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Serial Killers

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Confessions and Unsolved Mysteries

From The Missing Candy Heiress and the Chicago Horse MafiaJun 29, 2026

Excerpt from Serial Killers

The Missing Candy Heiress and the Chicago Horse MafiaJun 29, 2026 — starts at 0:00

You know the old saying, it's like finding a needle in a haystack When someone goes missing There's usually a police report an investigation piecing together a timeline, collecting evidence, interviewing witnesses all the trappings of a traditional crime story The thing about disappearances is there's no guarantee that Cime actually occurred Wh makes finding answers Comlicated Because the missing person could be lost kidned Dead O maybe They just ran away. went into hiding and don't want to be found O maybe That's what they're abductors Want you to think It's often hard to tell And investigations can get even more complicated when the person officials are trying to find has money to burn Like in today's story. When a multimillionaire heiress disappears, a near endless supply of resources means they could be Almost anywhere in the world One person in a sea. millions Statistically It makes finding a needle in a haystack Se easy I'm Harvey Gan And this is Killer Stories. There are certain parts of Helen Brack's life that sound like a fairy tale. For example, she started as a coal miner's daughter, born in rural Ohio, but after moving to Florida, she started working at a country club, where she casually IL, met her future husband, a man who just so happened to be the heir to a very large fortune and not just any fortune, a candy fortune. sweet And if there are any candy tycoons out there tuning in, my DM's are open. and single. So I love sweets. Anyway, Helen meets this candy man named Frank And the second fring puts a ring on it. Helen becomes a multimillionaire And one of the richest women in America Frank and Helen buildt a big house on an island in Florida. One house turns to two with an eighteen room mansion in a Chicago suburb. called Glenview close to their literal candy factory, which in my mind looks like Willy Wonka's, even though I know it probably doesn't, let me have this for one second Helen It's safe to say, Helen loves her life She's the eccentric kind of rich, and she's good at it. She loves collecting luxury cars and painting them pastel pink and lavender She loves food but prefers takeout chicken to fancy dining And I don't know if you've ever heard of automatic writing before, but it's basically stream of conscious writing When Helen does it, she says she follows the psychic force that's guiding her hands She's a little cooky. And she does some good things with her money too like supporting charities that help animals because another thing about Helen is she loves animals Eespecially dogs and Horses By february nineteen seventy seven, Helen's sixty five years old and her husband Frank. is dead Helen's a widow And she has at least one man in her life His name is Jack Matlick. And he's Helen's House man whichich is a word I've never heard of before researching this story So you're welcome But Jack basically acts as Helen's Butler pllus He manages the household, fixes whatever breaks, runs errands, and acts as Helen's personal chauffeur ust be nice On the seventeenth of February, Helen goes to the Mayo Clinic in Minnesota. It's one of the best in the country and Helen has to pull some strings to be seen, but Her friend, Richard Bailey, helps her jump the line and gets an appointment for a full physical After a week long visit with some of America's top doctors, the news is good Helen is an excellent health So, when she leaves the clinic, she stops at the gift shop because why not? And if it were any other day, such a casual drop in would be completely unmemorable for Helen We wouldn't even be talking about it, but the reason we are talking about it is because It's the last place she's seen before she disappears And that gives everything Helen does in this gift shop Any of it matters or not It's all we have The salesperson who helps Helen in the store later says that she seems like she was in a rush. taps her foot impatiently as she's checking out. and when the employee apologizes for the weaight, Helen apparently says she's in a hurry and her house manan Jack is waiting for her which is only notable because It's not true Helen's next stop is the airport She has a plane ticket back to Chicago. Jack is supposed to pick her up hair. Like I said, it could be nothing, a slip of the tongue, an exaggeration or a lie to excuse her impatience Or It could be something more Whatever the case Those are the last words Ellen says before she disappears. In a hurry My house then is waiting for me. If things played out as expected Helen would have taken a cab to the airport after she left and she would have boarded her schedule flight The problem is We don't know if either one happened Here's what we do know Almost two weeks go by before Helen's houseman Jack, tries to report her missing to police And you're probably thinking, that's a lot of time. Why wasn't there more concern when Helen didn't show up at the airport when she was supposed to? Well, according to Jack Tell him did show up that day She landed at O'Hare, as expected He drove her back to the mansion in Glenview, and she spent the next four days at home access, things were mostly Uneventful Helen laid low, but there are four things that stand out in his account of things. One. He says Helen accidentally hurt her hand When she slammed a car trunk shut. Tw Jack and Helen got into a small fight because Jack sold a car she gifted him in order to pay off some gambling debts Three Helen went on a date with some man who Jack Iidn't know And four Helen signed a stack of checks for Jack to deliver to her bank She wanted to get her finances in order before she left. on another trip. Helen had recently bought a condo in Fort Lauderdale, and she was going down to decorate it Jack says he dropped Helen off at O'Hare shortly before seven AM on february twenty first He assumed everything was fine He didn't hear from Helen that week. which was unusual. So he called her friends down in Florida and was surprised to learn No one Cats seen her notot even her building manager. That's when Jack decided to go to the police in Glenview. which would all make some sense if Jack is telling the truth There are a few red flags in his account. For example There really isn't anything or anyone who can corroborate whether Helen even returned from her trip to the Molinic Investigators later try and find the cab driver who took her to the airport after she visited the gift shop best they can find is a man who says It's Possible he drove Helen that day but he can't remember There's a similar problem with the airport and plane staff. They can't remember whether they saw Helen on board the flight or not Her ticket was used This is the nineteen seventies, insecurity is lax. They often didn't check IDs for domestic flights So There's no way to know if it was actually Helen who boarded the plane And then there's Helen's four day stay at her mansion in Glenview Jack says she went on a date with a man while she was there. but If she did, Investigators never find that person In fact, they don't find anyone who actually spoke to Helen in those four days. Which is strange because Helen was a social person who loved to talk on the phone and a few friends called her that weekend but they only ever got the chance with J Each time he picked up the phone and told them Helen was unavailable Which again, could be nothing, but I don't know, sure seems suspicious to me And I haven't even gone to the part where Jack burns Helen's private papers. Or orders A meat grinder This episode is brought to you by Chime Chime is doing banking a bit differently It's fee free banking designed for you. No monthly fees, no overdraft traps and thousands of fee free ATMs. Plus, there's a bunch of benefits like earning five percent cash back on your Chime card in a chosen category. Chime is not just smarter banking. It is the most rewarding way to bank. Join the millions who are already banking fee free today He to chime. com slash killers. It only takes a few minutes to sign up Chime is a FintTech not a bank. Banking services for Chime card provided by Chime's bank partners. Optional products and services may have fees or charges, state annual percentage yield and cash back for Chime Prime only. No minimum balance required. For more information on APY rates, My pay, Sot mee and travel perks go to chime d. com slash disclosures. This episode is brought you by WSS There's something about soccer fandom that feels inherited One generation passes it down to the next, the rivalries, the rituals, the jerseys that mean everything And when it's finally time to gear up for match dayay WSS has the whole squad covered. From official soccer jerseys and gear to sportswear, sneakers and more, WSS has the best value on everything your family needs Shop now at your local WSS or online at allyourmagic. com Let's talk about a condition many people haven't heard of And it turns out, it's more common than you'd think Heyrony's disisease, or PD for short PD can happen when scar tissue builds up under the skin of the penis This can cause a curve or a bump during an erection and for some men, lead to pain during intimacy and may impact mental health It may also lead to anger and frustration, depression, lower self esteem and even withdraw from sexual activity and physical intimacy Because of this, some men could feel embarrassed or reluctant to talk about PD The actual cause of PD isn't always known In some cases, it may be linked to a minor injury or repeated injuries during sex or other physical activity The good news is PD is treatable If you notice a curve with a bump, a trusted urology specialist can help diagnose it and walk you through your options, including non surgical treatment. To learn more about Pironi's disease, visit talkaboutpd. com. So I told you, Helen Brack's houseman Jack Matlick tries to report her missing to Glenview Police on march fourth, nineteen seventy seven. Something weird happens when he does The police tell him He can't file a report For some reason they say it has to come from a family member, which makes things a little difficult because Helen doesn't have much family Her husband and parents are all gone Her next of kin is her brother Charles. Charles still lives in rural Ohio, and while Helen has been generous to her brother over the years They've never been close When Jack tells Charles that Helen hasn't been seen for a while He agrees to fly to Chicago as soon as possible to report his sister missing. Meanwhile, Jack also contacts Helen's financial manager A guy named Everet Moore Everet's much less concerned by the news. He basically says, it's none of Jack's business where Helen is and that she has no obligation to tell Jack anything Which sounds like some class dynamics to me. In the end, Evet agrees to meet at Helen's house the next morning to talk And what follows is a very strange series of events. Et arrives at Helen's house before Charles. and one of the first things Jack does is lead him to Helen's bedroom and show him a dresser drawer filled with Helen's private papers Journals, automatic writing, lots of stuff that could be valuable to a missing person's investigation. But Jad doesn't want to play detective with Everett He wants to burn the papers He says Helen told him to burn them should anything happen to her whichich is a weird thing to say considering presumably No one knows what happened to Helen at this point What's even stranger is When Helen's brother Charles arrives He also wants to brand the papers He claims he doesn't want Helen's private life splashed all over the news I told you about Helen's psychic free wrriting Charles knows his sister was interested in the occult. doesn't want a press league to hurt her reputation. So Charles helpels Jack burn ers whatever secrets they held quite literally up in flames. And when they're finally done They decide Okay And now we can report her missing. So I've told you some of what police find when they try to corroborate Jack's account of things How they can't verify whether she actually took a cab to the airport or boarded her plane and how Helen's friends tried to reach her at her mansion, but Jack always picked up and said She was busy But that's not all phone records show Jack made some outgoing phone calls during that time period And to say that they're concerning be an understatement One call was Jack hiring people to repaint two rooms in the house and replace a rug. as soon as possible. and another was to place a rush order from a department store for a meat grinder I know this man's job was to take care of the house, which probably included renovations and making sure the kitchen was stocked. Theoretically could be a coincidence Why would Helen N a meat grinder rush to the house if she was about to fly to Florida What's more, there are parts of Jack's story that can easily be proven false. Like how he said he got into a fight with Helen over a car he sold He never sold that car. And those checks Helen supposedly signed Two of them were for Jack but none of them were written by Helen. writing looks nothing like hers. Jack says it's because Helen Hurt her hand Hwriting experts says There's no way injury or not Helen didnn't write the checks And while we don't know if Helen got on a plane back to Chicago, she almost certainly didn't fly to Florida told police, he dropped Helen off at seven AM There weren't even flights to Florida before ten that day there's no way Helen would have gotten there so early. This is long before security lines and widespread travel anxiety. Plus, the airline tells police confident Helen never boarded a plane that day Nor did she land in Fort Lauderdale begs the question Why would chat Ly Police aren't sure Because as strange as all those fictional details are, They don't really add up to anything. The meat grinder. It sounds way worse than it is Police learn, it's basically It's just a small blender attachment that could never help dispose of a body then there's the workers hired to clean and repaint the house. They say they didn't notice anything unusual when they were there And if they were there to clean up a crime scene, they'd probably notice something Investigators have no idea why Jack would lie about selling his car It just doesn't make sense And as for the handwriting on those checks, it might not be Helen's. but It's not Jack's either which is just so confusing There's all this evidence to prove that Jack is a liar, but Why lie Given Helen's enormous wealth, investigators try to dig into her finances. Maybe there's something or someone in her will that could point them in a direction But Helen's lawyer stonewalls the police He won't release her will because of attorney client privilege He says not while she could still be alive which is normal Guy still doesn't budge. after a court orders him to hand over the will, he gets charged with contempt of court And still He does nothing. Why I have no idea To to the best of my knowledge, he's never spoken publicly about it. My guess is it has something to do with Helen's incredible wealth I doubt he would do or act the same way for just any other client But this is Chicago's candy lady, one of the richest women in the country. There's a lot at stake for every single person connected to this case which kind of makes them all A little suspicious Without access to Helen's will, investigators make some educated guesses about who stands to benefit the most from her death There's her brother, Charles, but he has an airtight alibi He was in Ohio the whole time Then there's Helen's charities, but That doesn't feel right The only person police can think of is Helen's good friend. Richard Bailey He's the guy who helped Helen get into the Mayo Clinic before she disappeared And depending on who you ask He's more than Helen's friend If you know what I mean, Pz. her much younger Lover with an almost twenty year age gap Richer dresses and flashy clothes drives expensive cars and owns a fleet of horses. Unlike Helen It's a little unclear where his money comes from. Except For maybe his habit of serrely dating older wealthy widows Evening by his remorse Buy a new car I'll be moving in Let's get started. Sorry, I think there's been a mistake. I bought it from Carvana. You what? Yeah, great price. I even' have seven days to love it or return it. So there's no No, no buyer's remorse. More like buyers rejoice? I guuess I'll let myself out. Congratulations. I mean it. Buyers rejoice. Buy your car today on Carbana. Limitations exlusions may apply Si here sevayurn policy at cararbona d Hey parents How do you make smarter choices for your kids college today? That's where Sally can help With Sally, you can find scholarships, funding options, tools, and guidance all in one place And if you need a loan, Sally has options for different families and different situations College is only worth it if you do it right. So don't just help your kid go. Help them go smarter Sally d. com slash go parents Let's talk about Pay Roni's disease, or PD It's not widely talked about. and some men may feel reluctant to bring it up But it's more common than you'd think PD can happen when scar tissue builds up under the skin of the penis, causing a curve or a bump during an erection that for some men, may lead to pain during intimacy and impact mental health A trusted urology specialist can help diagnose PD and walk you through your options, including non surgical treatment Visit talkaboutpD. com Police home in on two primary suspects in Helen Brack's disappearance Her house manan, Jack Matlick and her friend and possible lover Richard Bailey. Jack has proven himself to be a liar And Richer reeks of sleeves His type is rich older widows. And the more zeros in their bank accounts the better Investigators are confident he's a con artist, but the challenge is connecting Richard to Helen's disappearance and without knowing the contents of her will They don't know if Richard stood to benefit more from Helen living O dead So All progress stalls in Helen's case And that eventually goes cold After enough time passes, Helen's lawyer rethinks his decision to withhold her will He hands it over to the police who think it's finally going to be their big break changes almost Nothing Kelen planned to leave about half a million dollars to her brother Charles fifty thousand dollars to Jack The rest Almost all of it is supposed to go to establish a foundation in her name nineteen point five million dollars all to improve the welfare of animals. None of it feels new or surprising, so the case Stays cold A enough time passes Helen is declared L legally All that money gets dispersed Acept. Jack doesn't receive his share Helen's estate sues him for a bunch of things, including delivering those forged checks to the bank. He agrees to forfeit the fifty thousand if the estate drops all charges against him which They do After that, Jack moves to Pennsylvania and tries to live a quiet life with his family He wants to put the past behind him, but some characters in this story aren't so quick to change Richard, for example, never stopped dating wealthy widows And eventually proves the police right You know the old saying? If it looks like a horse, smells like a horse, and nighays like a horse, it probably has a horse size cannot say that. Okay, then I won' The pointoint is Richard looked, smelled and sounded like a con artist because He was a con artist Cught up in a horse mafia That's right, a horse mafat now. What is a horse mafia? Well, I'm glad you asked. Richard dated wealthy widows so he could sell them and their rich friends, horses at exorbitant prices. He would pitch it as a great investment. you know, like the horse could compete in shows or races and win them considerable money. But what he was actually selling Fantasy Now there's no such thing as a bad horse. All horses are good and worthy But Richard wasn't selling prized deeds horses weren't about to win anything They didn't have any pedigree that would mean something in that world and many of them had undisclosed illnesses So the women were unknowingly doing charity work. Bus And Richard wasn't just charging for the horses themselves. That was just a gateway to other income streams. Richard operated within a loose conglomerate of horse buyers, sellers, stable owners, vets and other associates, and they all profited off the facade build together It's literally been called the Chicago Horse Mafia. I wasn't joking about that. And Richard and his friends would keep throwing expenses at these women until they literally left some of their victims complepletely penniless Any of that have to do with Helen Well, over time, a bunch of Richard's victims file civil suits against him And in nineteen eighty nine, they end up attracting the attention of the assistant US attorney Stephven Miller. Nope, not that Stephven Miller, who's currently serving in the White House iff different one Anyway, it's been over a decade since Helen disappeared, but even still, Helen is the whole reason a big wig attorney like Stephven is interested in the relatively small time lawsuits. He thinks he could possibly connect Helen to the horse ring and in doing so connects Richard to her disappearance and solve this case once and for all An initial connection proves to be easy Stephven learns that Helen bought three horses from Richard's brother in nineteen seventy five two years before she disappeared Richard's brother then split the one hundred thousand dollars Helen paid for them with Richard Which is a lot of profit considering the brothers paid less than twenty thousand to buy those same horses o connect Richard to Helen's disappearance, Stephven needs to find a motive a reason why Richard would have wanted her out of the picture Like if she found out She was being swindled all the wealthy women Richard rubbed elbows with, Helen was probably the most influential. If she knew about his scheme, she could really get him in trouble. So Stephven pursues that theory. And it leads him to one of Helen's close friends William. Cats By the time Stehven's digging around, William is dead William's brother is alive And he tells Stehven that Helen did know about the horse scamp She opened up to William about it right before she visited the Mayo Clinic, and William referred Helen to one of his friends in the state attorney's office, so she could do something about it It's the exact information Stehven's looking for. theory about Helen's disappearance seems to be Right on the money But Stephven continues building his case Richard couldn't have kidnapped or killed Helen himself. Richher was in Florida when she disappeared, and as I mentioned, Helen never made it to Florida So Stehven starts looking for possible accomplices And he learns there's no shortage. Crooked and dangerous men in the horse mafia Like Silas Jane Silas did business with Richard and famously resorted to violence to protect his business. He killed his own brother in front of his family just because his brother tried to become petitor. So imagine what he might have done If he found out Then there's Joe Edward Clemens, another crook, an associate of Richard's. Stephen learns he's currently in jail for selling a horse that didn't exist So, Stehven pays him a visit hoping that maybe he'll talk in exchange for a lighter sentence And what do you know? Joe has an enlightening story tell He tells Stehven that back in february nineteen seventy seven He met up with a Richard Bailey And over lunch, Richard told them that he was in trouble with Candy lady A K A Helen Richard apparently said he needed someone take care of the situation which was a request that was understood everyone at the table But Joe claims that he turned the job down. partartly because he wasn't a contract killer Partly because Richher wasn't offering enough money It's not the smoking gun Stehven needs, but it's something gets Joe's statement on record showing that Richard was soliciting Helen's murder. He's never able to confirm if anyone ever carried In nineteen ninety four, now seventeen years after her disappearance, Stephven decides to take his findings to court He brings twenty nine counts against Richard Bailey The vast majority are fraud or conspiracy related, but they also include soliciting Helen Brack's murder Richard pleads guilty to sixteen of the counts, but none connected to Helen's death By taking the plea deal, Richard avoids a trial and the murder related charges are dropped He's handed thirty years in prison for fraud, racketeering, and money laundering And the judge that orders the sentence tells Richard He's lucky, it's not more Because in his opinion Evidence clearly shows he conspired to murder Helen But Richard goes to prison with an incomplete picture. actually happen And nothing changes until Another decade passes. In two thousand five, Joe Clemens, the guy who said he turned down the contract to kill Helen, goes public. With another story He says Silas Jane the hit on Helen And he recruited a team of seven men and one woman to help him Remember at the gift shop when Helen said her house manan was waiting for her Well, apparently He was Silas hired Jack Matlick to help carry out the murder Jack met Helen in Minnesota outside the Mayo Clinic The woman Syas hired Flew with Helen's plane ticket to Chicago while Jack and Helen Drove. When Helen got back to Glenview, the men When it seemed like she was still alive, Joe says He finished the job himself. two blank Jack had the house clean and repainted just to be safe The other men took Helly's body to a steel mill in Indiana wear They incinerated it The show swears Richard Bailey really did solicit Helen's murder first. In the end, he says Richard didn't lead the plot to kill her Silas took on that task Once he found out what Helen knew And there's a lot about Joe's statement that adds up. makes the different pieces make sense Imly time Joe is saying any of this. There really isn't anyone around to croborate in. Everyone's either dead. or in prison for other crimes And he only gives the statement after he's granted immunity So It doesn't lead to any convictions And like so much of this case still has to be taken with a grain of salt. Helen Brack's disappearance and death is still officially Unsved evenven if it feels soft And there's been no real justice for what happened to her Whatever that is Finding a needle in a haystack is hard

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