The Thing About Helen & Olga - Ep. 3: Silk Pajamas and a Flimsy Nightgown 37:05

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Always Nightpads will do their up to 100% leak protection thing. Shop for Always in-store or online, wherever you get your pads. There are many methods for ridding oneself of people who have become, shall we say, inconvenient.

Here at Dateline, we've covered most of them. There are several tools available: guns, knives, poison, rope, you name it. Each has advantages and disadvantages, but nothing we've encountered matches the simple, no-frills efficiency of driving a one-and-a-half-ton car over someone down on the pavement.

And that, it seems, is exactly what happened not once, but twice in the back alleys of Los Angeles. Bodies were crushed and crumpled in alleys. This is very evil. The body was laying here with his head facing towards the south.

In this episode, you'll hear from the two elderly ladies at the heart of our story. I am insurance fraud. Yes. My partner, Halle Goley, had insurance, not me. Who has done this to me? This is inhuman. This is worse than Germany. And you'll hear what investigators found inside their apartments. The side table there, and sitting on the side table was a book, The Sociopath That Lives Next Door.

And we all looked at it and we just started laughing. I'm Keith Morrison, and this is episode three of Dateline's latest podcast, The Thing About Helen and Olga. What a lovely way to start a new year. 2006 had just begun, and Helen Golay and Olga Rudderschmidt were as pleased as punch. No wonder. New York Mutual told them they were sending a representative to hand deliver a check to each of them,

relating to their policies on Kenneth McDavid. Helen told the insurance company she'd prefer to meet the courier at her usual place of business, Izzy's Deli on Wilshire. Olga agreed to meet the company's messenger in the lobby of her bank later on the same day. That morning, Ed Webster took pains to dress for the occasion.

Charcoal gray suit, crisp white shirt with a light blue tie. It was a big day. The day he was finally going to meet Helen and Olga face to face. Riding along with him that day was LAPD detective Rosemary Sanchez. Sanchez was wired for sound and was carrying a hidden video camera.

As Ed pushed through the swinging glass doors at Izzy's, he saw Helen, primly positioned in her usual spot, table 22, corner booth, narrow window. Helen, somberly dressed for business, was also a study in gray that day. Dark gray cloak over a medium gray suit and a light gray sweater.

Gold-pended earrings dangled gently below her trademark bouffant. Her oversized glasses reflected shards of sunlight as she watched Ed weave through the breakfast crowd. Helen seemed to regard him with haughty disgust, as if he were an inconvenient errand boy, a necessary annoyance. I have no comments. I have no questions.

She never even asked for it. I mean, she just said, I mean, she clearly said that she was not going to answer questions. She was just there for a check.

And so she just identified her signatures on some documents, which is protocol, and produced some identification. I have some administrative details I have to ask you about. A letter for you to leave. Was she pleasant when you... No, that's not a word I would apply. Really? Yeah. I mean, you're a charming gentleman. You walked in, you said hello. Maybe she knew that I had been chasing them around for like four months already.

And they had been deliberately not wanting to speak with me, so I don't know what they thought. But pleasant was not a word that came immediately to mind. Then Ed pushed the envelope across the table. Inside was Mutual of New York's letter notifying Helen that they were rescinding the two McDavid policies, together worth a million bucks. Included was an $1,800 refund check for the premiums Helen had paid for the two policies.

there would be no New Year's payday for Mutual of New York. She just threw it and started yelling "unacceptable" and running around the diner. What do you think of that?

I didn't, stayed for a while hoping that maybe she'd have, she'd reconsider and maybe come back and sit down. But that wasn't going to happen. And that was the end of that meeting. So it doesn't really qualify as a real meeting.

As she was leaving, she raised her cell phone to her ear, as if she was about to make an urgent call. Just who she was calling, Ed didn't know, but he assumed it was Olga. Because when he and Detective Sanchez arrived at the bank where he was supposed to have met her, Olga was a no-show. We went to Olga's house. She didn't show up at the bank, predictably.

And again, there was really not much of a meeting. I mean, Olga seemed to be as hostile as Helen was. Olga was 100 times more. Had she been warned, do you suppose? Oh, I'm sure there was a conversation. In fact, I know there was a conversation between them. Otherwise, she would have clearly shown up at the bank. Olga, it's Ed Webster from Money Life Insurance Company. I'm sorry, can I get over the door, please?

I persuaded her to open the door, which was an accomplishment, and she opened it just a crack because I slid the letter in and told her she might be interested in it. Give me the letter. Here you are. Thank you.

We're going to wait while you read it. No, no, I don't want you to come in. I have my attorney. But then she opened the door again and threw the letter back out. Thank you. And she went absolutely ballistic. I mean, she was screaming and cursing and ranting and threatening to call the police and sue us. I mean, really, she went nuts on him. She went nuts. Cousin, call the police. Go ahead. Quick, slam me. You're going to break the door. I'm going to break the door.

Meanwhile, there's a police officer there with you. Correct. Watching all this? Yes. And then we heard her on the phone calling a friend of hers who came up from someplace in the building. Doug. Doug!

And she used him as sort of a battering ram and ran out of the apartment behind him like a guard for the New York Giants and ran, you know, bolted by us and into the staircase. There was another interview that wasn't going to happen. So that was it. I mean, that was the extent of my exposure to these women.

No. Helen and Olga would never lay eyes on Ed Webster again. But that was not the last time they'd be confronted with the investigation that Ed had started.

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As Democrats unite around Vice President Harris, they'll gather in Chicago to endorse their presidential ticket. A new era is here. It is go time. Stay with MSNBC for insights and analysis. The race is going to be close. Everybody should prepare themselves for that. Plus reporting on the ground from the convention hall. Extraordinary levels of enthusiasm from Democrats for the fight ahead. The Democratic National Convention. Special coverage this week on MSNBC.

By January 2006, the Detective Kilcoyne Granny Task Force seemed to be uncovering something new every week. Details, mostly. Details about the dead men. Details about the girls, Helen and Olga. And details about the insurance fraud plot the detectives believed was at the root of it all.

Ed Webster's rather contentious meetings with Helen and Olga just after New Year's 2006, well, that was like chum in the water for the white-collar sharks on the detectives' team. One of the things you do in pretty much any white-collar case is you subpoena everybody on the planet. Sam Mayrose, known as FBI Sam around the squad room, was one of those sharks. You're subpoenaing telephone records, you're subpoenaing bank records, all kinds of stuff.

So in one of Olga's checking accounts, I found a check written to a rubber stamp company in Hollywood. And so I called them and they said, oh, yeah, we know exactly who you're talking about. So I grabbed another agent off my squad and we drove over there. As the two agents jockeyed through traffic, they reviewed what they had learned so far. They knew that the two women had applied for multiple policies on Paul Vados and Kenneth McDavid.

They also knew that on most of those policies, the signatures had been remarkably consistent, as if literally rubber-stamped, perhaps. So, a rubber-stamped company that might have made stamps of victim signatures seemed like a good place to verify that hunch.

And also, maybe there were other names, other homeless men, rubber stamped and then rubbed out. I showed them a photo lineup that had Olga's picture in it, and they picked her out right away and said, oh, that's Olga Smith. We call her the Black Widow. And, you know, I said, Black Widow, why do you call her that? She says, well, because she's always coming in here ordering stamps for men.

Black Widow? The guys at the rubber stamp store didn't know the half of it. They'd been curious, sure. But when they asked Olga, they said, she told them the stamps were for official government business. She says, oh, well, I work for the county and I help these guys out and I take care of them, so I have to have their signatures for things.

It was a painstaking process, but the agents thumbed through roughly 10 years' worth of receipts, and sure enough, they found what they'd been looking for. The names of Paul Vaddis and Kenneth McDavid. Both had signature stamps. But that wasn't all. There were at least a dozen other names on the list of receipts credited to Olga Ruddersmith's alter ego, Olga Smith.

The agents, of course, had no idea if those other men were alive or dead. But at least they now knew who they should be looking for. We found some guys that we think that went back to Hungary. Nicholas Kuss, I believe, was one of them. Every day, it seemed, detectives learned something new about Helen and Olga. And every day it became clearer that the two women had been in cahoots for years.

Yeah, I'm not sure exactly when these two hooked up, but they may have kind of met each other at a gym somewhere there in L.A. and discovered they had some similar interests. They started hanging out at nice hotels, and they would find older men and flirt with them and, you know, steal their wallets, things like that.

Paul Pringle of the Los Angeles Times said the next step in Helen and Olga's evolution was to file a flurry of civil lawsuits against local businesses, tenants, and neighbors. As I remember, Olga was in a gym and chatting with a handyman, and she told him she made her living from suing people. One of the people she was suing at the time got wind of that and I think subpoenaed the handyman as a witness, and that caused Olga to drop the lawsuit.

In hindsight, investigators could clearly see the evolution of an insurance con. For them, the line from petty crimes to those lawsuits to the horrifying deaths of two vulnerable men couldn't have been straighter. And then, as the detectives and the LAPD task force were chasing down leads in the spring of 2006, they stumbled upon yet another name.

An old man who'd been killed by a car in 2000. That was the year after Paul Vados died. This new man's name? Fred Downey. Fred Downey was a lonely old man from Massachusetts, and he was in his mid-90s. How did a crusty old New Englander from Cape Cod get involved in all this?

Well, let's just say there was a woman involved. A young woman. A beautiful young woman named Golay, Keisha Golay, Helen's youngest daughter. She's working in New York City at the time, and she has occasion to go visit her sister up at the Cape, and they, well, she kind of steals old Fred's fancy. Fred was smitten.

He called her Bubbles. And Keisha, when she practically adopted Fred, called him Grandpa. He really hit it off with her, and she persuaded him to come with her to California and to move in, you know, the Golay home in Santa Monica. After a lifetime in New England, the prospect of spending his sunset years in California proved irresistible to Fred Downey.

Keisha told him her mother, Helen, had a vacant apartment in her building, just waiting for him to move in. He said, well, if I don't like it, I'll come back. That's Mildred Holman, Fred Downey's niece. Helen Golay was going to take good care of him. That's what he told me several times. But he didn't even know this woman named Helen Golay. I don't know whether he did or not. See, Helen Golay was Keisha's mother. I never met her. I never knew her at all. But, uh...

but he just trusted them so much. It was February 2000 when Fred Downey's California dream came true. In letters home to his niece, Fred said he was having the time of his life. Missing winter in New England? No way. This is another letter he wrote on February 16th, so he hadn't been there very long.

Well, I have finally arrived in California. Never dreamed I would wind up so far from New England. The temperature is in the 60s. Best apartment I was ever in. Huge oriental rugs. Helen and I occupy two of the four apartments. Ah, to be 96 and single in Santa Monica. Mm-hmm.

According to Fred, the Golay's even got him in a health kick. I walk about two or three miles each day. I only eat twice a day, no sweets. That means candy, ice cream, pies, cookies, it all. Naturally, with a regimen like that, Fred dropped a few pounds, getting his old beach body back.

At the doctor's the other day, with street clothes on, I weighed 144 pounds. That is down from 168. Guess I haven't been that low for a good many years. While the folks back in New England were bundled up, all winterized, Fred Downey was having a ball, basking in the California sun. He says in this letter, I sure like the weather out here. People are walking in their shirt sleeves.

But as spring turned to summer, Mildred said, Fred's letters took on a wistful tone. I guess I don't have any news. Things are very quiet. I've been out here almost five months now. It's okay, but it isn't good old Plymouth. Did Fred think California had been a mistake? Hard to say. In his letters home, Fred seemed to be saying he was spending a lot of time alone.

Helen was always busy with business. Keisha, busy with school. Busy, busy. No time for Fred. But even if he'd wanted to return to Cape Cod, there was really nothing to return to. He'd sold his seaside home in Cape Cod to Helen and Keisha for a buck. He'd given most of his savings to Keisha. He even changed his will so that Keisha would inherit everything.

Well, there's nothing illegal about any of that. It did leave Mildred and her family, his closest living relatives, high and dry. It was around Thanksgiving 2000 that Mildred got the very distressing news about her Uncle Fred. He'd been hit by a car and seriously injured. But what was odd was the way she found out about it.

It was very strange how I found out about the accident. I got a call from Mr. Davis, a local undertaker. Undertaker? Yes. And apparently he had a prepaid funeral, prepaid from way back. They said the only thing in his pocket that they found was Mr. Davis' address, the fact that he was the undertaker and his address. It was an accident.

Fred Downing had been crossing busy Ocean Park Boulevard when an unsuspecting motorist hit him. Didn't have a wallet in his pocket? Didn't have a wallet. Didn't have an ID of any other kind? That's what I was told. So the police or the hospital, someone contacted Mr. Davis, and he in turn looked around and found out

that I was the next kin. But Keisha didn't phone you? No, Keisha didn't phone me. What did she tell you when you finally did contact her? Well, she just said that he was not crossing, he did not cross the street in the crosswalk. So this woman hit him, and it was his fault because he wasn't in the crosswalk. How badly did she say he was hurt? She said he was hurt very badly, but she gave me hope. She'd say things like, "We think he'll be okay."

But Fred Downey wasn't okay. A few days after his 97th birthday, he died. And once again, the Golays failed to call his next of kin. I called to see how he was doing. And, oh, she said, I meant to call you before, but he died, I think, two, maybe three weeks before. A while before. Two or three weeks? Yeah. Has he ever phoned you? And she hadn't phoned me because she didn't want to upset me.

That's what she said. His next of kin. Yeah. And at that point, I was the only one. Those prepaid funeral expenses? You know, with inflation and all, Fred's prepaid funeral cost a bit more than his plan covered. So you'd be excused for thinking that the Golays pitched in. After all, Helen and Keisha now had every dime Fred Downey had to his name. You might even think the Golays would pay the cost of, say, shipping Fred's remains back to Cape Cod.

But no, you'd be wrong. So when I got the bill for, I don't know how many, probably around $800, perhaps, I don't remember. Wait a minute, they sent you the bill? Yes. Well, I sent it back to Mr. Davis. I said, send it to Keisha. She has the money. I thought for sure she would pay it, but she wouldn't. She sent it back, so I had to pay it. As for the Downey family keepsakes that Mildred hoped to pass along, they, too, were gone forever.

I really, really would have liked to have had my grandmother's jewelry and my great-grandmother's rocker. You know, I really would have liked to have had that, almost more than money, because I'm a great believer in family ties. In 2008, I went to the cemetery in Cape Cod where Fred Downey is buried, near his beloved wife, Meryl, who died a quarter century before him. With me was Mildred Holman.

Mildred was not pleased when I cleared away the dead leaves because there on either side of Fred Downey's grave were two gravestones, marking the spots where Fred hoped Helen and Keisha Golay would one day rest beside him. That is terrible. Look at that. Fred, Meryl, and Keisha. I never knew they were here. That is horrible. Keisha. Keisha.

Upsetting? Oh yes.

But as we said earlier, Fred Downey's name was not the only one detectives turned up while investigating Helen and Olga. Remember, detectives had found the names of roughly a dozen men at the rubber stamp company where Olga had ordered rubber stamps to duplicate their signatures. Were those men alive or dead? Were any of them targets? Well, remember Jimmy Covington, the homeless man who'd walked away from Olga after she'd pressed him to sign a lot of forms?

Jimmy's name was among those found at the rubber stamp company. And FBI Sam was desperate to find him. We couldn't find him. So we worked with the Social Security Administration and asked if they could stop his checks long enough for him to come in to talk to them. And they agreed. And so when he came into the Social Security office, myself and Rob Brockway from the California Department of Insurance were there.

Naturally, Jimmy was shocked when the investigators told him he may have been marked for murder by two elderly women. They said that they would take a policy out on me to try to murder me, but they didn't really let me know that they had already done anything else to anybody else.

Jimmy told the detectives he remembered Olga all right. She was the one with the paprika-accented English who kept pushing him for personal information. Though Jimmy had only been under Olga's eye a few days back in 2002, that was long enough. Investigators found that Helen and Olga had applied for at least one policy on Jimmy's life worth $800,000. There surely would have been more had Jimmy not left when he did.

After all, said Jimmy, Olga even woke him up at 3 in the morning once, demanding he fill out more forms. 3 in the morning, and didn't knock. All I heard was the door handle shake like that, and the key come in, and she cranked the door open, her eyes were sticking out, and she goes, did you remember any of that information? What are you doing right here? You got that paperwork filled out? He said, what are you doing? I said, I'm sleeping. And then she'd say, okay, I'll see you tomorrow. I'll bring you some more. And she slammed the door and leave. Jimmy Covington had moved on after that.

never knowing how much danger he'd been in. Mind you, so did Helen and Olga. They just moved on. Four months later, they had a new man in their lives. His name? Kenneth McDavid.

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As Democrats unite around Vice President Harris, they'll gather in Chicago to endorse their presidential ticket. A new era is here. It is go time. Stay with MSNBC for insights and analysis. The race is going to be close. Everybody should prepare themselves for that. Plus reporting on the ground from the convention hall. Extraordinary levels of enthusiasm from Democrats for the fight ahead. The Democratic National Convention. Special coverage this week on MSNBC.

The cascading chain of events that led Ed Webster to that rather frosty confrontation with Helen Golay at Izzy's Diner had begun in earnest a year earlier. It was around Christmas 2004. Investigators theorized that Kenneth McDavid sealed his fate.

In the spirit of the season, perhaps, Kenneth had invited a few friends to share the tiny apartment that Helen had been renting for him the past two years. But when the ladies discovered that Kenneth had house guests? Well, Detective Kilcoyne heard from people who were there. It wasn't pleasant. Well, there's a big blow-up one day with Helen and Olga, an armed security guard that turned out to be Olga's neighbors, to try to get them to behave properly.

According to one of the invited guests, the trouble started when Olga dropped by unexpectedly to check on Kenneth. Seeing the apartment full of interlopers, the man said, Olga cursed and ranted and demanded everyone but Kenneth leave. They actually hired a uniformed security guard who sat outside McDavid's door for a few days to keep other people away and basically hold him prisoner. But after that, they're evicted from that apartment.

So, when the calendar flipped from December to January 2005, Kenneth McDavid found himself back on the streets. Literally, off the leash, for the first time in two years.

He starts floating around Hollywood, and he was getting harder and harder to keep track of. Helen and Olga did their best to keep tabs. Helen footed the bill for a string of cheap motels along Hollywood Boulevard over on Sunset that Kenneth would flop in for a few days before moving on. They were losing track of him, and again, you know, they've got way too much money invested in this person now.

Oh, yes, about $65,000 worth in rent and food and insurance premiums. The detectives theorized it was then that Helen and Olga made a cold-blooded business decision. If Kenneth McDavid slipped away altogether, their investment would be down the drain. And even though some of the life insurance policies on Kenneth McDavid were still a few months shy of being two years old and so at risk of not paying off...

The girls decided they couldn't afford to wait any longer. Kenneth McDavid had to go. So they pulled the trigger a little early. Yes, and even if it meant that they may not be able to collect on all the policies. An interesting theory, perhaps, but, well, that's all it was. The fact was the detectives had no witnesses, no murder weapon, nothing that would put Helen or Olga anywhere near Kenneth McDavid on the night he died.

Might they have hired someone else to do the deed? Well, detectives wondered, but Kilcoyne didn't think so. One thing kept coming back to us is that they're just too greedy. There's no way that they would share this with anybody. If they could accomplish it themselves, they would do that rather than give somebody $500 to help them. But without proof that would stand up in court, the detectives could not make an arrest, at least not on murder charges.

And Detective Kilcoyne was nervous about letting the ladies roam around L.A. free. Remember that surveillance team that had been shadowing Olga? In the spring of 2006, they actually saw her meet several times with an elderly man. From a distance, it looked as if she might be working up a new victim, circling like a hawk, preparing to dive in a field mouse.

There's an elderly man that she meets with, that she takes to the bank, that she... And every time she meets with the guy, he's gonna come out of his apartment and walk, like, over a block or two to meet with her.

And we, surveillance people, took pictures of her pointing out on the deck of his trunk lid of her car. And she's pointing, he's signing forms and this and that. We can imagine that she's got him signing insurance policies. Well, how old did this man appear to be? Oh, this guy was probably in his 70s or 80s. The man's name, detectives learned, was Joseph Gabor.

Like Olga and Paul Vados before him, Gabor was a Hungarian immigrant. After watching Olga's courtship of Joseph Gabor and seeing him sign some documents, the detectives knew they had to move in and move quick. The old man's life expectancy likely had a rigid number of years attached to it now, a number more precise than any actuarial chart. What are we doing? How do we stop it? We can't just stand by and have surveillance on these women and watch them kill another man.

It was time for action. The detectives hadn't gathered enough evidence to arrest Helen and Olga on murder charges, at least not yet. But insurance fraud? Mail fraud? The feds on the task force felt that was a slam dunk. These are federal charges and these things, they say it's the United States of America against you. That's pretty impressive.

And so after nine months of keeping a close eye on Helen and Olga, the Granny Task Force was ready to make its move.

On the morning of May 18th, 2006, dozens of lawmen gathered outside Helen and Olga's apartments, geared up as though they were preparing to storm the Bastille. Well, Helen's house was like a fortress, and it has a big block wall all the way around the compound. So the only way you get in there is with a key or you scale the wall. So the officers...

scaled the wall, went in. Okay, let's go ahead and sit in the car. Why don't you do this to me? This is like you're killing me. Look at this. In simultaneous raids, local, state, and federal lawmen converged on the apartments of the two old ladies.

as if they'd finally cornered Bonnie and Clyde. Oh, God! You dragged somebody naked from the bed like this? You want to take custody of her? This was shock and awe. Olga was marched out of her apartment barefoot in a flimsy nightgown.

Even then, she struggled with officers who had her handcuffed behind the back. I have arthritis. Don't be so rough. I had surgery. I had surgery. I get very sick. I know. My arm. Can you take off this officer's earring? I have a nose that is so hard. Wait. Wait.

Helen, in silk pajamas, stood gate-mouthed outside her apartment as the FBI's Sam Mayrose made clear this was serious business. Ms. Goulet? My name is Sam Mayrose. I'm with the FBI. You're under arrest for mail fraud. Mail fraud? Yes.

I haven't done any mail fraud. What are you talking about? Insurance. She looks at me and she says, who could do this to me? Who could do this? I don't understand how anyone could do this to me. I'm like, what do you mean? You did it to yourself. So you're under arrest. I know, but let's just go with the program. Turn around. Turn around. 75-year-old woman that's not going to come out of my way. That's right. So we're not going to have any problems then. It was crazy. I mean, it was just like...

It's kind of like what you expect from this whole scheme. I didn't do anything wrong. You killed two guys. You took a bunch of money that you stole from the insurance companies. Of course you did something wrong. But that's how she gets along. Video from the scene shows Helen being hustled into a police cruiser, flustered but keenly aware of the camera. This is awful. Yeah, and I won't look very pretty on your camera either. Okay.

Once the two women had been placed in squad cars, each was shown a copy of their arrest warrant. This is a bunch of lies. I know you don't care. Oh my, that's a lie. This is an assumption. Let's just keep it. Any time, my God. But how can they accuse somebody without any proof?

Proof? That seemed to be piling up even as she spoke. The federal agents had come armed with search warrants. So, even as the ladies were being whisked away to the Federal Processing Center, the investigators were gathering evidence. Helen, it turned out, kept impeccable records, archived in boxes clearly labeled "insurance policies, leasing agreements, rent receipts."

Olga, on the other hand, took a more eclectic approach to business matters. In her apartment, investigators found scribblings in calendars and random notes to herself. Some of those notes looked to be itemized listings of Helen's out-of-pocket expenses, expenses relating to both Kenneth McDavid and Jimmy Covington.

She had made all kinds of notes about how much they had to pay for insurance premiums each month and rental spaces, how much they were paying in utilities. It was a treasure trove of documents for the fraud. Of particular interest to the homicide detectives was the taser that Olga kept in her dresser drawer and the prescription drugs Helen had on hand.

Drugs that matched the chemical compounds listed in Kenneth McDavid's toxicology report. But on the day Helen and Olga were arrested, FBI Sam said one item particularly in Helen's apartment grabbed his attention.

just as surely as if it had spoken to him. The thing that immediately hit us, she had a, if I remember right, there was like a lazy boy chair right near the front door. And there was a side table there and sitting on the side table was a book, A Sociopath That Lives Next Door.

And we all looked at and we just started laughing. I mean, really? I think the sociopath lives right here. But anyway, of course, I'm not a doctor. You didn't need a diploma on the wall to figure out there was something off the wall about Helen and Olga. No, all you had to do was get them alone together and listen. Oh, my God.

Helen, that's your fault. You cannot make that many insurances. It's on your name only. Three, four, three different extra insurances. You know what? I want to ask for a different location if you're going to talk. I don't want to talk. Don't talk to me. But it's three insurances on your name. I don't want to talk to you. You have to because you did all these insurances extra. That's what raised the suspicion. You can't do that stupidly.