Saturday, August 23, 1958, Idle Wild Airport, New York. At 3:47 p.m., a Pan American Airways flight took off for Havana, Cuba. Among the passengers was Herbert “Herby” Goldstein, 42, a certified public accountant and, for the past seven years, Bumpy Johnson’s personal financial manager.
Herby carried two suitcases. One contained clothes. The other contained $2 million in cash, money he had systematically embezzled from Bumpy’s operations over the previous six months through a sophisticated scheme of falsified ledgers, phantom expenses, and redirected payments. Herby had been planning this heist for three years, studying every detail, creating multiple backup accounts, and establishing connections in Cuba, where he could disappear into Havana’s expat community and live comfortably for the rest of his life on stolen money. He timed his departure.
Perfectly. Saturday afternoon, when Bumpy would normally be spending time with his family and wouldn’t be reviewing financial documents. By the time Bumpy discovered the theft, which Herby estimated would take at least 72 hours, Herby would be safely in Cuba, beyond the reach of U.S. law enforcement and, according to him, beyond the reach of Bumpy Johnson’s organization.
He was catastrophically wrong. Because what Herby didn’t know, what he couldn’t have anticipated despite years of careful planning, was that Bumpy Johnson had suspected financial irregularities for two months and had been closely monitoring Herby’s activities, waiting for him to make a move. The moment Herby’s plane took off at 3:47 p.m.,
Bumpy received a phone call. By 4:15 p.m., Bumpy’s organization had identified Herby’s destination, contacted associates in Havana, and initiated a response. By 5:47 p.m., exactly two hours after Herby’s plane left New York, Herbert Goldstein was dead in a Havana hotel room. His body was being prepared for shipment back to New York in a coffin with a note pinned to his chest.
Stole $2 million at 3:47 pm. Dead at 5:47 pm. 2 hours. Nobody steals from Bumpy Johnson. BJ. To understand what happened on August 23rd and why the response was so quick, so efficient, and so decisive, you need to understand the relationship between Bumpy Johnson and Herbert Goldstein. They had worked together since 1951.
Herby was one of the few white professionals willing to handle the finances of a Black gangster in 1950s America. Most legitimate accountants wouldn’t touch Bumpy’s business. Too risky, too criminal, too dangerous. But Herby was different. He was smart, discreet, and greedy. He saw opportunity where others saw danger. Bumpy paid him exceptionally well—$50,000 a year, equivalent to roughly $500,000 today—to manage the complex financial operations of a multimillion-dollar criminal empire.
Number games, heroin distribution, real estate, legitimate businesses used for money laundering, “protection” schemes. All of it generated cash that had to be recorded, laundered, invested, and hidden from federal authorities. Herby handled it brilliantly. For seven years, he was the perfect accountant.
Meticulous, reliable, trustworthy—or so Bumpy thought. But in early 1958, Herby began to have ideas, dangerous ideas. He had been managing millions of dollars for years and taking home $50,000 a year. He saw the money flowing through Bumpy’s operations, conservatively estimated at $5 million a year in revenue, and thought, “Why am I only getting 1%?”
Why do I do all the hard work while Bumpy gets everything? I’m the one who makes this organization work financially. I deserve more.” Those thoughts festered inside, grew, evolved into a plan. Herby couldn’t demand more money. Bumpy would see that as greed, disloyalty, suspicion, but he could take it, steal it, quietly, carefully over time, accumulate enough to disappear, start over somewhere Bumpy couldn’t reach him.
Cuba was perfect. Havana in 1958 was a haven for American expatriates, criminals, and gamblers. The Batista government was corrupt and welcomed anyone with money; there was no extradition treaty with the United States, and there was limited cooperation with U.S. law enforcement. Once Herby was in Cuba, with 2 million, he would be untouchable, safe, and free.
He started stealing in February 1958. Small amounts at first: 10,000 here, 15,000 there. Phantom expenses, inflated costs, money disappearing into accounts Herby controlled. He was careful, professional, covering his tracks meticulously. But by June 1958, Bumpy noticed irregularities. Nothing obvious, nothing he could prove, just anomalies: numbers that didn’t quite add up, expenses that seemed high, income that seemed low.
Bumpy wasn’t a trained accountant, but he’d been running criminal operations for 30 years and had developed a knack for knowing when something was amiss. He called a meeting with Herby in late June. “Herby, I need you to explain some numbers to me. These expenses here, $47,000 for operating costs in May. Break it down for me. What exactly did we spend $47,000 on?” Herby was ready. He’d prepared for this.
“Transportation costs, moving product from suppliers to distribution points, truck rentals, gasoline, tolls, driver payments, security escorts—it all adds up. May was a high-volume month.” Bumpy analyzed it. “Transportation cost us $47,000 in one month. That seems high. Last year we were spending $20,000 a month on transportation.”
“Why is it more than double now?” “Fuel prices went up. Security got more expensive. We’re moving more product than last year. The numbers make sense if you look at the volume.” Bumpy didn’t argue, but he didn’t believe it either. Not entirely. His instinct told him Herby was lying, or at least not telling the whole truth. But he couldn’t prove it. Not yet.
So he did what smart criminals do when they suspect betrayal. He watched, he waited, he gathered evidence. Bumpy hired an outside auditor, a Black accountant from Chicago named Calvin Reed, who had no connection to Herby and no loyalty to him. “Calvin, I need you to review my financial records for the last six months. Quietly, without Herby knowing, I think money is disappearing. I need proof.”
Calvin spent three weeks reviewing documents that Bumpy secretly provided him: copies of ledgers, bank statements, expense reports. By the end of July, Calvin had reached his conclusion. “Mr. Johnson, your accountant is stealing from you. Conservatively, I estimate he’s taken approximately $1.8 million over the last six months, maybe more.”
The scheme is sophisticated. It’s inflating expenses, creating phantom costs, and redirecting funds to accounts it controls. This is systematic embezzlement.” Bumpy wasn’t surprised. Angry, but not surprised. “Can you prove it? Evidence that will hold up in court?” Calvin shook his head. “Prove it? Yes, I can document everything. But cut, Mr. Johnson,
You can’t go to court. Your entire financial operation would be exposed. Federal authorities would investigate. You would face charges of tax evasion, money laundering, racketeering. Going to court means going to prison. You can’t use the legal system to resolve this.” Bumpy knew Calvin was right.
This had to be handled privately, permanently. “Do you know where the money is?” “He’s moved it to accounts in various places. Some in the Bahamas, some in Switzerland, some in Cuba. He’s preparing to flee. My guess is he’s going to disappear soon. As soon as he feels he has enough, he’s going to vanish. Probably to Cuba. That’s where most of the money is.” Bumpy made a decision.
I wouldn’t confront Herby. I wouldn’t warn him. I’d let Herby think he was getting away with it. Let him escape. And then I’d show him what happens to those who steal from Bumpy Johnson. “Calvin, I want you to monitor Herby’s movements. Watch his accounts. If he starts moving more money to Cuba or if he books a trip, you tell me immediately.”
“I want to know the instant he flees.” Calvin agreed. For the next month, he watched. By mid-August, Herby’s activity intensified: large cash withdrawals, transfers to Cuban banks, plane tickets purchased. Calvin reported to Bumpy. “He’s going to flee soon. My guess is this weekend. He’s liquidating everything.”
Converting to cash, booking flights. That’s it.” Bumpy got ready. He called his most trusted lieutenant, Marcus Webb. “Marcus. Herby’s going to Cuba. Probably Saturday. I want him dead within hours of arriving. Not days, not weeks: hours. I want to send a message. You rob me. You don’t get to enjoy it. You die before you can even unpack.”
“Can you fix this?” Marcus thought. “Cuba is complicated. Another country, different laws, but we have contacts there. Sam Giancana has people running casinos in Havana. Meyer Lansky owns hotels. Santo Trafficante handles operations. They owe us favors. I can collect on those favors. I’ll have people waiting when Herby arrives, but it’s going to be tight. If his flight lands at 6:00 p.m.
And we need him dead in two hours, that’s 8:00 p.m. That’s fast. Very fast. I don’t care if it’s fast. I care that it’s done. Herby has two hours. That’s all. Two hours to realize he made a mistake. Two hours to understand he’s not safe. Then he dies and his body is returned to New York in a coffin with a note.
I want everyone who works for me to understand that stealing leads to death: swift, permanent, inevitable.” Friday, August 22, 1958, 1:18 pm Calvin Reed calls Bumpy. “Herby booked a Pan Am flight for tomorrow, Saturday. Leaves 3:47 pm Arrives in Havana 6:12 pm Today he withdrew 2 million in cash. Two suitcases. He’s on the run.” Bumpy calls Marcus. “Tomorrow.
3:47 pm departure. 6:12 pm arrival in Havana. I want him dead by 8:12 pm. Exactly 2 hours.” Marcus makes calls. International calls. Havana. Santo Trafficante Jr., head of the Tampa mafia who controls operations in Cuba. “Santo. This is Marcus Webb. Bumpy Johnson’s lieutenant. We need a favor. We have a guy arriving in Havana tomorrow.”
6:12 pm Pan Am flight from New York. His name is Herbert Goldstein. White, 42, accountant. He stole $2 million from Bumpy and is on the run. We need him dead within two hours of landing. Can you take care of it?” Santo doesn’t hesitate. “Bumpy did me a favor in ’54. I remember. Consider it done. Give me the details. Flight number, description.
I’ll have people at the airport. Your guy doesn’t make it to a hotel. We’ll grab him on the baggage carousel. Dead in two hours. Guaranteed.” Marcus gives him everything: flight number, physical description. “Two suitcases, one with clothes, one with cash. The cash is coming back to New York. It’s Bumpy’s money. But more important than the money, the body is coming back in a coffin with a note.”
Bumpy wants to display the body. Let everyone see what happens when you rob.” “Understood. Body and cash returned. Anything else?” “Speed. Bumpy wants this done in exactly 2 hours. Plane lands 6:12 pm. Target dead by 8:12 pm. No later. Time matters. The message is: you rob, you don’t have time to enjoy it.”
“You die instantly. 2 hours.” “I’ve got it. Consider it done.”
Saturday, August 23, 1958. 3:47 pm. Idle Wild Airport, New York. Herbert Goldstein boards Pan Am Flight 441 to Havana. He is nervous but excited. Two suitcases: one with clothes, one with 2 million in cash. 50 and 100 dollar bills. Packed carefully. Approximately 40 pounds of money.
Herby is dressed in his best suit, sunglasses, and hat, trying to look casual, trying to look like a tourist going to Havana for gambling and entertainment, not a thief fleeing with stolen millions. The plane takes off at 3:47 pm. Three-hour flight. Herby settles into his seat, orders a whiskey, tries to relax: he did it, he pulled it off, he stole two million and escaped.
By the time Bumpy realized the money was gone, Herby would be safely back in Havana, living in a nice apartment, maybe buying a small business, enjoying his retirement at 42 with more money than he could ever earn in 20 lifetimes of legitimate accounting. He won. He beat the system. He outsmarted Bumpy Johnson. At least, that’s what he thinks. 6:12 pm
José Martí International Airport, Havana, Cuba. Pan Am Flight 441 lands. Passengers disembark. Herby walks through the terminal and heads to baggage claim. Nervous but confident. He’s in Cuba. Outside of U.S. jurisdiction, safe. He retrieves his two suitcases. Both are there. Both intact. The cash is still there. He can tell by the weight.
Everything is going according to plan.
Two men approach. Cuban, well-dressed, professional. One speaks English.
—Mr. Goldstein.
Herby freezes. How do they know his name?
—Who are you?
—Friends of Mr. Trafficante. He would like to speak with you. Please come with us.
Herby’s mind races. Santo Trafficante. The Tampa mafia boss who controls operations in Cuba. Why does he want to talk? Did Bumpy call earlier? Is this a problem? Herby tries to stay calm.
—I don’t know who she is. I’m just here on vacation.
The second man pulls out a concealed weapon and presses it against Herby’s ribs.
—This is not a request. Come with us now or we’ll kill you here and take the suitcases anyway.
Herby has no choice. He follows them. They lead him outside. A black Cadillac is waiting. They force him inside. They drive off. Herby is terrified. This is wrong. This isn’t how things were supposed to go. He was supposed to arrive, take a taxi, check into a hotel, and start his new life, not be abducted by mobsters at the airport.
The car drives for 12 minutes and arrives at the Hotel Nacional, Havana’s most famous hotel, controlled by the mafia.
Herby is taken to a room, fifth floor, suite, expensive, empty except for one man. Santo Trafficante Jr. is sitting in a chair smoking a cigar.
—Mr. Goldstein, welcome to Havana. I understand you stole 2 million from Bumpy Johnson. Is that correct?
Herby’s voice trembles.
—I don’t know what you’re talking about. I’m just a tourist.
Santo signals to one of his men. The man punches Herby hard in the stomach. Herby collapses, gasping for breath.
—Let’s try again. He stole 2 million from Bumpy Johnson. He flew here thinking he’d be safe. He was wrong. Bumpy Johnson is my friend. He called me and asked me to take care of this. So here we are.
Herby can barely breathe.
—Please, I can pay you. I have the money. 2 million. We can split it.
“The money comes back with Bumpy. It’s his money. You stole it. We’re giving it back. But you… you don’t come back. Well, you do come back, but not alive. Bumpy wants you dead. And he wants your body sent back to New York in a coffin with a note. So everyone knows what happens to thieves.”
—Please. No. I’ll give you your money back. I apologize. Please don’t kill me.
Santo looks at his watch.
—It’s 6:47 pm. His plane landed at 6:12. 35 minutes ago. Bumpy wants him dead by 8:12. That gives us 1 hour and 25 minutes. Plenty of time.
He nods to his men.
—Do it. Quickly. I don’t want a disaster in this hotel.
One of the men pulls out a silenced pistol. He walks behind Herby. Herby cries, he begs.
—Please, no. Please. I have a wife. I have children. Please.
The man shoots him in the back of the head. Execution style. Herby falls. He dies instantly.
Santo looks at his watch again.
—6:48 pm Just in time.
7:15 pm Santo’s men work efficiently. They have a coffin ready, pre-arranged and ordered earlier that day. They place Herby’s body inside, seal it, and affix a note to the outside, written by Santo according to Bumpy’s instructions.
Herbert Goldstein stole $2 million at 3:47 pm. Dead at 6:48 pm. Flight time: 3 hours. Survival time in Cuba: 36 minutes. Total: 3 hours 36 minutes from robbery to death. Nobody steals from Bumpy Johnson. BJ.
The two suitcases, one with clothes, the other with 2 million in cash, are loaded in a separate shipment.
Everything goes to the airport. A direct cargo flight to New York. It arrives Sunday morning; the coffin and the money will be delivered to an address in Harlem. Bumpy’s warehouse: private, discreet.
Sunday, August 24, 1958, 9 a.m. Bumpy’s Warehouse, Harlem. The coffin arrives along with two suitcases. Marcus Webb is waiting. He opens the coffin. He confirms that Herbert Goldstein is dead. One shot to the head: clean, professional. Exactly as requested.
Marcus opens the suitcases. One contains clothes, the other cash. He counts it. 2 million. All of it. Recovered.
Marcus calls Bumpy.
—It’s done. Herby is dead. The body and the money are here. Santo handled it perfectly. Timeline: The plane landed at 6:12 pm on Saturday. He was dead at 6:48 pm 36 minutes. Even faster than the 2 hours he asked for.
Bumpy satisfied.
—Good. Display the coffin. I want everyone who works for me to see it. I want them to read the note. I want them to understand: stealing from me means death. Immediate. You don’t enjoy the money. You don’t escape. You die within hours.
That’s the message.
Monday, August 25, 1958. The news spreads through Bumpy’s organization. Herby Goldstein, the trusted accountant, stole $2 million and fled to Cuba. He was dead 36 minutes after landing. His body was sent back in a coffin. The money was recovered. The note is explicit.
Nobody steals from Bumpy Johnson.
The impact is immediate. Everyone who works for Bumpy—accountants, lawyers, distributors, enforcers, everyone—understands. Stealing is suicide. You might get away with it for a few hours, you might even make it to another country, but you won’t survive. Bumpy’s reach is international. His response is swift. His justice is final.
The investigation. Cuban authorities are investigating the death of an American tourist, Herbert Goldstein, found shot to death in the Hotel Nacional, but the investigation is going nowhere. Hotel staff saw nothing. Security cameras malfunctioned. There are no witnesses. Santo Trafficante’s organization has too much control over Havana’s infrastructure.
The case is closed, unsolved. Just another American dead in a city rife with violence.
US authorities are investigating Herby’s disappearance. His wife reports him missing. His flight to Havana is traced, but that’s where the trail ends. There’s no evidence he arrived. No hotel reservations, no witnesses, no body. The case goes cold.
Herby Goldstein vanished somewhere between New York and Havana. Presumed dead. Unsolved. Only Bumpy’s organization knows the truth. Herby stole $2 million, fled to Cuba, was dead within 36 minutes. The body returned. The money was recovered. Perfect revenge.
The message.
The story becomes legendary within Bumpy’s organization. “Herby the accountant. He thought he was clever. He thought he could steal 2 million and escape to Cuba. He thought he’d be safe in another country. He was wrong. He had 36 minutes of freedom in Havana. 36 minutes to realize his mistake. 36 minutes to understand he wasn’t safe. Then he died. And his body came back in a coffin with a note explaining exactly what happened.”
No one ever stole from Bumpy Johnson again. Not accountants, not lawyers, not distributors, no one. Because everyone knew: steal from Bumpy, and you die fast, permanently, inevitably. Even if you flee to another country, even if you think you’re safe, Bumpy’s reach is global. His response is measured in hours, not days. You steal at 3:47 pm
And you’re dead by 8:12 pm. That’s not a threat. It’s a documented fact. A body in a coffin. A note explaining why. A lesson everyone learned.
August 23, 1958. 3:47 pm Herby steals $2 million and flees to Cuba. August 23, 1958. 6:48 pm Herby is dead in Havana. 3 hours. That’s how long Herbert Goldstein enjoyed his stolen millions.
Three hours from robbery to death. He spent more time on the plane than he was alive in Cuba. That’s not revenge. That’s not even retaliation. That’s Bumpy Johnson proving that robbing him means instant death. You can escape geographically. You can flee to another country, but you can’t escape the consequences.
They follow you, they find you, they kill you within hours. Proven, permanent, absolute.
