Killer Stories with Harvey Guillén - The Missing Candy Heiress and the Chicago Horse Mafia

Episode Date: June 29, 2026

In 1977, candy heiress Helen Brach – one of the richest women in America – vanishes. Detectives consider the many people who might have wanted to get their hands on her money. Ultimately, the primary suspect that emerges is… the Chicago horse mafia. Sources for this episode include: Hot Blood: The True Story of an Heiress, a Gigolo, and a Shocking Murder by Ken Englade“The Puzzle That’s Missing One Piece” (WashPo)“Candy Heiress's Murder Probe Exposes Brutality in Horse World” (LA Times) Keep up with Killer Stories! Instagram: @killerstoriespodTikTok: @killerstoriespodX: @killerstorieshq Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. But the thing about disappearances is there's no guarantee that a crime actually occurred, which makes finding answers complicated. Because the missing person could be lost, kidnapped, dead. Or maybe they just ran away, went into hiding and don't want to be found.

Or maybe that's what their 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 bribe. burn. Like in today's story, when a multi-millionaire heiress disappears, a near endless supply of resources means they could be almost anywhere in the world. One person in a sea of millions. Statistically, they mix finding a needle in a haystack. Seem easy. I'm Harvey Guillen, and this is killer stories.

There are certain parts of Helen Brax'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, IRL, 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 DMs are open. And I'm single. So I love sweets. Anyway, Helen meets this candy man named Frank.

And the second Frank puts a ring on it, Helen becomes a multi-millionaire. And one of the richest women in America, Frank and Helen built a big house on an island in Florida. One house turns to two with an 18-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. But 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 hand. She's a little cookie. 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, especially dogs and horses. By February 1977, Helen's 65 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 houseman, which is a word I've never heard of before researching this story. So, you're welcome. But Jack basically acts as Helen's butler plus.

He manages the household, fixes whatever breaks, runs errands, and acts as Helen's personal chauffeur. Must be nice. On the 17th 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 a 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, wait. Whether 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. She taps her foot impatiently as she's checking out,

and when the employee apologizes for the wait, Helen apparently says she's in a hurry, and her houseman, 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 at O'Hare. 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 Helen says before she disappears. I'm in a hurry. my houseman 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. and why wasn't there more concern when Helen didn't show up at the airport when she was supposed to? Well, according to Jack, Helen 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. Jack says 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. Two, 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 didn'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 decorated. Jack says he dropped Helen off at O'Hare shortly before 7 a.m. on February 21st. He assumed everything was fine, but 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 had seen her.

Not even her building manager. And that's when Jack decided to go to the police in Glenview. Which would all make some sense if Jack is telling the truth, but 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 Mayo Clinic. Investigators later tried and find the cab driver who took her to the airport after she visited the gift shop.

But the 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 board the flight or not. Her ticket was used, but this is the 1970s. Insecurity is lax. They often didn't check IDs for domestic flights.

So there's no way to know if it's. 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 to speak

with Jack. 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. In Toronto, every arrival is a statement, and nothing says it better than this. Cadillac Optic was the number one selling luxury EV in Canada for 2025. Find your rhythm across a seamless 33-inch display and an immersive 19-speaker AKG surround audio system. This city demands agility, and Optic delivers with precision to make every drive extraordinary. Let's take the Cadillac.

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Listen now wherever you get your podcasts. So I told you Helen Bragg's houseman, Jack Matlick, tries to report her missing to Glenview Police on March 4, 1977. But 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 Everett Moore. Everett'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. But in the end, Everett agrees to meet at Helen's house the next morning to talk. And what follows is a very strange series of events. Everett 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 Jack doesn't want to play detective with Everett. He wants to burn the papers. He says Helen told him to burn them should anything happened to her, which is a weird thing to say, considering presumably no one knows what happened to Helen at this point. But what's even stranger is, when Helen's brother Charles arrives, he also wants to burn 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 writing. Charles knows his sister was interested in the occult,

and he doesn't want a press leak to hurt her reputation. So Charles helps Jack burn the paper. Whatever secrets they held, quite literally go up in flames. And when they're finally done, they decide, okay, 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 would 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. And I know this man's job was to take care of the house, which probably included renovations and making sure the kitchen was stocked, so it theoretically could be a coincidence,

but why would Helen need 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. The handwriting looks nothing like hers.

Jack says it's because Helen hurt her hand. But a handwriting expert says there's no way. injury or not, Helen didn'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. Jack told police he dropped Helen off at 7 a.m. But there weren't even flights to Florida before 10 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 their confident Helen never boarded a plane that day, nor did she land in Fort Lauderdale, which begs the question, why would Jack lie? Police aren't sure, because as strange as all those fictional details are,

they don't really add up to anything, like the meat grinder. It sounds way worse than it is. Police learn it's basically just a source, 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. That just doesn't make

sense. And as for the handwriting on those checks, it might not be Helens. 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 tried to dig into her finances. Maybe there's something or someone in her will that could point them in a direction. But a 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.

But the 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 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. 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, he's her. much younger lover, with an almost 20-year age gap. Richard dresses in 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 serially dating older wealthy widows. Police home in on two primary sources. suspects in Helen Brax's disappearance. Her houseman, Jack Matlick, and her friend and possible lover,

Richard Bailey. Jack has proven himself to be a liar, and Richard 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 or dead. So, all progress stalls in Helen's case, and it 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. But it changes. changes almost nothing. Helen planned to leave about half a million dollars to her brother, Charles, $50,000 to Jack, but the rest, almost all of it is supposed to go to establish a foundation in her name. $19.5 million, all to improve the welfare of animals. None of it feels new or surprising, so the case stays cold.

And after enough time passes, Helen is declared legally dead. All that money gets dispersed, except 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 50,000 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 stops dating wealthy widows, and eventually he proves the police right. You know the old saying, if it looks like a horse, smells like a horse, and nays like a horse, it probably has a horse size.

What? I cannot say that. Well, then... Okay, then I won't. The point is, Richard looked, smelled, and sounded like a con artist because he was a con artist, caught up in a horse mafia.

That's right, a horse mafia. 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 was a fantasy. Now, there's no such thing as a bad horse. All horses are good and worthy. But Richard wasn't selling prize steeds. His 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, not business.

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 they built. 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 completely penniless. What does any of that have to do with Helen? Well, over time, a bunch of Richard's victims file civil suits against him. And in 1989,

they end up attracting the attention of the assistant U.S. attorney Stephen Miller. Nope, not that Stephen Miller who's currently serving in the White House. 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 Stephen 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 disappearing.

and solve his case once and for all. In initial connection proves to be easy. Stephen learns that Helen bought three horses from Richard's brother in 1975, two years before she disappeared. Richard's brother then split the $100,000 Helen paid for them with Richard, which is a lot of profit

considering the brothers paid less than $20,000 to buy those same horses. But to connect Richard to Helen's decision, disappearance, Stephen 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. Of 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, Stephen pursues that theory, and it leads him to one of Helen's close friends. William Cats.

By the time Stephen's digging around, William is dead. But William's brother is alive. And he tells Stephen that Helen did know about the horse scam. 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 Stephen's looking for. His theory about Helen's disappearance seems to be right on the money.

But Stephen continues building his case. Richard couldn't have kidnapped or killed Helen himself. Richard was in Florida when she disappeared, and as I mentioned, Helen never made it to Florida. So Stephen starts looking for possible accomplices. And he learns there's no shortage of 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 a competitor. So imagine what he might have done if he found out about Helen. Then there's Joe Edward Plymouth,

another crook and associate of Richards. Stephen learned he's currently in jail for selling a horse that didn't exist. So Stephen 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 to tell. He tells Stephen that back in February 1977, he met up with Richard Bailey. And over lunch, Richard told them that he was in trouble with the Candy Lady, aka Helen. Richard apparently said

he needed someone to take care of the situation, which was a request that was understood by everyone at the table. But Joe claims that he turned the job down, partly because he wasn't a contract killer, partly because Richard wasn't offering enough money. It's not the smoking gun Stephen needs,

but it's something. He gets Joe's statement on record showing that Richard was soliciting Helen's murder, but he's never able to confirm if anyone ever carried it out. In 1994, now 17 years after her disappearance, Stephen decides to take his findings to court. He brings 29 counts against Richard Bailey. The vast majority are fraud or conspiracy-related,

but they also include soliciting Helen Brax murder. Richard pleads guilty to 16. 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 30 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, the evidence clearly shows he conspired to murder Helen. But Richard, goes to prison with an incomplete picture of what actually happened, and nothing changes until another decade passes.

In 2005, Joe Plemence, the guy who said he turned down the contract to kill Helen, goes public with another story. He says Silas Jane let 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 houseman 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 Silas hired flew with Helen's plane ticket back to Chicago, while Jack and Helen drove. When Helen got back to Glenview, the men beat her. When it seemed like she was still alive, Joe says he finished the job himself with two point-blank bullets. Jack had the house clean and repainted just to be safe. The other men took Helen's body to a steel mill in Indiana, where they incinerated it. Joe swears Richard Bailey really did solicit Helen's murder first, but 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, that makes the different pieces make sense. But importantly, by the time Joe is saying

any of this, there really isn't anyone around to corroborate it. 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, it still has to be taken with a grain of salt. Helen Bragg's disappearance and death is still

officially unsolved, even if it feels solved. And there's been no real justice for what happened to her, whatever that is. Finding a needle in a haystack is hard. But eventually, you either find it or you don't. Finding the truth is messier. Especially when everyone involved has something to lose if it's ever uncovered. Thanks for tuning in to Killer Stories, a Spotify podcast, new episodes released on Mondays.

If you like today's story and want to learn more, we drop some of our favorite sources in the episode description. Until next time, I'm Harvey Gien. Stay safe out there.