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Rum Runners of Eight Mile Road

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You have probably never heard of the Rum Runners in California’s Central Valley, whose operation ran during the 1930’s. It is quite a puzzling urban legend that surrounded the San Joaquin area for generations. However one story of murder, love, and insanity is foreshadowed in the Gregory brothers legend which is still confusing and conflicting to this day.

Our story kicks off in the year 1931 in the midst of the Great Depression. Of the areas in the United States that were often hit hard by bad times. The Central Valley was one of the typical regions hit by depression: High unemployment, lots of crime on the street, and little work. Often the only two jobs that you could find in the area were in agriculture, or in rum running. The Gregory boys were no exception, often making and running rum and other illegal temptations within the deep depths of the farms and walnut groves which littered over the Eight Mile Road, a long country road east of a small city.

Although many were captured by the police for rum running due to the lack of speed in their cars, the Gregory boys were an exception due to James, who was a skilled driver, and his trusty Plymouth 30U Coupe which could outrun any of the outdated and underpowered police cars of the day. On top of their fast car, they were also skilled manipulators, often driving on Eight Mile Road due to the twists and turns which made capturing the boys through the fields and groves of walnut trees nearly impossible. James pulled off a daring escape by turning a hard right to avoid turning into the Calaveras River which was at the end of Eight Mile and merged into another street. It was pretty practical, leading cops to curve, then take a hard right. They only used this method when carrying large quantities of booze, knowing the smaller loads were easier to slick past the other roads.

However, the other brother William, was crazy and unlike his calmer brother, he was always suspicious of everyone he came in contact with, often very schizophrenic and hostile towards even his own brother . On top of being local alcohol smugglers, they were often notorious hitmen. At one point, killing some of the local cronies which he used as a decoy because one time, he wasn't driving quick enough.

They dumped the bodies of their enemies and witnesses in the Calaveras River and used cement blocks to sink the bodies. This became an aspect of everyday life to the men and forced many of the people in the area to look the other way when it came to crime investigations and police involvement.

James and William, often known as their nicknames, “Starch and Poison.” Oftentimes, due to brutality of their murders, they were known to give their presumed victims an option: Getting the body dumped alive tied to a cement block, or eating their “last meal” which was a piece of bread coated with enough poison to kill an elephant. The occupant would often choose the “last meal” option and had their dead body thrown in the river anyways, but occasionally out of compulsion William would shoot one in the head. with no option.

Although not known until later, upon the discovery of William Gregory’s journal, William had a third known accomplice who was a local prostitute, Betty Dupree. She often seduced the local cops and got the two guys out of trouble by faking cops out, while the others would often be chased by running out in the middle of the road, trying to stop the cops. She would make up some story giving them time to get away. This came from a local excerpt from William's journal.

September 3, 1931Edit

Betty is one of the smartest women in the world. She figured out a new way of tricking the fuzz into believing that we went up on Highway 88, giving us time to escape. She is just as beautiful as she is smart. For some reason I have been having these dreams about me and her on the river but all I see is the body of some dead woman. I don't know what is going on, probably just from lack of sleep.

William began to have constant nightmares about the people he killed, and for some reason had the recurring nightmare of killing some woman and burying her near the riverbed. This left him very jumpy when James would come to talk to him. James, blowing it off as a result of little sleep, just said it comes with the job of killing people. William, however could not get that out of his head. The biggest experience he had was when they were in their local hideout. William was shaving, when suddenly he dropped the razor. When he picked it up, he was looking at an image he would never forget. In the mirror was himself, but soaked in water and covered with cuts and bruises like he was one of the victims in the river. He screamed and ran back, falling over, as he did. When he looked back in the mirror, it was just him. He wrote this in his journal explaining the situation.

September 6, 1931Edit

I was shaving when I dropped my razor on the floor, what I saw in the mirror was the shadow of a man that was dead or near dead. On closer inspection, it was me in that mirror, cuts and bruises with a gunshot in the head. Just like I give when killing another person. I saw myself also soaked as if I had dropped in the local river. Then falling over what seemed to be a puddle of water, I fell out of that trance. Then everything was normal again, I know that I am suffering from lack of sleep, but is it really causing me to hallucinate? To see the dead as if I was one of their own? No… No, it cant be.

Over the next few weeks, William began to fall into a massive depression, leaving James to do all of the dirty work by throwing the bodies in the river. On the other hand, William began to hear stuff at the hideout. It sounded like running water and shuffling around like someone was dragging something heavy. He looked out the window. Nothing. He then continued to go to sleep and heard the same dragging sound and drips of water. Then a knocking on the door, upon inspection, he opened the door finding nothing outside. He then shouted obscenities, like, “coward” and “monsters”. Then Betty woke up and told him to go to sleep, and she began comforting him. He said he was hearing things but she said there was nothing out there for miles, and she heard nothing. He then just sat there with those big black eyes like he didn't sleep for days, or weeks even. Then shouting at her he said, “Go to hell,” and stormed into the room, being once again taunted by the sounds of water and dragging noises.

Over and over again, night after night, he began hearing those dragging sounds, driving him more and more mad and becoming schizophrenic. He began punching trees out of anger, trying to find an answer in there, being scared and confused. He didn't know what to do after his knuckles were bleeding and hurt. He began to become hostile and yelled at them. Then Betty decided it was best if they took a nice picnic over by the riverfront.

Then later on a nice fall day, Betty and William were on the riverfront having a nice picnic with a good bottle of fancy cider and some fresh sandwiches, when an argument began about what they should do with the money. She said they should move down to South America, where they could live the rest of their lives away from the crimes they committed. However, he believed that they would never be caught and began joking around, when all of a sudden, he saw a man rise out of the river. The man began walking slowly towards them. He pointed franticly at the river, and when she looked nothing was there. Then the man appeared again, he began taking the shape of a rotten shell of a man covered in water, and a bullet shot to the head. William began to sound hostile and pulled the bottle of cider up in his hand, ready to fight when the specter was standing there. He asked, “What do you want?” in a gasping voice. He then ran to a tree and busted the cider making the glass into a sharp weapon. Then running into the river, he began shouting as the specter just slowly went into the river, maniacally laughing just like some joke saying, “Her,” in a loud voice.

Then, just as Betty said she was going to leave, William snapped and grabbed the bottle of cider, and smashed it over Betty’s head with a glancing blow. This didn't stop as Betty was still running in extreme paranoia. She began running through to the old riparian vegetation of oak trees and bushes, running across the road into a walnut farm with William coming up the rear. She hid in a small milk shack hiding for only a few minutes with William slowly following behind. He began shouting, “They want you Betty,” then paused and said, “They want you to join the party with them in the river.” Then he collapsed with the bottle at the side of his hand, cutting himself with the blade as if he enjoyed it. She saw that as an opportunity to escape and began to bolt out of the door of the shed. That was when William pulled the gun out of his side holster, pulled the trigger, and shot her in the head and back six times.

Laying on the ground and still breathing, she then said, “Why William?” He then looked at her with that maniacal grin and said, “Because they want you down there next to them.” Then in a fit of rage, he started hitting her over and over again until the body was unrecognizable. Out of a fit, he grabbed the body and ran over by the river dragging Betty with him. He dug a large hole and threw the remains in it, close to where he dumped the bodies with cement. He spent hours covering up the remains trying to hide the mangled up mess.

After committing the terrible deed he began to leave when he heard a faint scream yelling, "Who's there?" getting no response. Brushing it off, he left the gravesite for the river.

He then cleaned himself in the river when he began to feel stressed out and confused on why he killed her so fast. This is where he writes in his next journal entry.

November 1, 1931Edit

I had to kill her, she was on to me. The men at the river wanted me to kill her so... I drew my gun and pulled the trigger. I shot her six times in the back with my revolver, and then dragged the body and buried her next to a tall oak tree. She will be with them and myself in the time will come. I now know that the dream I had was only a reality of what was to come. The time will come when she will be with me. The men in the river said it would happen. It will happen. It will happen. It will happen. It will happen.

After killing her he went back to James’s place, up the Calaveras River several miles, to tell him what happened and the gruesome fate of Betty, to which James said, “Women come and go.” That was when he began to tell him about the story of his nightmare of the dead body. James was skeptical so he just brushed it off as bullshit. James said that he was probably under a lot of stress and that she was going to rat on them anyways. William, on the other hand, decided to take a nap and fell asleep.

That was when he was awaken by a large thump in the middle of the night. He began to hear voices that resembled Betty's. He thought it was all over. Just another day and the stress would be over. He brushed it off and fell asleep again. Then he heard it again, but a faint scream, then the words, “William and Betty will be together forever,” and it echoed. He then took half a bottle of whiskey and fell asleep.

He then began to have odd dreams about an empty grave by the river, then betty appeared, covered in blood and dirt saying, “We will be together, forever,” over and over again. Then he had flashes came to him of the river and the road, at which he was going a daunting speed. Then at the turn, he saw a splash and woke up. These dreams persisted over the next few days and didn't seem to get better. It always ended with some sort of person or object crashing into the river. He wondered what it meant, but had no answer.

The worst dream was that of a battle of some kind as if he was fighting in Spanish Colonial times. He saw men, women, and children being slaughtered by the river bend leaving hundreds of littered skulls around the river. Then waking up in panic to the sounds of laughing. Then several days later, William began his body burying and killing routine again, trying to get his mind off of the dreams. He went to the dump sight when he began to hear a faint, unrecognizable whisper. He brushed it off, thinking it was the wind. Then the voices began saying, “Will,” and, “I know what you did.” William began to feel hazy. Then he saw the worst of his visions, his hands began raising out of the water grabbed what looked like mangled remains of bone and vegetation decomposing in the freshwater river. Then he saw hundreds of decomposed hands trying to grab him. But that wasn't the worst part, as he began writing in his diaries.

November 6, 1931Edit

Those hands attempted to grab me, trying to bring them with me, where... I buried them in that dark descent. The monsters wanted me down with them! I saw hundreds, if not thousands of those hands twisting and trying to grab me.

Strange occurrences began to unravel as William began to see visions of the deceased, decomposing corpses in the river. They were saying, “You know what you did,” and, “You're going to get it Billy Boy!!!” He began to yell back at them, saying they were not real and they were all a part of his stress. Then, he grabbed his pistol and began shooting it in the water and waving it with so little precaution. He made this almost a ceremony, where he would be tormented by the river, as if to jump into the river and become one of the men. This happened until that fateful night of November 9, 1931.

The same ritual continued as William began his taunting with the river, which was like some sort of driving force between the man and mother nature. Then, driving up in the Plymouth, James came along, seeing what was wrong with William and his strange behavioral changes which were so sudden. He knew that his brother was crazy, but insane? That's when he heard the gunshots in the distance, and wondered what was going on. That's where he found William next to a huge, gaping hole, where he supposedly buried Betty. He began yelling at the river again, saying where she was. There was nothing in the hole but some cloth covered in a small pool of dried up blood. This is when James said, there was nothing there. But William said, it was by the big oak tree which was standing in awe in front of the men. Then William collapsed in fate as life around him soon unraveled.

They laid there for a few more hours, when they began hearing the sirens of a police car. “Shit the fuzz found us,” James said as he picked up William, who was still in shock, and threw him in the front seat of the car. That's when James began to take off, shifting the gears at an unreasonable rate. After that, William woke out of his shock and began mumbling what time it was, James said around midnight. The cops began to catch up to the struggling Plymouth. Then, looking out of the side of his car, William began seeing the silhouette of a woman at the side of the road. She was just staring at them, time and time again he kept seeing the woman covered in leaves and vines, similar to the old riparian trees native to the Calaveras. His head began to hurt more and more until he couldn't think anymore, shouting, “Betty, she's alive!!!”

She shouted at them saying, “We will be reunited soon, my love,” looking mad at her decomposing face.

At that moment, James took a sharp turn on Eight Mile Road, approaching the sharp turn he made look easy many times before, when a silhouette of a woman appeared in the middle of the turn. But it was not Betty, it was this grotesque woman that was in an all-white dress with rows of sharp teeth, black soulless eyes, and a evil grin upon its face. William, out of pure shock turned the wheel to the right, into the opposite side facing the river. This happened against his brother's will and James began pushing him out of the way, but it was too late.

Then a large splash occurred as the speedy Plymouth crashed into the small river. The authorities stopped at the turn and began looking for the remains of the two young me, a manhunt was on its way. The car was eventually found a few hours later. Right next to it was James, coughing up water and trying to get away. However, he was captured and put in police custody later. However, the body of William Gregory was never found. An extensive search was put upon the river, looking for the two men. All they found were corpses by the river which the boys threw, tied to the cement blocks, along with a dress which resembled Betty’s over by the dump site, many of them looking like they had been tampered with while underwater, as if they had been eaten by maggots.

At James’s trial in 1933, he was practically guilty right as he was brought into the courthouse. Homicide, rum running, and a dozen other charges also, he was sentenced to life in prison with no way of parole. He spent the next three years in prison writing extensively about his brother, his prostitute of a girlfriend, and how insane his brother was, in extreme detail. After a bad night in prison, he began to hear voices in his head and began banging his head on the cold jail walls. Then, in 1936, after three years in jail he hung himself in his cell, leaving a note which said, “They wanted me to do it, the men in the river, the skulls, the Calaveras.” He also gave away in his suicide note the hideout's location, which was only a few miles downriver from the dumpsite.

After James gave away the hideout's location, an extensive search eventually led to the boys house where they found the diary. Also uncovered were the young man, and the details of rum running, their hitman activities, and the killing methods they used which spanned from as early as 1929. William was pronounced dead at the scene on November 9, 1931. The cause was unknown, and the bodies of Betty Dupree was never found.

This story has been passed down in local California Valley folklore for generations and is often heard through word of mouth from older people, who were working around the case when it happened, leaving some details lost or even forgotten. It also didn't help when the closest living relative of the Gregory brothers received the journal from the police, which she burned days later, leaving no sign of hard evidence behind. Most of the stuff from William's diary was written down from the behavior of James, or from witnesses explaining what was happening those cold nights.

To this day, there are still old legends saying that the Gregory Boys and their victims haunt the old riparian forests around the Calaveras River. For those who do not know, Calaveras means “skull” in the Spanish translation. This was due to a local Spanish explorer who found skulls of dead Native Americans, who were in conflict with the Spanish in colonial times, often slaughtering hundreds of people of all ages. Hundreds of years later, which many years later was the same area of the river where the Gregory boys buried the dead of their victims.

It is also said that if you go to the banks of the river you can almost hear a faint scream, as if someone is in the river being dragged down by a cement block. Others say that if you go on the day the boys died, that the headlights of the old Plymouth will follow you, with voices telling you to turn left into the river, only to disappear moments later. The final haunting involves Betty, who is dressed in all white and often called, “The Woman in White,” by some locals. According to legend, she stays by the road and lures unsuspecting drivers over to the stretch of road where the Gregory boys were found. Others say, on the night she was murdered you can still hear the muffled screams of a woman, followed by six gunshots.

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