Pod Insights Scamfluencers Conrad Black: The Fleet Street Fleece | 154 About this episode Conrad Black turned ownership of a single Canadian newspaper into a global media empire, and he used his wealth and status to cozy up to conservative superstars like Magaret Thatcher and Henry Kissinger. For years, he and his business partner lived large, looted company coffers to buy gulf stream jets, fund pet charity projects, and of course, throw lavish parties with famous people. But when a savvy investor reveals his self-dealing, Conrad will face the fight of his life to preserve his status and stay in the black.
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Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Sarah Hagi? Audible subscribers can listen to all our episodes of Scamfluencers ad-free right now. Join Audible today by downloading the Audible app.
0:13 Scaachi Koul? Sarah, what do you think when I say the words Conrad Black?
0:16 Sarah Hagi? Oh, my god, the boogeyman. I mean, I feel like he just kind of hovered over our lives as Canadians. I know that he was the publisher or the owner of National Post, which is a newspaper, some might say.
0:30 Scaachi Koul? Yeah, I did say a newspaper.
0:31 Sarah Hagi? But, yeah, he was always in the news for going to court, fraud. He's just like one of those people that you hear about when you're a kid and you're like, oh, yeah, that's adult stuff. And then you become an adult and you're like, oh, bad man.
0:44 Scaachi Koul? Yeah, his specter loomed very large. He was like the Babadook. I was afraid of him all the time for some reason.
0:51 Sarah Hagi? Definitely scary guy.
0:53 Scaachi Koul? Well, you know, I love when a scam brings us back home. And this week, we're heading back to Canada to hear about one of our very own fraudulent businessmen. And Sarah, if you were hoping today's scammer would inexplicably be connected to every living evil person from the last three decades, I have a treat for you.
1:15 Scaachi Koul? It's May 2005 and Conrad Black is sneaking through the back door of his company's headquarters, a grand historic building in central Toronto with huge Greek columns lining the entry. Conrad is in his early 60s. He's tall and broad with bushy eyebrows and neatly combed gray hair. He looks like a classic movie villain, and the fact that he's a multimillionaire only makes this vibe stronger. Conrad is the head of Hollinger, Inc., an international media empire, and he's a caricature of wealth. He travels everywhere in a 1958 Rolls Royce limo, and he often attends black tie events. But tonight, he doesn't want anyone to notice him, so he's wearing an inconspicuous blue suit and using a matching dark blue Cadillac as his getaway car.
1:59 Scaachi Koul? Despite his nice life, Conrad is not in the best place right now. For the last two years, he's been fighting allegations that he's been stealing tens of millions of dollars from Hollinger to keep up his luxe lifestyle. Now, he's under criminal investigation in the US and in Canada. He denies the allegations, but he's quickly heading towards a legal dispute that could ruin his entire life. And Conrad's on thin ice with more than just his investors. His best friend and longtime business partner, David Rattler, hasn't spoken to him in months. But worst of all, and to Conrad, this really is the worst part, his famous friends have stopped returning his messages. No one is coming to save him from this mess. So he has to save himself by raiding his own office and destroying all the evidence.
2:44 Sarah Hagi? You know, when a story starts with destroying evidence, you can only wonder where it will go from there.
2:53 Scaachi Koul? It's a really promising start. Well, Conrad has returned tonight to remove boxes of documents from Hollinger's HQ. He's not totally alone. With him is his devoted assistant of 11 years and his chauffeur. Because he's under investigation, he isn't allowed to take anything from his office without the approval of a court-appointed inspector. And Conrad knows that the boxes he's targeting would never be approved because they contain papers that would implicate him in decades of self-dealing. Conrad and his paid accomplices rush to pile the boxes in his Cadillac before anyone spots them. But that's when Conrad notices a security camera staring down at him, one that he hasn't installed himself. Someone's watching him cart off all the evidence. But it's too late to look back now,
3:37 Scaachi Koul? so after grabbing about a dozen of the most important boxes, the gang of thieves drive off into the night. Their plan is very simple: dispose of the evidence and save Conrad from getting caught up in an international financial scandal. Conrad's used to getting his way. For years, his rule-breaking brought him wealth and gave him access to influential circles, plus an extensive collection of Birkins for his wife. It's no surprise he feels untouchable, even in the face of possible jail time. But his smoke-and-mirrors lifestyle is about to catch up with him, and he's gonna have to pay for it in more ways than one.
4:21 Scaachi Koul? From Wondery, I'm Sachi Cole. And I'm Sarah Haggie. And this is Scamfluencers.
4:35 Scaachi Koul? Lord Conrad Black is an international media mogul who spearheaded one of the most prominent conservative media conglomerates in the world. It was a bastion of right-wing news coverage that launched Conrad into a social circle filled with billionaires, intellectuals, and even monarchs. Conrad loved holding court at star-studded events and lavishing his wife and family with opulent gifts. And when his bougie lifestyle soars as his company's bottom line sinks, investors and regulators start to wonder how he's keeping himself in the black. This is Conrad Black, the Fleet Street Fleece.
5:13 Scaachi Koul? It's 1957 in Toronto, and 13-year-old Conrad Black is breaking the rules. As usual. He's brazenly walking off school grounds to his chauffeured limousine with a group of his friends. Conrad's skinny, with red hair and a dorky disposition. He's a student at Upper Canada College, a prestigious private school for boys. Students aren't allowed off-campus during school hours, but Conrad loves sneaking off to his waiting limousine to read comic books at lunchtime. Surrounded by a group of peers he's hand-selected. Conrad's used to being treated like a prince, and that's because he kind of is one. He lives in a mansion in one of Toronto's most exclusive districts, and he's the son of George Black, the president of Canadian Breweries, the largest beer producer in North America.
5:57 Scaachi Koul? While he's not handsome or athletic like his dad, they do connect over a love of books, chess, and wordplay. Conrad also shares his dad's love of important men from history, like Napoleon and newspaper magnate William Randolph Hearst.
6:11 Sarah Hagi? Can you read what Conrad later wrote about Hearst?
6:13 Scaachi Koul? Yes, he wrote, "All his life, Hearst had a conviction, often outrageous, but sometimes magnificent, that the rules that applied to others didn't apply to him."
6:24 Sarah Hagi? Yeah, you know, people love saying this. They do it to validate why they're special. Like, this person was special because he didn't follow the rules, and I'm gonna be special because I won't follow the rules.
6:35 Scaachi Koul? Yeah, they're making it sound like it's virtuous to just do whatever you want. And Conrad doesn't feel like he needs to play by the rules either. At the age of 14, Conrad breaks into his school's office. He steals a bunch of final exams and then sells them to his fellow students. He charges them on a sliding scale, depending on how much their parents are worth. When Conrad gets busted, he's immediately expelled. His father claims his son is just being entrepreneurial, but the expulsion sticks. The peers Conrad sold papers to are all forced to sit their exams again, which means he's now persona non grata socially. His ex-friends make it official by burning an effigy of him on the front lawn of his house.
7:14 Sarah Hagi? Wow, that is very, very intense. And, you know, it's because there was no cyberbullying back then.
7:21 Scaachi Koul? Yeah, this was really the only way for them to do it.
7:23 Sarah Hagi? Yeah.
7:24 Scaachi Koul? Well, then, five months later, the black family is thrown a curveball. Conrad's dad has a fallout with his business partner over the direction of their company. He ends up taking an early retirement to avoid being fired. Though the family is okay financially, Conrad's dad never recovers. He falls into a depression and drinks every day, a lot. Conrad's dad was a successful businessman who played by the rules, and he had it all taken away. Seeing his father crumble teaches Conrad that work and success are everything, and that people will always be waiting to take it from you. He becomes obsessed with making something of himself. And if he has to bend some rules to get to the top, that's just fine with him.
8:08 Scaachi Koul? A decade after Conrad gets expelled, David Radler sits in his father's restaurant in Montreal. David is 27 years old, tall, skinny, and likely much younger than the majority of the patrons. The restaurant is called "O Lutanki Buff", which means "The Elf That Gorges". It's filled with wooden chairs and round tables covered in checkered tablecloths, and it has an old-fashioned, homey feel about it. The restaurant's also famously home to a group of tiny piglets, which guests can bottle-feed. We have a picture of one typical night at this restaurant. Sarah, can you describe it?
8:42 Sarah Hagi? Yeah, it's an average day in Montreal. It's a bunch of people sitting at a table, and they're eating dinner, and this woman is bottle-feeding a piglet. And, listen, a piglet is very cute.
8:55 Scaachi Koul? I would do this.
8:56 Sarah Hagi? But do I want animals around my food in any world?
9:01 Scaachi Koul? Yeah, you're right.
9:02 Sarah Hagi? Absolutely not.
9:05 Scaachi Koul? Well, you have to admit it's a cute piggy.
9:07 Sarah Hagi? It's a cute pig, of course.
9:08 Scaachi Koul? Yeah. Well, David is an entrepreneur, and tonight, he's dining with a law school student, Conrad Black. They run in the same conservative circles, and David was impressed with Conrad's knowledge and ambition. They're two young men determined to fill the shoes of their successful businessman fathers, and they bond over their shared childhood hobby: investing in the stock market. You know, normal stuff. About a year later, David joins Conrad in a new venture: buying a local newspaper, The Sherbrooke Record. It costs them $20,000 Canadian, or over $100,000 US in today's money. But the newspaper is struggling. And as the finance guy, the responsibility of fixing this falls mostly to David.
9:52 Scaachi Koul? Luckily, he's just the man for the job. He revels in pinching pennies, although his tactics are questionable at best. He starts by cutting the staff at The Sherbrooke in half to reduce overhead costs. And rather than have set salaries, David and Conrad sit down at the end of every week and decide what they think each reporter deserves to be paid. He also waits to pay the paper suppliers until their demands get nearly violent. David's a ruthless careerist with a photographic memory for numbers. He was practically built to be the money man. And within three months, The Sherbrooke is making a profit.
10:27 Sarah Hagi? You know, I think the fact that this is how they view journalists, it's like, hmm, how much do they get paid? Let's see what they did this week, and we'll figure it out from there. To me, it's just like, OK, these people don't care about news. They don't care about journalism or anything. It's just kind of a way to be powerful and, as we know, start an empire.
10:45 Scaachi Koul? It's so evil. Over the next few years, David and Conrad go on a buying spree, quickly growing their media company. They continue to use this slash and don't pay strategy, gaining profits and plenty of enemies in the news world. In the early 70s, David moves to British Columbia with his wife and starts running West Coast operations for the company. He's happy to work outside the spotlight, spending time with his growing family. By the late 70s, he and his wife have two daughters. Conrad takes a different approach. He's in charge of the East Coast side of the company's operations. And it's around this time that he hooks up with a secretary named Joanna, gets her pregnant before her divorce is final, and keeps the kid a secret until after their wedding. But unlike David, Conrad wants more than just a business and a family.
11:31 Scaachi Koul? By this time, he's published a biography of Maurice Duplessis, a far-right politician who was the premier of Quebec in the mid 20th century. Conrad wants to be known as an intellectual and be accepted by the upper echelons of Canadian society. And more importantly, he wants to get invited to exclusive dinner parties. Conrad's ambition is about to drag David and him into a new realm of business dealings that will shock the establishment, pad their pockets, and elevate Conrad, finally, into the high society he's craved for so long.
12:04 Scaachi Koul? It's May 1985, and Conrad is settling into an armchair at a suite in the Hilton Hotel near New York's JFK Airport. He's in his early 40s now and has a reputation as a ruthless businessman. He flew here from Toronto on his corporate jet, which is lined with mahogany and leather. But Conrad won't be the fanciest person at the meeting today. That would be Lord Hartwell, a member of the British aristocracy. Lord Hartwell is in his 70s, with slicked-back hair, glasses, and a penchant for wearing tweed suits. He's a member of the powerful Barry family, which owns a huge swath of the newspapers in the United Kingdom. Their crown jewel is The Telegraph, a right-wing British newspaper revered by politicians and the elite.
12:47 Scaachi Koul? Lord Hartwell's father purchased it in 1927, and Lord Hartwell has run it since 1954. Can you read how he later described his work on the paper?
12:56 Sarah Hagi? Yeah, he says, "I was always terribly shocked when other people ran their newspapers like biscuit factories just to make money. What I was trying to do was make The Telegraph an institution which was respected and admired, and which would leave the world the poorer if it were not there. It sounds awfully boring, but I regarded it as my life's work, that's all."
13:17 Scaachi Koul? I mean, regardless of the results, that is a much better attitude than it seems Conrad Black had when he first bought the paper. Yeah, this is what you want the owner of a newspaper to sound like. But The Telegraph is foundering, and it needs help to stay afloat. And that's what he and Lord Hartwell are discussing today. Conrad negotiates a deal: $14.3 million for a 14% share of The Telegraph. But to really make the most of his investment, Conrad knows he needs to grab the reins fully. So he includes a provision: If The Telegraph sells additional shares in the future, Conrad and David get the first shot at buying them. And six months later, that's exactly what happens. The company is deep in the red, and Conrad says he's willing to pony up more cash in
14:01 Scaachi Koul? exchange for a majority stake in the paper. This would mean the Barry family would be giving up control of the business, but they need this boost if they want the paper to survive. So Lord Hartwell accepts. In the end, they agree on a whopping $43 million for 50% of the voting rights. When Hartwell later announces the steal to the paper's board, he faints and has to be carried out of the room.
14:25 Sarah Hagi? I mean, that is pretty dramatic, but you know, it is his life's work, and it is his biggest passion. Like, it's a thing he is the most excited about.
14:33 Scaachi Koul? Yeah, I'd faint too. Well, now that he's won The Telegraph, it's time for Conrad to get serious about his status as a media mogul. Alongside David, he combines all his media titles into a company known as Hollinger International, and sets up Ravelston, a company he inherited from his father, as its holding company. Now, they have a punchy name and a new company to create a true media empire. And with The Telegraph under his belt, Conrad is poised to rub shoulders with Britain's elite and nab the recognition and acceptance he's always wanted. But Conrad's gonna get far more than he bargained for, because his effort to climb the UK's social ladder is about to be turbocharged with the help of a little romance.
15:15 Scaachi Koul? It's October 1991, and Barbara Emile is attending a lavish dinner party in London at the historic Spencer House in St. James, just down the street from Buckingham Palace. Tonight's party is hosted by none other than Lord Rothschild, the oldest member of the famous Rothschild banking family. Barbara fits right in with this crowd. She's a tall brunette with green eyes and a voluptuous figure. She was born in England and raised in Canada, and now she's a right-wing columnist for The Sunday Times, known for her sly wit and adventurous spirit. Take a look at this picture from the early 1990s, when Barbara was about 50.
15:50 Sarah Hagi? Yeah, you know, she kind of looks like, she looks like a Bond girl. She's wearing a light blue short dress. Tasteful, but sexy.
16:01 Scaachi Koul? Hint of suggestion.
16:02 Sarah Hagi? Um, you'd think she's trying a bit too hard, though, with all that.
16:07 Scaachi Koul? Well, tonight Barbara is doing more gossiping than flirting. She's seated next to Joanna Black, Conrad's wife. She knows Joanna little, enough to have invited her and Conrad to her third wedding, but the two have virtually nothing in common. Joanna's a devout wife and mother. She's converted to Catholicism and is taking it very seriously. But rumor has it, things aren't going great in the Black household, rumors that Joanna quickly confirms. Joanna tells Barbara that, after spending the summer in Toronto, she and the kids are staying in Canada for good. Barbara's a serial dater of powerful bachelors. If she wasn't dating Oscar-winning screenwriter William Goldman, and if Conrad was single, he'd be a prime target. So Barbara feels some duty to warn Joanna about,
16:52 Scaachi Koul? well, women like Barbara. She tells her, quote, "You must come back to England, or you'll lose him." But Joanna responds, "He's losing me."
17:03 Sarah Hagi? Yeah, I would be like, "Excuse me? What do you, what?"
17:07 Scaachi Koul? Yeah, not a girl's girl.
17:08 Sarah Hagi? No, that's a bit of a crazy thing to say to someone.
17:11 Scaachi Koul? Well, after the party, Barbara learns that Joanna has been doing some flirting of her own with a Catholic priest, and they're getting married.
17:20 Sarah Hagi? Stop. Oh, my God, that's, honestly, that's low-key awesome. Good for her. She fleabagged. Damn.
17:28 Scaachi Koul? Well, not long after that, Barbara runs into Conrad again at another fancy cocktail party. This time, he waves her over. They get to talking and Conrad tells her his marriage is over. Their conversation leads to a new friendship. They bond over their shared love of opera. And the more time they spend together, the more smitten Conrad becomes. Barbara pretends not to notice because she's still technically in a relationship. But Barbara can't ignore how good Conrad smells and she likes that he can make her laugh. She also loves riding around in his well-stocked limousine. Most importantly, Conrad makes her feel taken care of, something she always appreciates. After a few months, it's clear that Conrad is crazy about her.
18:12 Scaachi Koul? In fact, he proposes to her before they've even kissed. And while she's still dating William Goldman, Barbara is tempted. But she doesn't want to be Conrad's rebound girl. So she rejects him and tells him that he needs to see a psychiatrist to make sure that he really wants to be with her.
18:31 Sarah Hagi? This is so messy and so deeply crazy. Proposing before even kissing.
18:38 Scaachi Koul? Sending them to a psychiatrist? I'm taking notes.
18:41 Sarah Hagi? You know what? These two match each other's freak.
18:43 Scaachi Koul? Yeah. Well, a day later, Conrad calls Barbara up. The psychiatrist gave him a clean bill of health. He's not having a post-divorce crisis and he refuses to stop fighting for her. So naturally, they begin a relationship. From the start, their courtship is glamorous and star-studded. Conrad takes Barbara to the homes of government officials and wealthy people where she woos them with her natural charisma, especially if they happen to be men. She can't believe how lucky she is. There aren't many eligible bachelors that can fund her lifestyle and are comfortable with a woman in her age range. Of course, Barbara isn't the only one getting a good deal. She's a partner in crime Conrad has always wanted. Well-connected, captivating, charming, the perfect partner for his rise up in the ranks
19:28 Scaachi Koul? of the British elite. And that's exactly what they both intend to do. But it's going to get expensive.
19:37 Scaachi Koul? It's the summer of 1992, and Conrad is sitting in a small, dimly lit, private dining room in one of the most exclusive venues in London. It's called Annabelle's, and it's a members-only club in the wealthy neighborhood of Mayfair. Conrad and about 20 carefully-selected peers are sitting on plush red chairs around a candle-lit table. Barbara and Conrad are hosting this party to celebrate their marriage, held earlier that day at the Chelsea Registry Office. They had a low-key ceremony because Conrad hadn't gotten an annulment yet for his first marriage. But that doesn't mean this dinner party isn't a full-on celebration. Conrad's seated between two of his close friends, former British Prime Minister Margaret Thatcher and Sarah Ferguson, the Duchess of York and wife of Prince Andrew.
20:21 Sarah Hagi? Wow, talk about nightmare blunt rotation. I'm joking, I'm joking, I'm joking.
20:27 Scaachi Koul? No, I think that's right.
20:28 Sarah Hagi? No, I mean, Sarah Ferguson, she's been through a lot. I'm not going to make a huge judgment, but she's married to Prince Andrew. Conrad Black and Margaret Thatcher.
20:39 Scaachi Koul? Those are the three people you see in hell.
20:40 Sarah Hagi? Truly, I was going to say, like, they will know each other in hell.
20:44 Scaachi Koul? Yeah. Well, even with all these big names in the room, Conrad's most concerned about one person: his best friend and business partner, David. He's relieved to find that David and Barbara are getting along tonight, because so far, their relationship has been strained. They fight all the time. Luckily, the dinner is a smash success, and it's only the beginning for Barbara and Conrad. They spend their first year of marriage traveling: dinner with William F. Buckley in New York, a summer in Maine in the home of David Rockefeller, then on to Fiji and Australia. They even hang out with socialite Brooke Astor. And for the Blacks, everything is a networking opportunity. Once they return to London, the pair turn their home into the place to be for opulent dinner parties.
21:29 Scaachi Koul? One of their biggest annual parties is a summer bash that attracts British politicians, business big hitters, and celebrities like Elton John and Candace Bergen. While Conrad isn't exactly known for being charming, he tends to turn conversations into lectures about historical figures. Barbara really knows how to throw a party. She's even referred to as the Cleopatra of Kensington.
21:50 Sarah Hagi? Yeah, okay, that's a lot. But also, you know, this is so classic rich people, where it's like, even when these people get old and rich and have basically everything they want, like, they just want to be around celebrities and creatives.
22:04 Scaachi Koul? It's all they want.
22:05 Sarah Hagi? It's like, you just want to buy being friends with Elton John and Candace Bergen.
22:09 Scaachi Koul? Yeah, of all people. Well, Conrad has finally arrived in London High Society, and he's feeling himself. In 1993, at the age of 49, he releases a memoir, "The Life in Progress." There's just one problem. The world is in the grips of the worst recession since the Great Depression, and the media business is taking a huge hit. If Conrad wants to keep partying, he'll need more cash. In 1994, two years into his marriage, Conrad decides to turn Hollinger into a publicly listed company. He later writes that Hollinger was only publicly traded to make, quote, "cheap use of other people's capital." Of course, going public comes with risk. It means increased scrutiny and open books. But Conrad isn't worried about this.
22:53 Scaachi Koul? With friends in high places and a money man like David, how could anything go wrong? With this new cash flow, Conrad's about to achieve all his dreams: international renown, wealth, and the fanciest friends on earth. But he's gonna do it his way, ruthlessly and at the expense of everyone else.
23:19 Scaachi Koul? Now I feel like a legend.
23:26 Scaachi Koul? The same month that Hollinger goes public, David Radler moves into a $1 million apartment at the Four Seasons in Chicago. By this point, David's hair has turned gray, and he has a permanent tan from spending all of his spare time in Palm Springs. Hollinger has just purchased the Chicago Sun-Times, the ninth-largest daily newspaper in the US by circulation. And David is in Chicago to oversee the takeover. So Hollinger is paying for David and his family to stay for as long as this takes. David's sprawling apartment has a marble bathroom, a huge soaking tub, quartz countertops in the kitchen, and panoramic views of the city. Not too shabby for temporary housing. At this point, David is well-known for cutting costs at his publications. He's been described as a, quote, "union-hating human chainsaw."
24:11 Scaachi Koul? So while he's living in luxury, the Chicago Sun-Times staff is quaking in fear at what's to come.
24:18 Sarah Hagi? Wow. So glad that this doesn't really happen anymore. This is so typical. I'm not surprised. And I feel like he's going to decimate this newspaper.
24:28 Scaachi Koul? Well, also unsurprisingly, journalists hate David. They think he's poison to every newspaper he touches. And when he arrives at the Chicago Sun-Times, they are proven right. David starts by shutting down the office escalator to save in energy costs. Ultimately, the move increases costs because of the extra wear and tear on the building's elevators. Can you read how the paper editor at the time later described David's approach to layoffs?
24:53 Sarah Hagi? Sure. This won't traumatize me at all.
24:55 Scaachi Koul? Yeah, this is actually the trigger warning we should have given you.
24:58 Sarah Hagi? This is the trigger warning we need. He said, "He came into an executive meeting once and threw a sheaf of papers down and said, 'I want 100 people laid off.' We said, 'What are you talking about?' He said, 'There were 100 people off work last week, and we got the paper out without them.' That's the kind of guy he was. He was ruthless."
25:18 Sarah Hagi? Honestly, go to hell. This guy is playing The Sims with people's lives. It's so disgusting. It's so selfish. And I'm rooting for his demise. What can I say?
25:29 Scaachi Koul? Yeah, I think that's right. Well, at this point, Hollinger has been on a bit of a spending spree. It owns some big names in media now, in addition to local outlets. It's all part of a much bigger strategy. Buy up tons of small, local papers and use them to take out the nearest major player. By 1995, Hollinger owns more than 500 newspapers, with a combined circulation of nearly 5 million. As Hollinger gets bigger, David finds new ways to get inventive with the business. Starting in 1997, he inflates the circulation numbers of some of Hollinger's flagship papers by simply dumping all of their unsold copies in the trash. And he uses these inflated numbers to charge advertisers way more money for
26:11 Scaachi Koul? ad placement. Cutting corners to make their businesses more profitable is one thing, but that's not enough for David and Conrad. They start using Ravelston, the holding company for Hollinger, as their own personal piggy bank. They have Hollinger pay Ravelston millions for David and Conrad's, quote, "management services," when the only thing the longtime business partners are doing at Ravelston is collecting checks. And after Barbara allegedly called the Concord "British public transport," Hollinger paid $25 million for a Gulfstream jet that could accommodate the blacks' transatlantic flights.
26:46 Sarah Hagi? Wow. It's one thing to just treat your newspaper like it's meaningless and employees like trash the regular way, but this whole thing of inflating numbers and dumping these unsold copies in the trash, only to be like, "Yeah, we should be buying a better jet." It's a level of evil that really, really gets me.
27:04 Scaachi Koul? Yeah, I mean, he is rich enough and he's scamming to get even richer. But this scheme quickly runs into trouble. David and Conrad's enormous management fees, plus the hit the newspaper industry is taking from a switch to digital content, has Hollinger drowning in debt. And it's debt that needs to be paid off fast. So by the time 1998 rolls around, David is overseeing the sale of 45 of their US-based newspapers to the tune of $475 million, or almost $1 billion in today's money. David's looking for more than a good purchase price, though, so he starts weaving non-compete clauses into all of Hollinger's sale agreements. When a company buys a paper from them, Hollinger agrees not
27:46 Scaachi Koul? to create a competing paper. In exchange, they get a large payout. But most of these papers are so hyper-local that there's no point in competing with them. So Hollinger is making millions of extra dollars for basically doing nothing. On top of this, because of the way that the laws work in Canada, these profits are all tax-free. The money from these bogus deals should be going back to Hollinger, but instead, it's being diverted to Ravelston without the board's knowledge. Conrad and David are secretly squirreling away millions of dollars that should belong to their shareholders, and no one else at Hollinger is the wiser. Hollinger is also footing the bill for David and Conrad's pet interests, like a wing donated
28:27 Scaachi Koul? to Toronto Children's Hospital for Conrad, or a $168,000 donation to David's alma mater, Queen's University, to establish the Radler Business Wing. And in 1998, Conrad buys $18 million worth of stock in Live Ent, the company owned by scamfluencers alum Garth Trabinsky. He made the investment two months before Garth was hit with criminal charges by the Justice Department, and Conrad then personally contributed to Garth's legal defense fund. David isn't as obsessed with status and luxury as Conrad, but he does enjoy the creature comforts that come with all this extra money. He buys a mansion in Vancouver with an indoor swimming pool, builds an 18th century art collection, and takes full advantage of the Hollinger jet.
29:11 Scaachi Koul? He uses it regularly to fly to Israel, where his daughter works at the Jerusalem Post, which is owned by Hollinger. David and Conrad have transformed the way they use Hollinger. Now, they see it more as their own personal piggy bank, but it won't be long before their shareholders start to notice their unsavory schemes.
29:32 Scaachi Koul? It's December 2000, and Conrad is beaming at a crowd of New York's finest. He's thrown a hell of a party for Barbara's 60th birthday. There are nearly 100 guests, and the party is held at an exclusive French restaurant in Manhattan. On the menu: Beluga caviar, lobster ceviche, veal, and beef carpaccio, paired with Dom Perignon. Conrad's seated next to a famous drag performer and American royalty, a Ford and a Rothschild. There are six billionaires in attendance, as well as Jeffrey Epstein.
30:03 Sarah Hagi? Wow. You don't say Jeffrey Epstein was at at least one of his parties. Huh. Wonder what their relationship was like. Probably super innocent.
30:14 Scaachi Koul? They just had money talk.
30:16 Sarah Hagi? Yeah.
30:16 Scaachi Koul? He was a financier.
30:17 Sarah Hagi? It was just about going on jets and stuff.
30:19 Scaachi Koul? Yeah.
30:19 Sarah Hagi? Talking about cash.
30:20 Scaachi Koul? Well, at the end of the night, the bill comes. They spent 13 grand on just the wine. The total for the night is more than $62,000. But Conrad's not worried. He charges most of it back to Hollinger as a business expense, because hey, he's networking. As happy as he is to treat his wife, Conrad's also celebrating how far he's come. He started working on a new biography about his beloved FDR. He's finally holding court among some of the most powerful people in the world, and they're hanging on to his every word. He can talk about Napoleon as much as he wants.
30:56 Sarah Hagi? It is just so crazy how all these guys like this have an obsession with Napoleon. You know, maybe it doesn't mean anything, but it's usually a sign of a guy who is batshit.
31:07 Scaachi Koul? Well, all of Conrad's socializing is paying off. His circle of friends worships him and Barbara. The pair are living out of a premium apartment in Manhattan, and Conrad uses Hollinger funds to furnish it. So far, Hollinger's paid for a $12,000 vanity stand and a shaving bottle once owned by Napoleon. But Conrad's not worried about his insane spending or how it might look. He has his sights set on something bigger. He's about to follow in the footsteps of many shady businessmen before him and become a member of the British aristocracy.
31:41 Scaachi Koul? It's Halloween 2001, and Conrad gleefully waits in a red leather seat in the House of Lords. When his name is called, he stands up and walks, with Margaret Thatcher at his side, towards a man in ridiculous British legal garb, a puffed black robe and an enormous curly white wig. Conrad is in a robe of his own, too, and he's feeling regal. Because Conrad is being entered into the House of Lords, a privilege reserved for British aristocracy and businessmen with the right connections. This group includes the highest of British elites, and they have actual power over political decisions in the UK. Now Conrad is one of them. Conrad signs his name and turns to wave at his friends in the visitors' galley, Barbara and Henry Kissinger.
32:25 Scaachi Koul? He's now Lord Black of Cross Harbor, named for the station next to the Daily Telegraph's newsroom. He'll have the right to vote on issues that reach the House of Lords, like new laws or issues in government.
32:37 Sarah Hagi? It's so hard to process this because he's always around the most evil people in the world. And now, outside of having power from just owning newspapers and being able to control the news, now he has this position that actually changes things on a legal level, right?
32:54 Scaachi Koul? Yeah, he's really extending his influence. And Conrad's hopeful that his new title of lord will get him noticed in New York, where he's still a small fish in a big billionaire pond. He's doing well in London, clearly. But the power in the UK isn't enough for him. Being powerful in America means you're powerful everywhere. He wants a seat at that table, but he isn't rich enough yet. So in the meantime, at least he has a cool new name.
33:20 Sarah Hagi? My god, get over it. You're a grown ass man. You're rich. It's so pathetic, but also so Canadian.
33:28 Scaachi Koul? Real Canadian inferiority complex. But in the meantime, Conrad and Barbara are really living it up. They bounce between their homes in London, New York, and Florida, regularly traveling across the Atlantic by private jet, often at Hollinger's expense. Like, at the end of 2001, perhaps to celebrate Conrad's lordship, they take a trip to Bora Bora that costs more than half a million dollars. And they bill Hollinger for the use of the jet, complete with a brief stop in Seattle to go to the opera. Conrad also has Hollinger pay $8 million for a cache of FDR papers, research for his latest book, letters that he then puts on display in his own home.
34:08 Scaachi Koul? These are all bold moves for a man whose company is struggling. Conrad and David have spent the last year selling off many of their publications, largely to cope with Hollinger's mysteriously rising debt. It doesn't help that Conrad uses these frequent restructuring opportunities to steal even more money. He charges Hollinger $30 million for his services as a manager that year alone. All of these fees go straight to Ravelstine and into Conrad's pocket, without anything saved for taxes or Hollinger shareholders. David, as a joint owner of the company, likely gets some money from this, too. But Conrad isn't worried. Even after all this time, he doesn't think anyone notices what he's doing. But a former reporter is already on his tail, and it's only a matter of time before she exposes him.
34:54 Scaachi Koul? In 2001, while Conrad's having the time of his life as a newly minted lord, journalist Laura Jureski is enjoying her recent career shift. She'd been a dogged investigative journalist at places like The Wall Street Journal, but a few years ago, she decided to take a more lucrative role as a stock analyst at a big-time investment firm called Tweedy, Brown & Company. As an analyst, Laura's job is to examine the companies the firm invests in. She had actually recommended that Tweedy invest in Hollinger a few years ago, and the firm now owns an 18% share of Hollinger, Inc. But Laura has noticed the disparity between Conrad's lifestyle and the dire financial situation at his company. By the early 2000s, Hollinger's stock price is almost half of what it was when the company went public.
35:36 Scaachi Koul? They were forced to unload $2.2 billion in assets just to stay afloat. But according to Hollinger's public announcements, annual revenues have topped $2 billion for four years running.
35:48 Scaachi Koul? As a former journalist, Laura knows that newsrooms can eat money. Plus, some of this can be explained by the state of the industry. Newspaper advertising has been drying up, but that still doesn't explain why the company is in so much debt. There has to be a hole to plug somewhere, because the company is leaking money. So Laura decides to start digging, and she stumbles upon something huge. As the executive directors of Hollinger, Conrad and David are collecting tens of millions of dollars from the sale of their newspapers, thanks to those lofty, non-compete agreements. But this money isn't supposed to be going to them. It's supposed to be going to the company's shareholders. The two men are stealing from their investors and shareholders in plain sight, and Laura seems to be the first person to notice.
36:32 Scaachi Koul? Laura decides she can't let this stand, so she writes to Conrad and gets no response. But she doesn't give up. Instead, she spends an entire year writing and emailing Conrad, demanding answers about the money he's skimming from his company. She even starts a letter-writing campaign to Hollinger's board of directors, but every letter goes unanswered. No one is willing to talk to her. And maybe that's because the board of directors is mostly made up of men like Henry Kissinger, who are technically on the board but rarely attend meetings.
37:01 Sarah Hagi? Oh my god. This is really a classic tale of one person wondering what's up and uncovering an entire scam. It is pretty crazy that she was the only one to figure out that they're skimming from their shareholders. Like, I don't get how no one else cares.
37:20 Scaachi Koul? Yeah, I'm always amazed at how little people care about stuff. Well, Laura doesn't know it yet, but Conrad is reading her emails, every single one of them. He's even been drafting responses, but instead of sending them to Laura, he's circulating them to his cronies, mocking her behind her back. He uses subject lines like "epidemic of shareholder idiocy," and even starts referring to Laura as a rottweiler. But as far as Laura knows, she's being completely ignored, and she's stuck standing by as Conrad continues to earn millions of dollars. In 2002, he pays himself over $400,000 from The Telegraph in London and receives another $248,000 just for attending Hollinger's board meetings.
38:01 Scaachi Koul? Around this time, Laura's boss at Tweedy, Brown & Company gets involved. He tries to drum up the support of other shareholders to go after Conrad, but their fund owns less than one-fifth of the company. Getting support, even with Laura's figures, isn't easy.
38:18 Scaachi Koul? Then comes the golden gun. In August 2002, the new issue of Vogue hits newsstands. It features a lengthy profile of Barbara, along with a photo shoot at their London home. She gives a journalist a tour of her many closets, one for furs, one for sweaters, one for t-shirts, and one so crammed full of evening gowns that extras have to be kept in overflow closets downstairs. She also shows off more than a dozen Birkin bags and over 100 pairs of Manolo Blahnik shoes. She proudly tells the journalist that she possesses, quote, "an extravagance that knows no bounds."
38:52 Sarah Hagi? This kind of happens with Vogue sometimes, be it Vogue weddings, or these profiles of wives, literally just wives, where they think like, oh, this is great, like, I've made it. I'm in the pages of Vogue. I was selected, for whatever reason. But they don't know they're doing something incriminating.
39:10 Scaachi Koul? Yeah, she's hiding in plain sight in this very ugly dress. And when Laura sees the article, she's probably thrilled. There is no way the Blacks can afford everything in this photo spread with his posted salary alone. It shouldn't be hard to whip up Conrad's investors into a frenzy to finally get answers about his spending and the company's finances. By May 2003, Laura's hard work finally pays off. Tweety Brown and Company files a complaint with the SEC, demanding that Hollinger's board investigate the payments Laura found to Conrad's accounts. A special committee of Hollinger directors is assembled to oversee the investigation. They pore over the documents Laura compiled, comb through the murky financial structure that David and Conrad set up, and start to trace the flow of money through Hollinger.
39:55 Scaachi Koul? By the end of the investigation, the group estimates that nearly $400 million was stolen from the company over seven years. That's nearly all of Hollinger's profits from this period.
40:06 Sarah Hagi? When I think about someone like Conrad Black, you kind of wonder, like, what does he actually care about? He obviously wants to have an image of a guy who knows a lot about history and can write a book on FDR and knows a lot about Napoleon, but he also doesn't look at history for any type of lesson, it seems.
40:25 Scaachi Koul? No, he doesn't think that he needs to learn anything at all.
40:28 Sarah Hagi? No, it's like the oddest status symbol. Just be cool and you won't have to do all that.
40:33 Scaachi Koul? While Laura's many years of tireless work do more than just ruin Conrad's book tour, because of her efforts, Conrad and David could be facing millions of dollars in fines and repayments, and maybe even jail time. Under intense pressure from the board and the media, David resigns from his role at Hollinger at the end of 2003. Conrad follows suit a year later. But immediately after, he sues the Hollinger International Committee for $1.1 billion, claiming they defamed him. But Laura probably isn't worried about any fallout. Everyone involved knows Conrad doesn't have a leg to stand on. He's just trying to buy more time by tangling them up in expensive legal battles. The defamation suit eventually reaches the Supreme Court of Canada over jurisdictional issues, where Conrad is successful.
41:18 Scaachi Koul? The lawsuit is ultimately settled out of court for a substantial sum. For Conrad, this strategy seems clear. As long as he can keep the fight alive, loudly and publicly, he can cast doubt, muddy the waters, and maybe preserve enough credibility to maintain his reputation. But this window is closing fast, because a traitor is about to emerge from Hollinger's ranks.
41:52 Scaachi Koul? It's April 2004, and David's feeling vindicated. He's spent his whole life being careful with his wealth and staying away from the limelight that Conrad craves. While the whole world is watching his former business partner, he's been mostly left out of the spotlight, which gave him time to figure out his next move. And he's decided to bet it all against Conrad. David is nervous. But when his lawyer approaches federal investigators, they say they're willing to strike a deal with him. If he cooperates and helps to incriminate Conrad, they'll give him a lighter sentence.
42:24 Scaachi Koul? David does have mixed emotions about this deal. He can't help but feel guilty for throwing Conrad under the bus. They've built empires together, and they've both been stealing money. But if David doesn't save himself first, the blacks will come for him eventually, especially Barbara. She's never liked him anyway. The next month, Conrad is caught on camera taking documents out of the Hollinger offices. Remember this from the beginning of the episode? This little stunt prompted allegations that Conrad was obstructing justice on top of everything else. David might feel a little vindicated reading about his friend's desperate and very stupid ploy. David may have been a figure behind the scenes as he and Conrad built their incredible media empire, but he's about to step firmly into the spotlight as the US government star witness
43:09 Scaachi Koul? in taking Conrad down. But as David likely suspects, his old friend and business partner is not going down without a fight. Seven months after David starts cooperating with the US government, federal prosecutors indict Conrad for cheating shareholders and withholding taxes in Canada. The Justice Department, the SEC, and a newspaper company owned by Hollinger are seeking more than $1.5 billion in damages from Conrad and other executives. He and Barbara sell their homes in New York and London. In August 2006, Conrad is getting ready to celebrate his 62nd birthday with a dinner at his mansion in Toronto, but festivities are seriously dampened when a legal order comes down, freezing his assets.
43:53 Scaachi Koul? Earlier in the summer, Conrad told the court that he and Barbara spent an average of about $200,000 a month on reasonable expenses. Now, everything from his catering expenses to his butler's salary has to be pre-approved, and the judge is putting the blacks on a serious budget. They can only spend around $22,000 a month.
44:13 Sarah Hagi? Oh my god, that's nothing. What the hell are you supposed to do with that? $22,000 a month? Okay, what, you'll get your nails done and go to a movie?
44:21 Scaachi Koul? Chump change. Well, six months later, in March 2007, Conrad walks up to a large, black, imposing building, the US District Court of Northern Illinois. In the courtroom, Barbara and his 24-year-old daughter from his first marriage sit behind him. Conrad is pretty sure he's gonna win. He even released an opinion piece in The National Post in Canada just before the trial started. It was titled, "I Am Not Afraid."
44:48 Sarah Hagi? And this is the newspaper he owns and is stealing from, right?
44:53 Scaachi Koul? On the list.
44:55 Sarah Hagi? What a guy.
44:57 Scaachi Koul? But the prosecution's opening statement doesn't pull punches. They've created huge graphics to help the jury deconstruct Hollinger's convoluted corporate structure. They accuse Conrad of being just like a bank robber, but in a suit instead of a balaclava. And Conrad isn't helping his own defense. He smirks openly when his emails are put on display for the courtroom. Then, in May, David finally takes the stand. And when he enters the witness box, he makes a real show of it. Onlookers describe him as a forlorn and remorseful criminal, walking slowly into the courtroom with his head bowed. But David's also wearing a bright pink tie and his incredibly suntan. Plus, he's wearing loafers. Despite the turmoil he's faced over betraying his ex-bus friend,
45:41 Scaachi Koul? David seems relaxed and is even smiling. He tells the jury that Conrad had oversight over every financial decision that they made at Hollinger. He was well aware of every dodgy charge and transaction. And later that month, the prosecution put a cherry on top of David's damning testimony by playing the CCTV footage of Conrad stealing all those boxes of documents from the Hollinger office.
46:04 Sarah Hagi? Now that we've gotten to the point where that is revealed to the court, it is genuinely so surprising that he physically went and did that and didn't hire someone to scope out the area, figure out if there was other surveillance. It just seems like such a stupid mistake.
46:23 Scaachi Koul? Yeah, it's a lot of unforced errors across the board on this story. But on the bright side, Conrad does have some things going for him, like his loyal wife, who hasn't left his side since the trial began. But Barbara's not exactly doing him any favors at the moment. Conrad always thought she had one fatal flaw: her anger, which she struggles to control. And unfortunately, she's now releasing it on anyone she considers to be the enemy. She's even actively attacking journalists reporting on the case. In one incident, she cornered some of them in an elevator and called them sluts and vermin.
46:58 Sarah Hagi? That is honestly...
47:01 Scaachi Koul? It's hard not to root for her.
47:02 Sarah Hagi? It's hard. No, okay, whoa, I'm not rooting for her.
47:05 Scaachi Koul? Not to root for her, but you know what I mean. Like, I do want to write everything she says down in my diary.
47:10 Sarah Hagi? She's definitely a character. She is very amusing, and it's so funny to be like, "You sluts, vermin."
47:18 Scaachi Koul? In 2007.
47:20 Sarah Hagi? And also, you know, she's angry, and the only person to blame is her husband. And yet, she's angry at everyone else.
47:27 Scaachi Koul? Yeah. Well, her husband does have a lot of supporters, at least 100 of them, including Elton John, who have written to the court and requested that Conrad get a lenient sentence. In August 2007, Conrad is found guilty on three counts of fraud and one for obstruction of justice. He'll face a debt of $6.1 million to his shareholders, significantly less than the $30 million the US government originally aimed for. Four months later, Conrad is sentenced to six and a half years. During this time, Barbara writes articles about how Conrad's trial has exposed gross defects in the American justice system. Sarah, can you read this quote from her 2020 memoir on the subject?
48:05 Sarah Hagi? Yeah, she says, "The only revenge would be to see our persecutors guillotined. I have worked out 1,001 ways to see them die, beginning with injecting them with the Ebola virus and watching." What? Okay, she is... Calm down, sister.
48:21 Scaachi Koul? It's crazy that they publish this.
48:23 Sarah Hagi? When people are operating from a place of a totally different reality, like, what can you even say?
48:28 Scaachi Koul? Yeah. Well, after all this, Conrad reports to a Miami prison in March 2008. And he actually has a blast in prison. He keeps a journal in French. He befriends some Colombian inmates who make him expertly brewed coffee. He tutors young people on day trips outside the prison and gives history lectures. He meets friends for lunch, and he gets to play the piano every day. He gets back to writing his column in The National Post and The Daily Beast and The National Review. During his time in prison, Conrad earns so much respect from his fellow prisoners that they sometimes salute him when he joins them for class. He also has an entourage of jailmates who mop his floors, iron his clothes, and do other menial tasks for him. Though essentially, he learned nothing.
49:13 Scaachi Koul? In 2011, while he's still behind bars, Conrad releases another memoir, A Matter of Principle. He gets blurbs from Alan Dershowitz, George F. Will, and Rush Limbaugh.
49:25 Sarah Hagi? Yeah, I mean, likely place for them to be. It is scum of the earth.
49:30 Scaachi Koul? Scum meets scum.
49:31 Sarah Hagi? I can't believe how many times Alan Dershowitz makes an appearance in this show.
49:36 Scaachi Koul? It's basically, this is his show.
49:38 Sarah Hagi? I truly hope they are all reunited in hell. I don't know what else to say.
49:42 Scaachi Koul? Well, Sarah, I know you know some of the rest. In May 2012, Conrad is released from prison after serving about three years. He returns to Canada and reclaims a citizenship. And he gets right back to work. He starts hosting a talk show called The Zoomer, where he interviews right-wing figures like Boris Johnson and Donald Trump. In fact, he and Donald are still so close that Conrad writes his 2018 biography, Donald J. Trump: A President Like No Other. One year later, in May 2019, Donald Trump pardons Conrad for his crimes. Conrad never takes accountability for what he did. A few months after his pardon, he writes in his National Post column, quote, "My long ordeal with the US justice system was never anything but a confluence of unlucky events."
50:26 Scaachi Koul? Even though those events include being convicted of skimming money off the top of his company, as far as Conrad's concerned, he's always been in the right. And it seems like no matter what misdeeds you commit, having friends in high places always pays off.
50:43 Scaachi Koul? Sarah, a brutal one today. Always hard when we have to talk about someone whose scam we witnessed in real time and we were directly impacted by it. Because you and I wrote for a lot of different newspapers that were owned by Conrad Black. It's funny to think of Conrad Black as the early architect of the demise of Canadian print media, but I guess he did almost single-handedly destroy newspapers.
51:04 Sarah Hagi? He did, and it's so upsetting when everyone's like, who could have possibly known that everything would turn out this way? And you're like, everyone could have. People like him are smart enough to implicate enough powerful people in their crimes, both the known and unknown ones, that anyone with power would have to be a class traitor to actually punish him.
51:27 Scaachi Koul? He was also just such a deeply unpleasant and odious public figure. It seemed like he rejoiced when life was harder for marginalized people. So it wasn't just that he's like stealing money from this company, from all of his companies, or that he's killing the paper. It's that he also was gleeful about being an asshole.
51:46 Sarah Hagi? Yes, of course. And when someone's humbled, a lot of the times, they end up not trying to get in the spotlight in the same way, or maybe rehabilitate their image in some way. But he truly did not.
51:59 Scaachi Koul? We have a lot of scammers who do stuff like this, and it's not like we're saying, yes, you should do fraud. But it is at least a little more understanding when you come from fucking nothing and you're trying to get a taste of this high life that you've never had access to. This is someone who will always have access to it, no matter what. He was always going to be in those rooms. It's just a question of whether or not people had to kiss his ass or not.
52:22 Sarah Hagi? We have these episodes also where I feel so grateful for my stupid, normal life. And this is one of those where I'm like, I could never, in my wildest dreams, want this because it's so disgusting to me.
52:34 Scaachi Koul? I'm glad that I have no taste for a private jet.
52:36 Sarah Hagi? No, not at all. I mean, hey, but if you got one, I will sit on it if it's going somewhere anyway. I'm not going to say no.
52:42 Scaachi Koul? Yeah, I guess the lesson is, I would never charter a jet, but I'm open to a seat.
52:47 Sarah Hagi? I would, yeah, put me on a seat, put me on the jet. If there's a seat there, I'm just going to sit there. I'm just going from point A to point B.
52:54 Scaachi Koul? No blood on these hands.
52:56 Sarah Hagi? No, no, not at all.
53:06 Scaachi Koul? This is Conrad Black, The Fleet Street Fleece. I'm Sachi Cole. And I'm Sarah Haggy. If you have a tip for us on a story that you think we should cover, please email us at [email protected] . We use many sources in our research. A few that were particularly helpful were Shades of Black: Conrad Black, His Rise and Fall by Robert Seklos, Friends and Enemies by Barbara Amiel, A Life in Progress by Conrad Black, and reporting by Edward Klein, Maureen Orth, and Duff MacDonald for Vanity Fair. Jessica Lucas wrote this episode. Additional writing by us, Sachi Cole and Sarah Haggy. Olivia Bryle is our story editor. Fact checking by Lexi Peery. Sound design by James Morgan. Additional audio assistance provided by Augustine Lim.
53:49 Scaachi Koul? Our music supervisor is Scott Velazquez for Freeze on Sync. Our managing producer is Desi Blalock. Our senior managing producer is Callum Pluse. Janine Cornolo and Stephanie Jens are development producers. Our associate producer is Charlotte Miller. Our producer is Julie McGruder. Our senior producers are Sarah Enney and Ginny Bloom. Our executive producers are Jenny Lauer Beckman, Marshall Louie, and Aaron O'Flaherty. For Wondery. Follow Scamfluencers on the Audible app or wherever you get your podcasts. You can listen to all episodes of Scamfluencers ad-free by joining Audible.
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