Ian Mitchell: The Man with Two Names

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1:32You never think it's someone you know. Whether it's horrible tragedies, legal issues, or national headlines. Those are things that happen to other people. Not somebody in your own orbit. But for real estate agent Terrence Harding, it was. The morning of Wednesday, March 22, 2023, was crisp and cool in New York City. But in Midtown Manhattan, it took no time at all for the day to fall completely off the rails. It started with shattered glass clinking to the sidewalk on West 56th Street. A man threatened to jump from a high-rise building in Midtown. By 8.40 a.m., a crowd had gathered in front of the shimmering postmodern City Spire building.

2:21A man had smashed his condo window and climbed out onto the ledge, and the FBI was right behind him. As authorities tried to get into the apartment, the man tiptoed further out onto the ledge, warning that he'd jump if they came any closer. The crowd underneath grew with every passing minute. You can see him there, 31 stories up, just sitting in a broken window. The tent scene captivated the unflappable city. Even then-Mayor Eric Adams arrived on site. Meanwhile, the New York Fire Department laid down an air cushion in the middle of the street, in case the worst happened. But while it was an anonymous piece of urban drama for many, for others, it was deeply personal.

3:14While I was at work, Terrence texted me and he's like, hey man did you see that guy hanging out of the skyscraper i'm like yeah he's like i know that guy terrence had recognized him immediately oh shoot this is ian terrence tracked the scene as his client ian madelon played cat and mouse with the fbi and nypd he watched and watched and watched some more because the standoff didn't end for over eight hours when the NYPD broke the window of a floor above, rappelling down the side of the building, and kicked Madelon back inside. That's like out of a movie there. Yeah, a lot of people. Incredible to watch that.

4:00The show may have been over, but the story was anything but. New York was only beginning to cope with the aftermath. Forget about the skyscraper standoff. What did the FBI want with Mitchell to begin with? None of it made any sense. This was the same man that Terrence had worked with for over a year, with zero red flags. They'd eaten together, drank together, done business together, and Ian never once asked Terrence for a thing. He was cool, smart, talented, wealthy, and generous. So what on earth could his client have gotten himself into? And more importantly, why was the news calling him by a different name?

4:54This is The Opportunist, an original podcast from Podcast One. I'm Sarah James McLaughlin. Today we're telling the story of Ian Mitchell and how his year of touring luxury penthouses has left real estate agent Terrence Harding with questions he'll never be able to answer. It's a mystery that we're still unpacking over three years later. And even now, we may be no closer to a motive.

5:35Terrence Harding is not your average real estate agent. Prior to becoming licensed, the smooth-talking 49-year-old, often seen in a three-piece suit, was a rapper, with Notorious B.I.G.'s hit group Junior Mafia. After feeling frustrated with unfair record contracts, he pivoted to a new career where his talents and ambition could be better appreciated. He received his real estate license in 2006 and joined the firm Mark David & Company. By 2007, he was one of its top agents. The Brooklyn native understood New York City and the wants and needs of its upper class from his rap days. In 2016, he founded the hard-cost team at Compass Real Estate, which focuses specifically on the New York market.

6:27He knows the game and he knows the players. So when Ian Madelon of Jamaica reached out to him in November 2017, Terrence was able to recognize all the signs of a serious buyer. The first sign? The name. The Madelon family and their business ICD Group has been a hugely successful private equity investment company in Jamaica since the 1910s. But it didn't start that way. Joseph Madelon, a Syrian Jewish man from Damascus, started his new life in Jamaica with mixed results. After marrying local Florizel Henrique, Madelon went on to have 11 children. But Joseph's early business ventures failed, resulting in son Aaron having to leave Jamaica College to help ends meet at only 13 years old.

7:22Things changed for the Madelons following World War II. Joseph and his now adult children helped to successfully build the first post-colonial housing development on the island. And as the children continued to grow and thrive, their influence extended beyond the world of industry. Eli Madelon served as the mayor of Kingston from 1971 to 1973. His brother, Mayor Madelon, helped the ICD group skyrocket while creating mass affordable housing for working-class Jamaicans. He'd even go on to serve as an advisor to the prime minister. By the second half of the 20th century, the Madelons were well known by entrepreneurs worldwide.

8:06Today, ICD's president is on the board of the Sandals resort chain, and the Madelons have had big plans for developing resorts of their own on the island. Ian's identity as a Madelon didn't just mean he had money. It meant he knew real estate too, and not just its value monetarily, but equally importantly, as a cultural signifier. By this point, Ian was now the manager of his family's hedge fund, and he demonstrated the exact connections and know-how you'd expect out of someone with that background. Right from the very first meeting, Madelon wasn't afraid to lean on his family's position.

8:48Ian Mitchell:He pulled out and showed us what they were creating and like, look, we gotta go down there, and we're going to go see it. And I can't wait to take you guys there. You guys are like, this is what we're building out. But even more important than the Jamaica connections, Madelon knew New York, just like Terrence did. Ciprianis, Il Molino, Mercer Kitchen, the Peninsula. Madelon ran in legitimate New York elite circles. We knew all the people from Ciprianis. We knew all these different crowds there and the owners. and the people who ran everything there. So we would meet up. He liked El Molino. So we'll go sit down at El Molino, and he'll have drinks, and we'll talk, and just talk about the market and things like that.

9:37Madelon had a private driver and a beautiful clothing stylist girlfriend named Natasha Quiros. To Terrence and his business partner, Deanne Costa, he fit right in.

9:48Ian Mitchell:Not to do my own horn, I'm smooth too, but he was really, really smooth with everything that he did. Ian moved like James Bond. He was so cool, you know, so calm. Like, he really embodied the role of, like, this really suave, like, rich luxury real estate buyer. That's Harrison Connery, a real estate and markets reporter with Ninefin. But Madelon wasn't just Flash. He really knew his stuff, from real estate to New York power players. Most of the times it was me, him and her. And then we'll talk about the market and just talk about the properties and just kind of like the environment that we would be in.

10:30Ian Mitchell:It would be other people that we know, like in Molino, there'll be a bunch of different people around. And we know everybody there. At the end of each night, Madelon would never ask for anything. He even covered the tab. Ian would pick up the check. So he was like spending money on this. I don't remember paying for anything. Madelon was in the market to buy a luxury penthouse. So he and Terrence worked together to locate options that might be a good fit. Then they toured some of the most in-demand properties in Manhattan. The first one was in Soho. The first one was on Wooster with an agent that I know, Emily Bear.

11:10Ian Mitchell:She was really cool. So she had a penthouse. So we met with him like we did with clients and took him to see the penthouse at Wooster. It was exactly what the hedge fund manager was looking for. He fell in love with it. We put in an offer. The offer Terrence is referring to,$35 million. It was a deal. That was the first offer that he tried to put in. This is incredible. The process had been simple and smooth. A happy customer served, and a very nice commission. until an issue arose from the seller's side. The contracts went out, and he was supposed to get it, and they misquoted some sort of number, if I'm not mistaken, and he decided to not move forward with it anymore.

12:04Ian Mitchell:So we continued to show him stuff. 87 Mercer, 42 Crosby, a series of lower Manhattan penthouses and condos, all over$25 million, and all extremely promising. Those were some of the most in-demand properties in the entire city. When Fox 5 New York tracked the most expensive neighborhoods in the five boroughs, seven of the top ten areas were all over Lower Manhattan. Soho, home to both 87 Mercer and 42 Crosby, was number three overall. Situated close to the Financial District, Brooklyn and Greenwich Village, With many of the trendiest restaurants, bars, nightlife, and entertainment in the country, Lower Manhattan was the place to be.

12:54Properties like these are so hot, even that today the city is witnessing record numbers of wealthy renters. There are simply too many millionaires and billionaires vying for the same limited number of units that many are unable to buy, even with all the money in the world. According to CNBC, the number of apartments renting for more than$50 ,000 a month more than doubled from 2025 to 2026. The number of apartments renting for more than$100 ,000 a month has multiplied by 7. These renters are constantly keeping their eyes open for properties to purchase, properties just like 87 Mercer and 42 Crosby.

13:40This was the market trend emerging when Madelon was looking only a few years earlier. A buyer like him flush with cash and actual available units in a go-to neighborhood was a match made in heaven, one his peers could only dream of. So it was no surprise that after touring these properties, deals started to come together extremely quickly. Madelon began bringing in his contractors, well-known vetted craftsmen for New York's rich and famous, to conduct thorough inspections. He and Natasha even began meeting with interior designers to start planning the decor. Everything was falling into place. But in the end, Madelon pulled out of each of those sales as well.

14:26On the 87 Mercer Co-op, for example, he claimed the seller had misquoted their shares. In others, the kitchen was too small, or there wasn't enough outdoor space. But according to Terrence, that's typical in the high-end real estate business. At these price points, there's a whole other level of scrutiny.

14:48Ian Mitchell:When you're dealing with somebody that's trying to buy something for that magnitude of money, every little detail is important. And he pretty much followed the normal protocol of what a high-end buyer would do. So Terrence wasn't frustrated. Of course, a sale would have been nice. But in the meantime, these tours were getting Terrence exposure to top-of-industry properties and agents. I got to see some amazing properties, as crazy as that sounds. And for my level, my business, that's always a great thing. Plus, Terrence was plenty busy apart from Madeline. His hard-cost team always had clients in the pipeline.

15:35Ian Mitchell:So it was just like, okay, well, if he comes around and gets something, we're here. So the dinners, drinks, and tours continued every so often while Terrence worked with other clients. But eventually, the properties and Madeline's price range began to dwindle. Soon, there weren't any more options available on the market. When somebody's looking for something for$25 million and above, there's not a lot out there. Terrence and Madeline kept flagging new leads to each other over the next few months. On October 22, 2018, Terrence sent him a luxury townhouse from one of his owners listed at$18 million.

16:16But this time, after over a year of working together, Terrence never heard back. The very next time he saw Madelon's name, three months later, in the New York Post.

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19:35Until a few months later, when none other than Madelon popped up in a headline for the New York Post. That headline? Con man scammed investors over$100 ,000 at Manhattan parties. This was barely 90 days after Terrence and his client last spoke.

19:56Ian Mitchell:So we were on the tail end of his craziness run. Terrence couldn't believe it. How could this be the same smart, calm, reasonable man he'd worked with for over a year? And what could this model client have done to get in this situation? The truth leaves more questions than answers. And it begins with a check. Here's Harrison Connery, a reporter at Ninefin. The scheme, so to speak, kind of unraveled when one of his checks bounced. He'd written a check to a real estate attorney and it bounced. Then he just kind of ghosted Terrence, from what I remember, after that, because I guess he thought the jig was up.

20:42The jig? Fraud. On a massive scale. Over$700 ,000 worth, to be exact. During the same time when he was working with Terrence, Madelon was using his family's position to lure people into faulty investments. In one case, he tricked an acquaintance into giving him$200 ,000 for him to invest in a cannabis business through the family. In another, Madelon solicited over$500 ,000 out of several victims by pretending he had a special access to pre-IPO offerings on companies like WeWork and Dropbox. His targets included everyone from restaurateurs to Air Force veterans, anyone with money he could meet through a mutual connection.

21:30In each of these cases, the opportunity was completely made up. Madelon understood the reputation and inherent trust that came with proximity to wealth like his. And he decided to take advantage of it. And that leads us to the biggest lie of them all. There is no Ian Madelon. He had everybody fooled. Ian Madelon was actually Ian Mitchell. And he had no more connection to the real Madelon family than you or I. But between his research and his charm, nobody was the wiser. Not even Terrence.

22:10Ian Mitchell:He had to embody this persona in order to get little bits and pieces of money from various individuals. So it's like it all had to interconnect like a spider web. He truly did embody the fake Madelon in every aspect. both physical and mental, all down to the tiniest details. He knew how to talk to folks. You know, he knew how to socialize, knew how to dress the part. He knew what to say. He knew how to carry himself and carry himself in such a way where you couldn't tell that he wasn't who he said he was. Almost like Leonardo DiCaprio in Catch Me If You Can. He sold it very well, and he sold it to people that, like myself, were used to being around people that moved that way.

23:03Ian Mitchell:So he played the part exceptionally well. Mitchell had convinced everyone he was Madeline, and he did it through all of his relationships. He only ate at elite restaurants, only worked with luxury contractors, and only went out with high net worth friends and acquaintances. It wasn't like he was just dealing with the average Joe Smoles and Mary's out there. He was dealing with people that were used to doing stuff. So that's why it kind of caught me off guard as well, because I don't usually get doofed. And perhaps most shocking was that the false identity wasn't just for professional purposes.

23:46It was social, too. Remember Natasha Kuros, the clothing stylist's girlfriend? She was just as shocked as everyone else. Mitchell stole$70 ,000 from her and her family. And she only found out when he was arrested.

24:05Ian Mitchell:Apparently, from what I was reading in other articles, she didn't know. So think about that. Imagine you have a boyfriend and they were like living together. An entire life, completely fabricated. and paid for through the so-called investments he was facilitating. Obviously, Mitchell could never afford the kind of properties Terrence was showing him. Not even was his three-quarters of a million in stolen money. Instead, Mitchell used his haul to fund his luxurious appearances. The driver, the meals, the drinks. He was just stalling on the penthouse, at least for now. And the relationships he formed along the way made maintaining Ian Madelon even easier.

24:55Each new friend and colleague opened up an entire new network of potential victims. But if Mitchell was good, he wasn't perfect. Investors started to become suspicious at their lack of returns. And when Mitchell became slower to respond, they began to notify the authorities. By the time Mitchell first met Terrence in 2017, the law was already on his tail. Earlier that year, Mitchell had been arrested on counts of grand larceny before being released on bond. The entire time he was out on the town touring penthouses, Mitchell was bail jumping, skipping out on his court appearances, staying just one step ahead of another arrest.

25:42He remained that step ahead for six years, even after the additional arrest in 2019. Until he ran out of rope in March 2023, when the FBI tracked him down to the 31st floor of the city spire building in Midtown. They had a warrant with them for alleged wire fraud. Mitchell was cornered, so he turned to the only other way out of the apartment. The window. He smashed the glass and climbed out onto the ledge, calling back to the FBI hovering in the hallway that he'd jump if they came any closer. It just kind of went viral because it was kind of a crazy news story. Of course, Mitchell had only delayed the inevitable.

26:27He kept the FBI at bay late into the afternoon. But sooner or later, the authorities were going to get in. The NYPD took the usual approach for potential jumpers, getting to the floor above and rappelling down, kicking Mitchell safely back inside. Now, years after the arrest, it's easy to look back with all of the information and second guess how Mitchell got away with it for so long. But the truth is, at the time, Mitchell was incredibly convincing to a huge swath of people.

27:02Ian Mitchell:It was crazy. Like he just, he had it down pat. And there's only one little detail that Terrence picked up on as curious, even back then. And it's something that Mitchell never could have helped, not with any amount of research or training. Something that I always remember and now it keeps me on high alert, now that I study people and human characteristics, his hands were always so damn sweaty. It felt like you were shaking the hand like a sponge. Mitchell left a trail of damage in his wake. Even beyond the$700 ,000, plus what he stole, there's the incalculable psychological damage he inflicted on everyone who trusted him.

27:50Damage that can't be repaid.