The Hitman Who Made Millions (And Never Carried a Gun)

Added: 2026-05-30

[00:00:00]The 12th of June 1941, 11:00 p.m., Sing Sing Prison, New York.

[00:00:06]Harry Strauss was walking the last 40 ft of his life. He was escorted by guards down a pale green hallway toward the death chamber. The room smelled of ozone and industrial bleach. He did not fight.

[00:00:19]He did not scream. He sat in the solid oak electric chair known as Old Sparky.

[00:00:25]The guards strapped thick leather bands across his chest and legs. They placed a sponge soaked in his shaven head. When the switch was thrown at 11:04 p.m., 2,000 V of electricity surged through his body. He was pronounced dead 3 minutes later. This was not just another mobster getting justice. Harry Strauss, known on the streets as Pittsburgh Phil, was the most prolific and innovative contract killer in the history of the American Mafia. He did not just commit murders. He industrialized them. He was a man who allegedly committed over 120 homicides across the United States, yet he never carried a weapon. He viewed murder not as a crime of passion, but as a logistical puzzle. He dressed like a Wall Street banker and killed with the cold precision of an assembly line machine. This is the story of how one man turned the underworld into a corporate enterprise. From secret boardroom meetings in Brooklyn candy stores to cross-country train rides, from the perfection of the untraceable hit to the ultimate betrayal that brought down an empire. This is the rise, the reign, and the violent fall of Harry Strauss and the enforcement squad the press famously named Murder Incorporated. But here is what the history books do not tell you.

[00:01:52]Harry Strauss did not just follow orders. He invented a methodology so perfect that the FBI spent a decade trying to understand it. And if his own best friend had not turned against him, he might have died an old, wealthy man in a mansion instead of in the electric chair. To understand how a man becomes a machine, we need to go back to the beginning.

[00:02:16]Brownsville, Brooklyn in the 1920s was a pressure cooker of poverty and ambition.

[00:02:23]It was a neighborhood of crowded tenements, pushcart vendors, and desperate people trying to survive.

[00:02:30]Harry Strauss was born into this world in 1909.

[00:02:34]He was a smart kid, but the schools in Brownsville did not offer a way out. The streets did. By the time he was 19, Harry was running with local gangs.

[00:02:44]Harry Strauss, 22, tall, handsome, with perfectly slicked dark hair, was known for one distinct trait. He never raised his voice.

[00:02:55]While other street thugs yelled and postured, Harry whispered. He was impeccably dressed. He eventually owned over 50 custom-tailored suits. He looked like a young Hollywood executive.

[00:03:08]He tipped well at restaurants. He adored his wife. He drove his family to the park on Sundays. And from Monday to Saturday, he murdered people for a living.

[00:03:18]You have to understand the landscape of organized crime. In 1931, the Castellammarese war had just ended.

[00:03:26]Lucky Luciano and Meyer Lansky had successfully reorganized the Italian and Jewish mobs into a single national crime syndicate. They created a commission.

[00:03:38]A board of directors for the underworld.

[00:03:41]But a board of directors is useless if it cannot enforce its rules. Luciano and Lansky realized they had a massive problem. When a local mobster killed a local rival, the police knew exactly where to look. The motive was obvious.

[00:03:56]The weapon could be traced. Local hits were bad for business. They needed a solution. They found it in Brooklyn. A brutal mob boss named Albert Anastasia, 29, built like a heavyweight boxer with a terrifying temper, was put in charge of a new unit. Alongside a Jewish labor racketeer named Louis Lepke Buchalter, they formed an elite squad of killers based out of a 24-hour candy store in Brownsville called Midnight Rose. This was not a gang.

[00:04:28]It was a corporate department. Their only product was death. The press would later call them Murder, Incorporated, and Harry Strauss quickly became their star employee.

[00:04:40]Harry was different from the other killers. He did not like guns. Guns left ballistics. Guns made noise. Guns were heavy and could be found by the police during a routine stop. Harry believed that bringing a weapon to a hit was a sign of amateurism. This philosophy changed everything.

[00:05:00]Let us break down exactly how the Murder, Incorporated system worked.

[00:05:05]This is the five-step scheme that made them untouchable for a decade.

[00:05:11]First was the opportunity. The syndicate had a problem in another state. Maybe a bootlegger in Detroit was not paying his taxes. Maybe a union boss in Florida was asking too many questions.

[00:05:24]Second was the inside connection. The commission in New York would hold a formal vote. If the target was approved for death, the local boss in Detroit or Florida was strictly forbidden from doing the job himself.

[00:05:39]Instead, he would send a request and a payment to Brooklyn. Third was the execution logistics. This is where Harry Strauss shined. Harry would receive the contract from Albert Anastasia. He would pack a beautiful leather suitcase.

[00:05:55]Inside, he packed silk shirts, tailored slacks, and shaving gear. No guns. No knives.

[00:06:04]He would board a luxury train from Grand Central Station, tipping the porter heavily, and travel across the country looking like a successful businessman.

[00:06:14]Fourth was the local purchase. Upon arriving in the target city, Harry would meet a local contact called a point man.

[00:06:22]The point man provided the exact location of the target. Harry would then walk into a random local hardware store.

[00:06:30]He would buy an ice pick, or a heavy rope, or a fire axe. He paid in cash.

[00:06:36]Fifth was the problem avoidance. Harry would find the target, execute the hit using the local tool, and simply leave the weapon at the scene.

[00:06:47]He would walk away, board a train back to New York, and be eating dinner in Brooklyn by the time the local police found the body.

[00:06:55]The local police had a dead body and a murder weapon bought in their own town.

[00:07:01]They had a list of local suspects with motives, but none of the local suspects had committed the crime, and the man who did commit the crime had no motive, no connection to the victim, and was already 1,000 miles away.

[00:07:16]It was a ghost protocol, and it worked flawlessly. Harry Strauss was paid a flat salary of $250 a week, plus bonuses ranging from $1,000 to $5,000 for out-of-town jobs.

[00:07:31]In the 1930s, this made him a millionaire by modern standards, but that is not the crazy part. The crazy part is how creative Harry became with his methods. By 1935, Harry was traveling constantly. He operated in Chicago, Detroit, Los Angeles, and Miami. He was a phantom, but his most infamous work happened closer to home.

[00:07:56]Consider the case of Walter Sage. Walter Sage, 35, a nervous man with a gambling habit, was running slot machines for the mob in the Catskill Mountains.

[00:08:07]In the summer of 1937, the syndicate discovered that Sage was skimming profits. He was stealing roughly $3,000 a week from the bosses.

[00:08:19]The commission ordered a hit.

[00:08:22]The bosses did not want Sage shot. They wanted him to disappear to send a quiet message. Harry Strauss was given the contract. He drove up to the Catskills with a partner. They did not bring weapons.

[00:08:35]Instead, they took Sage out for a friendly drive in the mountains. Harry sat in the backseat. As the car rolled down a quiet dirt road, Harry produced a simple ice pick he had acquired locally.

[00:08:49]He stabbed Sage 32 times in a matter of seconds. Time of death was roughly 11:30 p.m., but the execution was only half the job. The disposal was the real art.

[00:09:01]Harry and his partner drove the body to a secluded area near Swan Lake. They found an old, heavy slot machine frame.

[00:09:10]They tied Sage to the slot machine using thick rope. It was poetic justice. The man who stole from the slot machines was anchored to one forever. They dumped him into the deep water of the lake. The plan was perfect, except for one detail.

[00:09:26]The rope they used was slightly degraded. Two weeks later, a group of tourists were boating on Swan Lake. The rope snapped underwater. The bloated body of Walter Sage floated to the surface.

[00:09:39]Investigators recovered the body and noted the 32 puncture wounds, but they had no witnesses.

[00:09:46]They had no weapon.

[00:09:48]Harry Strauss was questioned, but he had a perfect alibi back in Brooklyn. The case went cold immediately. This was the peak of Murder Incorporated. They were untouchable. They operated out of Midnight Rose Candy Store, sipping egg creams and taking phone calls from across the country ordering hits like they were ordering takeout food. Harry Strauss was respected, feared, and rich.

[00:10:15]But here is where it gets interesting.

[00:10:17]Any system built on absolute ruthlessness eventually consumes itself, and the seeds of Harry's destruction were not planted by the police. They were planted by the very men he worked with.

[00:10:31]By 1939, the political climate in New York was shifting rapidly. A crusading district attorney named Thomas Dewey was making national headlines by targeting organized crime. Dewey was smart.

[00:10:46]He realized that investigating local murders was pointless. He needed to target the corporate structure of the syndicate. He appointed a relentless prosecutor named Burton Turkus to dig into the Brooklyn underworld.

[00:11:00]The pressure was mounting. Detectives were sitting outside Midnight Rose Candy Store taking photographs. Informants were being squeezed. The syndicate bosses started getting paranoid. When mobsters get paranoid, they make mistakes.

[00:11:16]Harry Strauss was a professional, but he was surrounded by men who were starting to panic. One of those men was his frequent partner, Martin Goldstein.

[00:11:27]Goldstein, 34, nicknamed Bugsy, was loud, erratic, and lacked Harry's cold discipline.

[00:11:34]On the 4th of September, 1939, Harry and Bugsy were handed a contract to eliminate a low-level thug named Puggy Feinstein. Feinstein had crossed Albert Anastasia. It was supposed to be a routine job. Harry and Bugsy lured Feinstein into a residential house in Brooklyn. Harry, true to his method, did not use a gun. He used a simple clothesline rope to strangle Feinstein in the living room. But this time, the disposal was sloppy. They did not have a lake. They did not have an incinerator.

[00:12:11]They dumped Feinstein in a vacant lot in Brooklyn and set the body on fire to destroy the evidence.

[00:12:18]The fire attracted attention. The police arrived before the body was fully destroyed. Forensic investigators recovered a partially burned piece of rope. Time of death was estimated at 2:15 a.m. Normally, this would not matter. The ghost protocol should have protected Harry. But there was a fatal flaw in the Puggy Feinstein hit. There was a witness. Remember this name, Abe Reles.

[00:12:47]Abe Reles, 33, short, built like a bulldog, was another top killer for Murder Incorporated. He was vicious.

[00:12:56]He once murdered a parking lot attendant just for being slow to bring his car.

[00:13:01]Reles was in the house when Harry and Bugsy strangled Puggy Feinstein. In early 1940, the police arrested Abe Reles on a separate murder charge. Reles was sitting in an interrogation room. He looked at the evidence against him. He realized he was going to the electric chair.

[00:13:20]Reles did the math. The syndicate demanded absolute loyalty, but Reles loved his own life more than the syndicate. On the 23rd of March, 1940, Abe Reles made a decision that changed the history of the American Mafia. He asked for a glass of water, looked at prosecutor Burton Turkus, and said he wanted to make a deal.

[00:13:42]Abe Reles began to sing, and he did not just give up small names. He gave up the entire corporate structure of Murder, Incorporated. He explained the five-step system. He explained the out-of-town hits. He explained the icepicks and the ropes. He gave the police dates, times, and exact dollar amounts. He confessed to his own crimes and implicated everyone around him. The canary had sung. The dominoes began to fall.

[00:14:13]Within weeks, police rounded up the top killers in Brooklyn. Harry Strauss was arrested while walking out of a high-end tailor shop. He was wearing a brand new $200 suit. He did not resist. He assumed he would beat the charge. He had beaten them before. But when Harry sat in the Brooklyn courthouse, he saw Abe Reles walk through the double doors and sit in the witness box. Harry's cold, dead eyes locked onto Reles.

[00:14:41]For the first time in his life, Pittsburgh Phil realized he was trapped.

[00:14:46]The system he helped build was now being used against him. Reles testified about the Puggy Feinstein murder. He provided details that only a man in the room could know. He described how Harry wrapped the clothesline rope around Feinstein. He described the exact words spoken.

[00:15:06]Harry Strauss was a master tactician.

[00:15:08]When his physical escape routes were cut off, he decided to create a psychological one. He launched one of the most bizarre legal defenses in courtroom history. Harry decided to fake insanity.

[00:15:21]For a man who prided himself on impeccable grooming and custom suits, this was a massive sacrifice. Harry stopped bathing. He let his hair grow wild. He stopped shaving, developing a thick, unkempt beard. When he was brought into the courtroom for the trial in September 1940, the press could not believe their eyes.

[00:15:44]The dapper hitman looked like a wild animal. His behavior in court was deeply disturbing. Harry would refuse to speak to his lawyers. He would stare blankly at the ceiling for hours.

[00:15:56]At one point during the testimony, Harry leaned down and began violently chewing on the leather strap of his briefcase.

[00:16:03]He mumbled incoherently. He wiped his nose on his sleeve. You have to appreciate the strategy here. If Harry was deemed legally insane, he could not be sent to the electric chair. He would be sent to an asylum.

[00:16:18]From an asylum, he could eventually escape or bribe his way to freedom. It was his ultimate ghost protocol.

[00:16:26]The courtroom was captivated. Defense psychiatrists testified that Harry was suffering from severe psychosis.

[00:16:34]They argued the stress of his life had finally broken his mind.

[00:16:38]But prosecutor Burton Turkus was not buying it. Turkus brought in his own medical experts. More importantly, he brought in prison guards who testified that when Harry was alone in his cell, he acted completely normal. He played cards. He read the newspaper. The insanity only appeared when the courtroom doors opened. The trial lasted 2 weeks. The jury deliberated for only a few hours.

[00:17:05]On the 19th of September, 1940, the jury returned to the courtroom. The foreman stood up. Harry Strauss sat at the defense table, mumbling and chewing on his fingernails.

[00:17:18]The verdict was guilty of murder in the first degree. The sentence was death by electrocution. When the judge read the sentence, Harry Strauss stopped mumbling. The facade cracked for just a second. He looked at the judge with total clarity, his eyes burning with hatred. The performance was over. Harry and his partner Bugsy Goldstein were transferred to death row at Sing Sing prison. They were placed in tiny concrete cells in the block known as the dance hall. For months, Harry's lawyers filed appeals. They tried to take the case to the Supreme Court, but the evidence provided by Abe Reles was too strong. Speaking of Abe Reles, what happened to the man who broke the Mafia code? The police knew Reles was the most important witness in American history.

[00:18:11]They locked him in room 417 of the Half Moon Hotel in Coney Island. The room was guarded 24 hours a day by six police officers. Reles was supposed to testify against the biggest boss of all, Albert Anastasia. But on the morning of the 12th of November, 1941, the body of Abe Reles was found dead on the roof of a kitchen extension directly below his hotel window. The official police report claimed he tried to escape using tied bed sheets and fell. But the street knew the truth. Reles was thrown out of that window by the very cops paid to protect him. The mob had gotten to the guards. The canary could sing, but he could not fly. The death of Abe Reles saved Albert Anastasia from the electric chair, but it was too late for Harry Strauss. His appeals had already run out. Which brings us back to that pale green hallway on the 12th of June, 1941.

[00:19:12]In his final days, Harry dropped the insanity act completely. He showered. He shaved his thick beard. He requested a tailored suit for his final walk, though the prison denied it, forcing him to wear the standard gray uniform. He ate a final meal of roasted chicken, french fries, and a large slice of strawberry shortcake. When the guards came for him at 10:55 p.m., he was calm. Bugsy Goldstein was executed first. Harry sat in his cell and listened to the hum of the generator. He did not flinch. When it was his turn, Harry walked into the death chamber. He looked at the witnesses sitting behind the glass. He did not offer a final statement. He sat in the chair, the ultimate professional to the very end, accepting the cost of doing business. The execution of Harry Strauss marked the end of an era. The National Crime Syndicate learned a brutal lesson. Murder Incorporated was too big, too structured, and too vulnerable to informants. The bosses realized that having a dedicated squad of killers was a liability.

[00:20:23]After 1941, the Mafia changed its strategy. They decentralized.

[00:20:29]Hits were handed out strictly on a need-to-know basis. The corporate assembly line of murder was dismantled.

[00:20:37]Harry Strauss spent a decade building power in the shadows. He earned millions. He revolutionized organized crime. He turned homicide into a logistical masterpiece.

[00:20:49]But, in the end, he traded it all for a wooden chair and 2,000 volts of electricity.

[00:20:56]That is the real story of the Mafia. Not the tailored suits, not the untouchable myth, just the inevitable grinding price of betrayal. Harry Strauss thought he had removed the human element from murder.

[00:21:10]He forgot that the human element is exactly what brings empires down.