a fridge, a hot plate, a desk, and a sofa. And the prisoner even remembered a wine-colored rug and parlor chairs. He sent the guards out for pizzas. It was said that he sometimes left with the warden to go to the racetrack together.

LESLIE KENDRICK-ROSENZWEIG Corruption may have been rampant at the Hudson County jail, but outside, things were changing. A nationwide crime syndicate known to its members as Cosa Nostra and to others as the mafia or black hand are explored by John L. McClellan's Senate investigation subcommittee. Attorney General Robert F. Kennedy is the first witness. Robert F. Kennedy was taking on the mob. In 1961, when he became attorney general, there were 73 convictions of people involved in organized crime.

By 1964, there were nearly 600. Meanwhile, J. Edgar Hoover and the FBI were cultivating more sources in the mafia. And in 1965, they got word from a prison official that Harold Connigsberg was interested in meeting with them, quote, alone, as soon as possible. He was facing two serious sets of charges for two big extortion cases, one in New York and one in Philadelphia. And he realized that the best way to preserve himself, to keep putting off being tried,

he offered to talk to FBI agents as an informant. — The FBI agent who met with him wrote in a memo to J. Edgar Hoover that Harold was, quote, down and out. The hoods that he did so much for are abandoning him and giving him a hard time. And he wants to have the last say. When he offered to be an FBI informant, what he was offering them was a chance to try to pursue Tony Pro.

Tony Pro was a big target of Bobby Kennedy's at that point. Harold was promised immunity if he could lead the authorities to the body of Anthony Castellito, the man he'd murdered for Tony Provenzano. In June of 1966, he accompanied a group of marshals to a piece of New Jersey farmland where he'd remembered burying Castellito. The marshals searched for two days and found nothing. The investigation moved very slowly for almost a decade, until finally in 1978, both Harold Conningsburg and Tony Provenzano were tried and eventually convicted of murdering Anthony Castellito.

Harold's own confession to the FBI was ruled inadmissible at trial, but the prosecution had enough to convict him without it. Both Tony Provenzano and Harold Connigsberg received life sentences for the Castellito killing. But the Castellito family still didn't have a body to bury. Anthony Jr. told Eric, quote, You tell your uncle he didn't just kill this guy, he destroyed a whole family. The murder of Anthony Castellito was the only one Harold was ever convicted of. In the end, how many murders did Harold confess to? He confessed to at least 10. He gave the FBI information on 20. In 10 of them, he described

himself as the actual murderer, and in others, he was vague. The FBI felt pretty certain that he had committed all of them. By 2001, Eric had finished a draft of his story for The New Yorker. In the previous two years, he'd read hundreds of pages of FBI documents and spent time with some of the victims of Harold's crimes. But he hadn't been back to visit his uncle. My editor said, you have to go back there one more time to let him know the piece is coming out.

And this was the funny thing. He said, see if he'll cooperate with the magazine's fact-checking department. And I really didn't want to go. But I flew up there, and I waited for him, and I walked in. And he said, go and get me a Dr. Pepper. So I did. And he was, he was, he was get me a Dr. Pepper. So I did. And he was scratchy from the beginning. He wanted to know why I hadn't been back in two years.

He wanted to know what I wanted. And I said, this magazine story I've been working on is going to go to press in a week or two. And without missing a beat, he took off his reading glasses and he said, the day something that has my name in it and your name on it hits the street, you are dead. He said, I'm going to kill you. I'm going to chop you up a hundred different ways. And you can put that in your fucking magazine. And then he asked me to go to the vending machines and get him some microwavable popcorn and some orange soda.

I sat there with him for a couple hours and it just kept going on and on and on, telling me all the different ways he was going to kill me and why I deserved it. So finally I gave up and I walked out. Did you actually believe that he had the power, still had the power to somehow connect with someone on the outside to do this hit? Yeah, that's a great question because I had no idea. How would I know?

And I remember I told my father all of this and I said, yeah, but what do I do? And he said, call Grandma. Everyone listens to her. So we had to come up with a plan to get my grandmother to get Harold on the phone, all these decades of, after decades of not speaking to him. Eric told us he felt naive. His grandmother had warned him not to get involved with Harold. My grandmother said, I wish you hadn't gone and done this, but nobody threatens my grandson.

So she said she would take care of it. And I told a friend of mine, I remember, and she said, so Granny's going to call off the hit? Ultimately, nothing ever came of his threats. A few weeks went by and then months, and I started to think that if he really was going to kill me, he'd have done it already. But you know, it scared the hell out of me. Do you ever regret going to see him taking on this project? Oh no, no.

I enjoyed learning about the complexity and even the upsetting parts of my family history. In many ways, it brought me closer to my father's family, who we had always been kind of aloof from. It made me admire my grandfather and grandmother tremendously. The fact that they had lived and built a career and built a life and raised a family in the same town, in the same community where my uncle was bringing great shame on all of them. In his book, Eric writes, the funny thing about blood is you can't control how you feel about your relatives.

Even after I had seen what Harold had done to others, I was unable to hate him quite as deeply as I wanted to, or even as much as I felt I should." But Eric also writes that he thinks he would have had an easier time forgiving a stranger rather than family. Quote, I was a lot less capable of wishing him any possibility of redemption. He spent seven years researching Harold, and eventually says the project stopped being

about understanding his uncle or finding the humanity in him. Eric became more interested in documenting what happened and who his uncle had hurt. It was actually really meaningful for me to bear witness to what he had done and to track down all the relatives of so many of his victims. I became very fond of and got to know Castellito's son and his wife quite well and to see, you know, to take the measure of my uncle's impact on their lives. LARISSA Harold was paroled in 2012. He moved to Florida, where he eventually ended up in an assisted living facility. The New York Daily News interviewed some of his fellow residents, and one woman said, quote, He doesn't look like a mobster. He's just cranky.

He died in 2014. ah The Nadia Wilson is our senior producer. Katie Bishop is our supervising producer. Criminal is created by Lauren Spohr and me. Nadia Wilson is our senior producer. Katie Bishop is our supervising producer. Our producers are Susanna Robertson, Jackie Zagico, Lily Clark, Lena Sillison, Megan Kinean, and Katie Mingle. Our show is mixed and engineered by Veronica Simonetti. Julian Alexander makes original illustrations for each episode of Criminal.

You can see them at thisiscriminal.com. And you can sign up for our newsletter at thisiscriminal.com slash newsletter. Eric Konigsberg's book about his uncle is called Blood Relation. We hope you'll consider supporting our work by joining our membership program, Criminal Plus. You can listen to Criminal, This is Love, and Phoebe reads a mystery without any ads. Plus you'll get bonus episodes. These are special episodes with me and Criminal co-creator Lauren Spore talking about everything

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