Transcribe your podcast
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This is crime house.

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People will do just about anything for love, even if it means ignoring huge red flags waving right in their faces. This can be especially true for lonely older folks in need of companionship. Maybe theyve lost a spouse, someone who was their lifelong partner, and now they cant bear the idea of facing the future alone. That loneliness can make people super vulnerable. And if theyre not careful, they can get taken advantage of by someone like Melissa Ann Sheppard.

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On the surface, Melissa seemed like a pleasant, charming woman. But underneath the smiles and the maternal vibes, she had a dark side, a very dark side. People who knew her couldnt put their finger on it at first. But when one partner after another wound up either dying or dead, there seemed to be only one common denominator. Well, two, Melissa and a trail of emptied bank accounts.

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As the saying goes, those who dont understand history are doomed to repeat it. Thats especially true when it comes to money. If you want to make the right decisions when it comes to managing your assets, you need to know what mistakes to avoid and how to spot a trap. This is money, a crime house original im your host, Nicole Lapin. Every Thursday, ill be telling the story of a famous financial crime and giving you advice on how to avoid becoming a victim yourself.

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This episode is about Melissa Ann shepherd, better known as the Internet Black Widow. Its an interesting one, because, unlike some of our other stories, were not dealing in sums in the billions here, or even millions. Melissa Ann shepherd was dealing in much smaller amounts than that. But she was plenty dangerous. Starting in the late 1980s, Melissa preyed on older, lonely men.

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She used her charm to drain their bank accounts and, in some cases, end their lives. Today, I'll tell you about how Melissa spun a web around her targets, luring them into a false sense of security. And when they were at their most vulnerable, she attacked.

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On the east coast of Canada, tucked away off the shores of Nova Scotia and New Brunswick, is a small province called Prince Edward island. Think lighthouses overlooking red sand beaches, quaint cottages and farmlands as far as the eye can see. So you could imagine how it could feel a little lonely there. How youd want companionship, someone to snuggle up with on cold winter nights and to kick back with a refreshing drink on warm summer days. Melissa Ann shepherd had that in 1971.

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She was 36 years old and had been married to her husband, Russell, for about 16 years. But then Russell got diagnosed with a rare form of cancer called Hodgkins lymphoma. He was too sick to work, and the bills started adding up. Thats when Melissa reportedly began writing fraudulent checks just to get by. But she wasnt exactly a criminal mastermind, and eventually Melissa got caught.

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She was convicted on 30 counts of fraud, forgery, and impersonation and ended up serving five years behind bars. Through it all, Russell, whose cancer seemed to have gone into remission by this point, stood by her. By the mid eighties, Melissa was in her fifties and was finished serving her time. Looking for a fresh start, she and Russell moved to a new town on Prince Edward island in Canada. Unfortunately, Russells loyalty and their home didnt seem to be enough for Melissa.

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Within a few years, her eyes started wandering, and around 1989, they landed on 42 year old Gordon Stewart. Gordon was a widower whose wife had died of cancer three years earlier. He may have still been grieving the loss, but his loneliness was all consuming and he longed for companionship. That was when Melissa walked into his life. She was charismatic and charming, and Gordon fell hard for her.

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Hard. It's unclear whether Melissa genuinely fell for Gordon, too, or if she saw him as a mark from the beginning. You see, he was a former army man with a pension and cad50,000 in the bank, and that was back in 1989. Money so that 50K would be worth somewhere in the ballpark of 90,000 to 120. So not a ton of money in the grand scheme of things.

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Whether it was for the money or Gordon himself, Melissa had hearts in her eyes. The two of them whisked away to Las Vegas and got married. Despite the fact that Melissa was still married to her first husband, Russell. It's not clear if Gordon knew that or what the situation was exactly. But after they got back from their honeymoon, Melissa did eventually divorce Russell.

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And once the marriage to Gordon became official, she had full access to his money. Of course, there was no prenup here. But what would have happened if Gordon had insisted on one? Contrary to popular belief, having a prenup doesn't mean you think your marriage is going to fail if it makes you feel better. Everyone has a prenup in one way or another.

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It's just a matter of whether or not you're okay with the government's standardized divorce agreement or if you want to personalize it for you and your partner. When you have a prenup, it protects the assets that you bring to the marriage. So if you're like Gordon and you have your own money saved, that can remain your property as long as it remains in a separate account. It's a safety net, just in case. And if you have a lot of assets, it's a good way to make sure your partner isn't just marrying you for the money.

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And if Gordon had asked for one, what happened next may have been avoided. But as it was, Melissa now had full administrative access to Gordon's bank accounts, and she immediately started to siphon off the money. Gordon didn't realize what was happening, probably because he was dealing with health issues at the time. You see, he was passing out constantly. Gordon chalked it up to his struggles with alcohol abuse and being on the wrong side of 40.

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But his family worried that something more nefarious was going on. Whether they suspected Melissa had some part to play in the fainting or not, they certainly thought she was taking advantage of his sudden illness. But Gordon waved off their concerns. He never suspected Melissa was responsible for a second. After two years together, Melissa and Gordon decided to get a new place in a different part of Prince Edward island, just like she did with her first husband, Russell.

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Melissa said the move would be a way to give them a fresh start. But only a week into the new living arrangements, things took a turn for the worse. One night, Melissa showed up at the police station in a total panic. She said that Gordon had held her at knife point and forced her into their car. She claimed he had driven them out to a remote logging road, where he raped her.

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When Gordon got out to relieve himself, Melissa jumped into the driver's seat and threw the car in reverse, trying to escape. That's when she hit something. According to her, she thought it was a log at first, so she reversed again. But then she realized it wasn't a log. It was Gordon.

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In her rush to get away, she had run over him twice and killed him. Except Melissa's story didn't totally add up. For one, tests showed that at the time of Gordon's death, he had a near lethal dose of a sedative called benzodiazepine in his system and a ton of alcohol. The police found it hard to believe that a man in that state could have forced himself on Melissa. The amount of narcotics in Gordons system would have made it hard for him to even walk.

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It wasnt long before the police suspected this wasnt an accident at all. They were pretty sure Melissa had purposefully run over her husband, and she had done it for his money. After Gordons death, his armed forces pension became hers, along with all of the money left in his bank account. Melissa went on trial for his murder. But ultimately, the jury wasn't convinced and only found her guilty of the lesser charge of manslaughter.

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The judge sentenced her to six years in prison, although she only served two.

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In 1994, Melissa, who was now almost 60, was a free woman once again. Upon her release, she turned into a spokesperson for battered women. She actually went all over Canada giving speeches about defending herself as the victim of an abuser, and she became a familiar face for the cause. After a few years, Melissa pulled back from her work as an activist and left Canada entirely to relocate to Florida. Maybe she was just ready for the warmer weather and needed another fresh start.

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Or maybe she landed there because it was a popular retirement destination full of wealthy, lonely men. And as fate would have it, that's where she met husband number three.

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It was now 2001, and 66 year old Melissa Ann Sheppard sat in the pews of a Florida church. That's where she first caught sight of Robert Friedrich. Robert was an engineer and a retired widower and a devout Christian in his eighties. Melissa immediately locked onto him. After the service, she wrote him a letter saying that God himself had told her they belonged together.

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Apparently that did it for Robert. They got engaged just three days after they met, and a month later they were married. They soon set off on a five month honeymoon that culminated in a luxury cruise around the Caribbean, all paid for with Roberts life savings of approximately $250,000. Naturally, Roberts family was skeptical of this new woman in his life, and the sudden marriage and expensive honeymoon werent the only shady things going on. All of a sudden, Robert was falling down all of the time and ending up in the hospital.

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That just didn't sound like him, especially because whenever he visited his kids, he was the same old Robert, a robust, healthy guy in his eighties who still had his wits about him. But whenever they talked on the phone when he was at home with Melissa, Robert slurred his words and sounded off. Roberts family knew they had to do something before it was too late. So one of Roberts sons called the elder abuse agency in Florida and reported his suspicions. The agency performed a welfare check and apparently didnt suspect any foul play, although they did recommend that Robert have 24/7 nursing care.

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But Melissa straight up refused to let that happen. She also threatened to sue the agency that had made the recommendation. So they backed off and they didnt follow up. All of this made Roberts family even more convinced Melissa was responsible for making him sick. But before they could figure out how she was doing that, one of Robert's sons received a voicemail.

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It was from Melissa. She said that he and his two brothers were being taken out of their father's will, and she wasn't nice about it either. She ended the message saying, quote, you guys are getting nothing, a big fat zero. So try that on for size and have a nice day. This was a huge shock to the kids.

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They wanted to fight for it, but they didn't know how. Which raises the question, if you are wrongfully cut out of a will like this, what can you do? Now, bear in mind, I am not a lawyer, so none of this is hard and fast legal advice, but it's important to know that if someone changes their will under undue influence, duress, or due to fraud, that wrongfully updated will can and should be voided by the courts. However, you will need to have evidence to prove your case, which is why you should always put things in writing, even if you don't think anything fishy is going on. It never hurts to have your bases covered.

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But in the event that you do think something is off, you should speak with a probate attorney and challenge the will as soon as possible. The longer you wait, the harder it will be. As time goes on, witnesses become less reliable and it can be harder to find the evidence you need. It's also easier to challenge a contested will before the proceeds of the estate are distributed. Once the will is executed and the assets distributed, it can be extremely hard to collect what you're owed.

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Unfortunately for Robert's sons, they didn't contest the new will. Melissa had urged Robert to sign, and it wasn't long before she got what she wanted. Less than 18 months after Melissa and Robert got married, he died from cardiac arrest. But Roberts sons were not buying it. They filed a criminal complaint accusing Melissa of overdosing their fathers prescription medication.

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But they couldnt sufficiently prove it, and she was never charged. Once again, Melissa was down a husband and flush with cash. As Robert's wife and next of kin, she had control over all his finances and was presumably the sole beneficiary of his will. At this point, before anyone could try and stop her, she sold his house, collected some insurance money, and ended up pocketing about $100,000. When all was said and done, then Melissa went back to Prince Edward island in Canada.

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With Roberts money in hand, she now collected around a quarter of a million dollars from her deceased partners, not to mention all of the money she'd persuaded them to spend on her while they were together. But it still wasn't enough to find her next victim. Now 69 year old Melissa turned to an entirely new dating pool, the Internet. And at the end of 2004, for just a little over two years after Robert died, Melissa found the online dating profile of 73 year old Alex Strategos. She started messaging him and before long, they decided to meet in person.

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Alex lived back in Florida, the very place Melissa had just left behind. But she saw something in him that made the travel worth it. So she made the long drive south and met Alex for a dinner date. When he asked her where she was staying, she admitted that she didn't have anywhere picked out yet. In that case, he said, why didn't she stay the night with him?

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Melissa didn't need to be asked twice. They went back to his place, and in the middle of the night, Alex got up to use the bathroom. When he did, he felt dizzy. He stumbled. Then he passed out.

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Melissa called 911 for help, and the ambulance quickly arrived to whisk Alex to a local hospital. By the time he was discharged, Melissa had already moved into his house to care for him. This was even faster than her last two relationships. Alexs son, Dean, certainly thought it was way too much too soon, but he also knew his dad couldnt live by himself. Still, Alex was a grown man who could make his own choices, and he seemed to genuinely like Melissa.

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Dean told himself that maybe it would all be fine. Unfortunately, Alex kept falling and passing out of he ended up back in the hospital eight times over the next two months. Eventually, it got so bad that he became wheelchair bound and ended up in a nursing home, possibly at Melissa's suggestion. Now Dean was even more powerless to help his dad because Melissa had convinced Alex to give her power of attorney. That meant that she was in complete control of his assets.

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She could sell his condo, shut down his bank accounts, change his will, anything. Melissa swore that she was only doing it to help Alex out while he recuperated. But Dean saw right through her. He told his friends what was going on, and they helped him get in touch with a detective. When the detective started looking into things, he realized that Melissa had drained about $18,000 from Alex's bank accounts.

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It was nearly everything he had. The detective also dug into Melissa's background and found that she had more than 30 fraud convictions, plus various aliases. And she had multiple husbands who died under mysterious circumstances at the same time. Dean went to the hospital and asked to see his dad's medical records. Surprise, surprise.

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Alex had tested positive for tranquilizers, benzodiazepine, to be exact, the same drug found in Melissa's second husband after his death. All of that painted a not so savory picture. The detective brought Melissa in for questioning while other officers searched Alex's condo for evidence of foul play. Sure enough, they found bags of different pills, along with messages on Melissa's computer to several other men. She already had new dates lined up, presumably to find her next victim.

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Thankfully, the authorities put those plans on hold. They figured out that Melissa had been drugging Alex with the ice cream she gave him every night. Surely the next part of the plan was to sell all of his assets and cash in. But she never got the chance. Melissa pled guilty to seven fraud charges, and a judge sentenced her to five years behind bars.

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She was released a bit early, getting out after only four years, when she was then 74. Before she could trap any more hapless Florida men in her web, Melissa was deported back to Canada. But with the power of the Internet, Melissa could be on the prowl from anywhere. No matter where she lived, there was an endless sea of lonely older gentlemen who might fall prey to her ways.

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Melissa Ann Sheppard got released early from prison and deported back to Canada three years later. In 2012, she was living in a retirement community in the province of Nova Scotia. She was leading a quiet existence until one day when a new tenant moved in four doors down. His name was Fred Weeks. He was 75 years old, and hed just lost his wife the year before.

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Melissa was nothing if not a good neighbor. She went over to Freds place to say hello. She said she had heard he was lonely and that she was lonely, too. And wouldnt you know it, they hit it off. It wasnt long before wedding bells were ringing again.

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Melissa and Fred had a civil union ceremony in his living room. And for those in attendance, the two appeared genuinely happy. Of course, Fred had no idea about Melissas past. She just seemed like the nice woman from down the street. After the ceremony, the two love birth headed off on a ferry ride to Newfoundland for their honeymoon.

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And then Fred started feeling under the weather. He had trouble driving, getting a little hazy and forgetful. It got so bad, he couldn't even remember how to start the car. At one point, things got worse from there. He couldn't manage to put on his own shoes, and eventually he needed the assistance.

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A wheelchair. Things came to a head when they returned to Nova Scotia and checked in at a bed and breakfast. They retreated to their room, where Fred vomited all night long. The B B's owner got worried, so she went to their room to see if there was something she could do to help. Melissa answered the door and said they both had been sick all night long, but Fred was the only one who looked ill.

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The next day, Fred fell out of bed and hit the floor. So hard he needed to go to the hospital. But when the B and B's owner offered to call an ambulance, Melissa waved her off. She wanted to finish eating her breakfast first. Once she was done, Melissa agreed to take Fred to the hospital.

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And even when she did, she lied about his health conditions and told doctors that she was his only family, even though Fred had six adult children. The staff took Melissa at her word and tried to figure out what was wrong with Fred. At some point, they ran a toxicology report and yep, you guessed it, his body had near lethal levels of benzodiazepine. Once again, Melissa had been spiking Freds food, although this time it had been coffee instead of ice cream. The hospital staff immediately called the police, and it didn't take long for the authorities to discover Melissa's rap sheet.

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Given her long and sordid history, they quickly charged her with attempted murder. But even with Melissa's clear pattern of behavior and the presence of tranquilizers in Fred's bloodstream, there still wasn't enough evidence for the murder charge to stick. It was lessened to an act of distributing a noxious substance. Melissa pled guilty. At her sentencing, the judge told the court that anyone in contact with Melissa should be careful, that her history showed she would in all likelihood try something like this again.

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Still, the judge only sentenced Melissa to three years, yet another light punishment, considering the maximum sentence could have been up to 14 years. This time, at least, she did actually serve the whole sentence. And when she was released in 2016 at the age of 80, there was some attempt to make sure she couldnt hurt anyone else. There was a whole host of conditions for her release. She had to tell authorities about any future romantic encounters so those men could be warned of her history.

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She had to keep the police informed about any changes to her appearance or living situation, and she was banned from using the Internet point blank. Authorities also issued a warning to the community, cautioning that a high risk offender was being released back into the community. But would that actually help?

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As with any crime and one of the reasons im doing this show awareness is the first step to avoid becoming a victim of a financial crime. And this only becomes more important as Internet scams become more sophisticated. Spam filters are pretty good at catching the obvious ones, but what about when you get an email that looks like it's from your bank asking you to verify a purchase? You don't think too much about it. You just click the link, you pop in some bank account information or maybe your Social Security number, and you're good to go.

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But in reality, you've just become the victim of a phishing scam spelled with a ph. In order to avoid these types of the Federal Trade Commission suggests using multi factor authentication for your accounts, using security software on your computer, and always keeping your cell phones operating system up to date. Also, know that legitimate companies will never email you a link asking you to update payment methods immediately. You should always navigate to the actual company's website or app and sign in there. Generally, online scammers are casting wide nets, but there are still people out there like Melissa who take a more tailored approach.

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And unfortunately, about a month after her release, Melissa was right back to her old ways. She went to a public library where she sat down at a computer, logged in and booted up the Internet in direct violation of her release terms. Given everything we know about Melissa and her patterns, she was almost certainly using the Internet to look for a new man. Thankfully, Melissa got caught before she could sink her teeth into anyone else. She was immediately re arrested and given a court date for the following month.

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But for unknown reasons, the latest round of charges against Melissa got dropped. Her two living victims disagreed with the decision. Both Alex Strategos and Fred Weeks thought she should be back in prison, safely away from potential murder victims. But then theres the question, was she actually trying to kill anyone? Melissa's former lawyer doesn't think so.

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He said that his client was undoubtedly guilty of drugging her partners, but he didn't think she actually had the intention of killing them. In his opinion, her goal was to influence them in order to have them change their wills or insurance. That didn't make her any less dangerous. It's simply her motivation that's in question. Melissa, who at the time of this recording is 89 years old and still bound by her release terms, admits to killing husband number two, Gordon Stewart, but she maintains it was self defense.

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She also maintains that husband number three, Robert Friedrich, died from cardiac arrest and nothing more. She doesnt have explanations for the drugging of her boyfriend, Alex strategos either.

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So what can we take away from her story? For me, it shows how easy it is to be taken advantage of, especially for the elderly. For those of us who have a loved one who's getting older, it's our job to make sure they're not falling victim to scammers like Melissa Ann shepherd. Obviously that's easier said than done. We can't be by their twenty four seven and they are grown adults who can make their own decisions.

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But there are steps you can take to help. If you think an older person you know is being taken advantage of financially? The US Consumer Financial Protection Bureau recommends calling adult protective services or AP's, although it might go by a different name depending on where you live. You can also report it straight to your local police or district attorney. If you do make a report, make sure you have as much documentation as possible.

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It's hard to prove a financial crime without a paper trail, so you need to be able to come up with the receipts literally. Otherwise, predators like Melissa Ann shepherd are waiting to strike and they can take down anyone who isn't being careful.

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Thank you so much for listening. I'm your host, Nicole Lapin. Come back next time as I take you through another wild story and offer you some advice along the way. Money Crimes is a crime house original join me every Thursday for a new episode here at Crime House. We want to thank each and every one of you for your support.

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If you like what you heard today, reach out on social media, Rimehouse on Instagram, rimehousestudios on TikTok, rimehousemedia on X. Don't forget to rate and review and follow money crimes wherever you get your favorite podcasts. Your feedback truly makes all the difference. Money Crimes is hosted by me, Nicole Lapin, and is a crime house original powered by Pave Studios. It is executive produced by Max Cutler.

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This episode of Money Crimes was produced and directed by Ron Shapiro, written by Alex Burns, edited by Alex Benedon, back checked by Sheila Patterson, and included production assistance from Sarah Carroll.