Rum Runners of Eight Mile Road

Rum Runner on the Calaveras River

You probably have never heard of the Rum Runners in California’s Central Valley during the 1930’s. It is quite a puzzling urban legend that surrounds 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 in the United States. Of the areas in the United States that were often hit hard by bad times. The Central Valley was one of the typical cities hit by depression: High unemployment, lots of bums 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, east of a large inland port city.

Although many were captured by the police for rum running due to the lack of speed in their cars, the Gregory boys were and exception due to James, which was a skilled driver, and his trusty Plymouth 30U Coupe which could outrun any of the outdated and underpowered police cars of the day.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 walnuts near impossible. James pulled off a daring escape by turning a hard right to avoid turning into the Calaveras River. It was pretty practical, lead cops to curve, then take a hard right. They only used this method when carrying large quantities of booze, hue to smaller loads being 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 hit men. At one point killing some of the local cronies which he used as a decoy because he wasn't driving quick enough.

They dumped the bodies of there 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 left many of the people in the area to turn the other way when it came to crime investigations and police involvement.

James and William often known as their other names were known as “Starch and Poison” often due to other brutality of their murders often giving their presumed killers 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 a 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.

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

September 3, 1931 “Betty is one of the smartest women in the world. She figured out a new way of tricking the fuzz into believing them 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 women. 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 women and burying her near the river bed. 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 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. When he looked back in the mirror it was just him. He wrote this in his journal explaining the situation:

September 6 1931 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 obscurities outside like “coward” and “monsters”. Then Betty waking up said for him to go to sleep and 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 at the sounds of water and dragging sounds.

Over and over again night and night he began hearing those dragging sounds going more and more mad and becoming more schizophrenic. He began punching trees out of anger trying to find whatever answer there was 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 river front.

Then later on a nice fall day Betty and William were on the river front having a nice picnic with a good bottle of fancy cider and some fresh sandwiches, when an argument began to come up 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 begin joking around when all of a sudden he saw a man just come out of the river. The man began walking slowly towards them. He pointed franticly at the river 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 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 blunt object. 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 an Betty said she was going to leave, William snapped and grabbed the bottle of cider and smashed it over Betty’s head missing. This didn't stop as Betty was still running in some heels. She began running through to the old riparian vegetation of oak trees and bushes and ran across the road into a walnut farm with William coming up the rear. She hid in a small shack hiding for only a few minutes with William slowly following behind. He began shouting, “They want you Betty” then paused and saying “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 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 started hitting her over and over again until the body was unrecognizable. He then out of a fit grabbed the body and ran over by the river dragging a lifeless Betty with him. He dug a large hole and threw the remains in it, close to where he dumped the bodies with cement.

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, 1931 I had to kill her, she was on to me. The men at the river wanted me to kill her so. I pulled 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. Only time will come when she will be with me. Then men in the river said it would happen. It will happen. It will 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 river several miles up the Calaveras to tell him what happened and the gruesome fate of Betty 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 skeptical 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. He thought it was all over. Just another day and that the stress was 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 covered in blood and dirt was Betty saying “We will be together, forever” over and over again. Then he had flashes about the river and the road at which he was going a vast 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.

Then several days later William began his body burying and killing again routine 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, hands began raising out of the water grabbing his feel, they looked like mangled remains of bone and vegetation being decomposed by the freshwater river. Then he saw more and more hundreds of decomposed hands trying to grab him. But that wasn't the worst part as he began writing in his diaries:

November 6, 1931 Those hands began grabbing me trying the bring them with me, where……I buried them in that dark decent. The monsters wanted me down with them! I saw hundreds if not thousands of them hands twisting and trying to grab me.

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

The same ritual continued as William began doing 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 was coming along seeing what was wrong with William and his strange behavioral changes which were so sudden. Thats when he heard the gunshots in the distance wondering of what was going on. Thats 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 to him 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 and began to go crazy.

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 which was still in shock and threw him in the front seat of the car. Thats when James began to take off shifting the gears at an unreasonable rate. Thats when William woke out of his shock and began mumbling what time it was. James said around 2. The cops began to catch up to the struggling Plymouth. Then looking out of the side of his car William began seeing the frame of a women at the side of the road. She was just staring at them over and over again he kept seeing the women 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”.

At that moment James took a sharp turn on eight mile approaching the sharp turn he made look easy many times before when a silhouette of a women appeared in the middle of the turn. But it was not Betty, I was this grotesque women that was in 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 right into the opposite side facing the river against his brothers will with James pushing him out of the way, but it was too late.

Then a large splash happened 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 men. 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 man. 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 by the dump site, many of them looking like they had been tampered with while underwater.

At James’s trial in 1933 he was practically guilty right as he was brought into the courthouse. Homicide, rum running, and a dozen charges later he was set for life in prison with no way of parole. He spent the next 3 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 writing 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 hideouts location which was only a few miles downriver from the dumpsite.

After James gave way the hideouts location an extensive search eventually led to the boys house where they found the diary and the young man and the details of rum running, their hit man activities, and the killing methods they used which spanned from as early as 1929. The case was closed with no sign of William. William was pronounced dead at the scene on November 9, 1931. The cause was reasons unknown and the bodies of Betty Dupree and William Gregory were 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 which were working with or around the case when it happened leaving it to be that some details might have been 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 it days later leaving no sign of hard evidence for the story. Most of the stuff from Williams diary was written down from the memory 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 which were in conflict with the Spanish in colonial times. Which hundreds of years later was the same 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. Other’s say that if you go on the day the boys died that the headlights of the old Plymouth will follow you telling you to turn left into the river and then disappear. The final one is of Betty, which is dressed in all white and often called “The Women in White” by some locals. According to legend she stays by the road and lures unsuspecting drivers over the road where the Gregory boys were found. Other say on the night she was murdered you can still hear the muffled screams of a women followed by six gun shots.