Solved Murders - True Crime Stories - The Dark Story of Gary Simmons From Hidden Fantasies to Murder and Betrayal PART3 #36

Episode Date: October 22, 2025

#horrorstories #reddithorrorstories #ScaryStories #creepypasta #horrortales #truecrimehorror #murderanddeceit #darkfantasyturnshorror #chillingbetrayal #realcrimeencounters  The Dark Story of Gary Simmons – Part 3 delves deeper into the shocking true events of betrayal and murder. This installment exposes the final consequences of twisted fantasies, highlighting the dark psychology behind heinous acts and the terrifying reality of true crime that leaves lasting scars.  horrorstories, reddithorrorstories, scarystories, horrorstory, creepypasta, horrortales, garysimmonscrime, truecrimehorrorstories, murderandbetrayal, chillingrealstories, darkfantasyturnshorror, twistedtrueevents, realnightmarefuel, shockingtruecrime, manipulationsandfear, eerieencounters, hauntingtrueevents, dangerouschoices, realcriminaltales, truecrimefear

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It's late at night in the sticky heat of August, somewhere deep in Missouri. The kind of night where the air feels heavy, like even the cicadas are tired of singing. There's a swamp nearby, dark water swallowing reflections of the moon, frogs croaking in the reeds. A car pulls up to a small, isolated house. The place sits right on the edge of the swamp, looking almost a band. No light glows in the windows, the porch is completely dark. Inside that car are two people. Jeffrey Lee Wolf, 21 years old, hardworking, kind, adventurous, and next to him, his brand new girlfriend, Charlene Brooke, Leaser, only 18, still practically a kid, full of hope and nerves.

They've only been together a short while, but to them, it feels like forever. When they pull into the driveway, Brooke notices immediately, no porch light. It's eerie, unsettling. But Jeffrey doesn't hesitate. He knows this house. He knows the people inside. At least he thinks he does. They walk up the steps in the dark. In the center of the porch, a man is waiting. He's older, serious looking. His expression shifts when he spots Jeffrey. Suddenly, he's smiling like an old friend. and Jeffrey clearly knows him. He greets the man with casual confidence, as if everything's perfectly normal. Brooke, though, she can't shake the weirdness.

The man talks softly, almost whispering. At first, she thinks it's just because it's late. He doesn't want to wake neighbors. But something about his tone makes her uneasy, like he's trying to keep secrets from the night itself. They step inside. The house smells faintly of beer and swamp water. In the kitchen, the older man pulls out some bottles. He cracks them open, hands one to Jeffrey.

The two guys sit, talking, joking, swapping stories. Brooke sits at the table, trying to relax, but her stomach's tight. She doesn't know these people, doesn't know this place. And when you're 18, far from home, everything feels amplified. Every strange detail lingers. Minutes pass. everything seems calm. Too calm. Then, out of nowhere, a second man appears. No warning, no sound. Just bam, he's there, stepping into the room like a shadow. And before Brooke can even process what's happening, the gunshot rips the night apart. Jeffrey jerks violently, blood spraying. The room erupts in chaos. Brooke's ears ring, her heart leaps into her throat. She doesn't scram, she can't, the shock paralyzes her. The man with the gun, gone in an instant, slipping back into the dark like a

ghost. The older man, the one Jeffrey trusted, grabs Brooke. His hands are rough, cold. She kicks, twists, but he's stronger. He ties her up quickly, like he's done this before, like he's practiced. and then he shoves her into a box. Not a metaphorical box, not a figure of speech, an actual wooden box. It's cramped, suffocating, pitch black. Brooke's chest heaves. She can barely move, barely breathe.

From inside, all she can do is listen. And what she hears is chaos. Voices shouting, heavy footsteps thundering back and forth. The sound of something, Someone, being dragged, muffled arguing, bangs against the walls. And then silence. Utter silence. For what feels like forever.

Finally, the lid creaks open. The older man's face hovers above her. His eyes are cold, calculating. He yanks her out, violates her, then tosses her back in like she's nothing, like she's cargo. The lid slams shut again. And then, just when she thinks she can't take it anymore, the phone starts ringing. Once, twice, again and again, loud, shrill, cutting through the silence.

Nobody answers. That's when Brooke realizes, the house is empty. Nobody's guarding her. Her heart kicks into overdrive. This is her chance. She pounds against the lid with everything she's got. It creaks, cracks, finally pops open. She scrambles out, her wrists raw from rope burns. In a frenzy, she fumbles

with knots, tears them loose, stumbles to a drawer, grabs the first knife she can find. Barefoot, trembling, she bolts through the... On the many days of Christmas, the Guinness Storehouse brings to thee, a visit filled with festivity. Experience a story of Ireland's most iconic beer in a stunning Christmas setting at the Guinness Storehouse. Enjoy seven floors of interactive exhibition. and finish your visit with brett taken views of Dublin City from the home of Guinness. Live entertainment, great memories and the gravity bur. My goodness is Christmas at the Guinness Storehouse. Book now at ginnestorehouse.com.

Get the facts. Be Drinkaware. Visit drinkaware.com. Hi, I'm Darren Marler. Host of the Weird Darkness podcast. I want to talk about the most important tool in my podcast belt. Sfreaker is the all-in-one platform that makes it easy to record, host, and distribute your show everywhere. from Apple Podcasts to Spotify. But the real game changer for me

was Spreeker's monetization. Spreaker offers dynamic ad insertion. That means you can automatically insert ads into your episodes. No editing required. And with Spreker's programmatic ads, they'll bring the ads to you and you get paid for every download.

This turned my podcasting hobby into a full-time career. Sprinker also has a premium subscription model where your most dedicated listeners can pay for bonus content or early access, adding another revenue stream to what you're already doing. And the best part, Spreaker grows with you.

Whether you're just starting out or running a full-blown podcast network, Spreker's powerful tools scale effortlessly as your show grows. So if you're ready to podcast like a pro and get paid while doing it, check out Spreaker.com. That's S-P-R-E-A-K-E-R.com. Front door. The night air slams into her lungs. She runs across the street, heart hammering,

and dives into the bushes. She crouches low, holding her breath, praying. A car pulls up. Headlights slice through the dark. It stops right in front of the house she's just escaped from. Brook freezes. The door opens. Outsteps the older man, the one who tied her up. He spots the open door, freaks out and rushes inside. Moments later, he comes storming out, wild-eyed. He knows she's gone. He jumps back into the car, peels out, and vanishes into the night. Brooke seizes the moment.

She bolts to a neighbor's house, banging on the door, begging for help. And within minutes, red and blue lights flood the street. Police swarm the house, guns drawn, flashlights sweeping. The man's name they discover is Gary Carl Simmons. And what really happened that night is darker than Brooke could have ever imagined. The Trap. Here's the twisted truth. Jeffrey wasn't just some random.

victim. He had history with Gary. See, Jeffrey had once been good friends with Timothy Milano, Lori's younger brother. They'd worked together, hung out, trusted each other. And Gary knew that. He also knew Jeffrey traveled constantly for work, always up for a road trip, always moving from one gig to the next. So Gary built a trap. He invited Jeffrey to the house, knowing full well he'd probably bring someone with him. But here's the catch. Gary didn't want to do this alone. That night, before Jeffrey ever showed up, Gary went to Lori's apartment.

He knew Timothy would be there, always protecting his sister. And Gary used that. He cornered Timothy, threatened him, told him straight up, Help me, or your sister and her kids die. Timothy was trapped. He had no choice. He followed Gary to the swamp house, loaded a gun, and when Jeffrey walked through the door, Timothy pulled the trigger. Nine times.

Nine bullets into a man he once called a friend. Jeffrey collapsed, bleeding out. His life ripped away in an instant. And Gary? Gary took it from there. He grabbed Brooke, tied her up, shoved her in the box. Then he turned his attention to Jeffrey's body. dragging it to the bathroom, Gary set to work.

What came next is gruesome, but it's the truth. He dismembered Jeffrey, methodical, detached, like he'd rehearsed it in his mind a thousand times, through his twisted stories. Piece by piece, he handed the remains to Timothy, and together they carried them out to the swamp. Timothy climbed into a boat, pushed off into the black water, and scattered Jeffrey's remains into the murky depths. By the time he returned, Gary had already locked Brooke away again. And that's when the phone started ringing. Those calls, they were Lori. From miles away,

Lori was dialing again and again, terrified, not realizing that her brother was knee-deep in Gary's horror show. Each unanswered call told Brooke she was alone, told her nobody was coming, until she found her own courage and escaped. Aftermath. When Gary realized Brooke had slipped away, he panicked. He jumped into his car, drove to a shopping center, and bought a videotape. Sat in front of a camera, confessed, sort of. Half-truths, cryptic admissions.

Like he wanted to control the narrative even then. And finally, he turned himself in. Both Gary and Timothy were arrested and charged with the capital murder of Jeffrey Wolf. But the nightmare didn't stop there. While awaiting trial, Gary tried to finish what he started. From his jail cell, he plotted Brooks' murder, tried to hire a hitman, wanted her silenced, erased. But the plan fell apart. Brooks survived. Physically at least, mentally, she would never be the same. Imagine being 18, watching your boyfriend murdered, being tied up, violated, locked in a box and barely escaping with your life.

Then imagine knowing that the man who did it still wanted you dead. Brooke lived in fear for decades. She dyed her hair, changed her appearance, moved constantly, always looking over her shoulder, never feeling safe. Trauma hung on her like a second skin. Justice, if you can call it that. It took a year before the trial began. On August 25th, 1997, Gary and Timothy finally faced justice.

The courtroom was heavy with tension. Brooke sat there. Hi, I'm Darren Marler. Host of the Weird Darkness podcast. I want to talk about the most important tool in my podcast belt. Spreaker is the all-in-one platform that makes it easy to record, host, and distribute your show everywhere. From Apple Podcasts to Spotify. But the real game changer for me was Spreaker's monetization.

Spreaker offers dynamic ad insertion. That means you can all. automatically insert ads into your episodes. No editing required. And with Spreaker's programmatic ads, they'll bring the ads to you, and you get paid for every download. This turned my podcasting hobby into a full-time career. Sprinker also has a premium subscription model

where your most dedicated listeners can pay for bonus content or early access, adding another revenue stream to what you're already doing. And the best part, Spreaker grows with you. Whether you're just starting out or running a full-blown podcast network, Spreeker's powerful tools scale effortlessly as your show grows. So if you're ready to podcast like a pro and get paid while doing it, check out spreeker.com. That's S-P-R-E-A-K-E-R dot com. Fragile but unbroken, staring down the man who had tried to destroy her. On August 28th, the verdict came. Gary Simmons, guilty of capital murder, guilty of kidnapping, guilty of holding

Brooke captive. Timothy Milano, guilty of firing the bullets that killed Jeffrey Wolfe. Timothy was sentenced to life in prison without parole. Gary, he got the death penalty. And after years of appeals, stalling, and courtroom drama, the sentence was carried out on June 20, 2012. Gary Carl Simmons was executed. But here's the thing about trauma. Killing the monster doesn't Erase the side.