Writing From The Inside: Gambling, Addiction, Prison, and Starting Over

Chris Swett
  • 5.0 (6)
  • Personal Journals
  • Updated Weekly

A former trial lawyer who negotiated over $100 million in settlements pleads guilty to wire fraud and money laundering tied to a gambling addiction that ran undetected for over two decades. Follow his journey through sentencing, prison, and ultimately reentry and redemption. Writing From The Inside is the honest account of how it happened and what it teaches about addiction, accountability, and what comes after for anyone carrying something they haven’t said out loud. writingfromtheinside.substack.com

Episodes

  1. 3d ago

    How to Tell Your Spouse

    There is a number in your head that your spouse does not know. You have rehearsed telling them in the car and at the kitchen table, but every time you found a reason to wait. I waited too. I hid a gambling addiction for years. Then, one day I was called into the office of the man who owned the law firm where my wife and I worked, and I knew what was coming before I sat down. After that meeting, I did not tell my wife the full truth. She learned about the invoices, the checks, and a bank account she never knew existed from someone else. This episode is what I wish someone had told me: how to get the whole truth on paper, what to say in the first minute, what never to say, and what the month after looks like. I also wrote a free guide to go with it. It has the full checklist, the script, what to hand over the same night, and where to get help for both of you. It is free for subscribers below. If someone you love is the one gambling, my first guide, The First Conversation, is written for you. You’ll find it in your welcome email after subscribing. If you need to talk to someone tonight, call or text the National Problem Gambling Helpline at 1-800-522-4700. Download the guide: How to Tell Your Spouse Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    How to Tell Your Spouse

  2. Oct 14

    Read the Fine Print

    FanDuel’s terms of use run almost 12,000 words. I read corporate documents for a living, and I never read this one. This week I put it on the witness stand and asked it five questions. One side of this relationship studies the other side every night. The other side never reads a page. New episode of Writing From The Inside Podcast is out now. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    Read the Fine Print

  3. Oct 7

    Relapse, Recovery, and What’s Coming Up

    Earlier this year I relapsed. I turned $100 into $6,000 and lost every dollar of it. Then, I did one thing I had never done before. This episode is about what I did different, what I learned about why I gambled to begin with, and what I’m building to replace it. It also has a CBS News update at the end. This one is for anyone who reaches for something when the stress builds and the noise gets loud enough. Not just gambling. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    Relapse, Recovery, and What’s Coming Up

  4. Sep 30

    From Federal Clerkship to Guilty Plea

    Right out of law school, I clerked for a federal judge in the District of South Carolina. One of the cases that moved through chambers that year was built on invoices for hauling that never happened, trucks that never moved, loads that were never transported, and paperwork manufactured to describe a reality that did not exist. The judge I worked for sentenced one of the defendants to sixty-five months. I was in the courtroom. I took notes on how the government had proved it, what the statute required, and what the sentence cost the woman it landed on. Years later, I created two companies, submitted invoices for legal work that was never performed, and used the proceeds to feed a gambling addiction. Four counts of wire fraud. Four counts of money laundering. Same federal district. This week's episode is my attempt at an honest answer to the obvious question, which is how a person who had watched it happen does it anyway. The answer is not that I forgot. I could have described that case in detail on any day between the afternoon of the sentencing and the morning I was called into the firm owner's office and found the general counsel already in the room. What failed was not the information. It was the connection between understanding a consequence and being reached by one. Knowledge of consequences is not protection from them, and the gap between the two is not a gap that education closes. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    From Federal Clerkship to Guilty Plea

  5. Sep 23

    Why Sports Betting Apps are Harder to Quit than Casinos

    This week's episode is about what the phone changed. A casino required my body to be somewhere else, and an absence is a thing a wife notices and can ask about in the morning. The phone required only my attention. It took that without leaving a trace. The concealment was not something I had to build because it came with the delivery mechanism. The part I most want people to take out of this episode is mechanical rather than moral: rebuild the friction the product removed and do not rely on the decision. The moment is where the impairment lives. Delete the app and close the account through self-exclusion. Put the App Store password in someone else's hands. Run Gamban or BetBlocker at the network level. Ask your bank to block gambling merchant codes. Give one person visibility into your statements. None of it depends on willpower, which is the part that already failed. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    Why Sports Betting Apps are Harder to Quit than Casinos

  6. Sep 16

    $100,000 Three Nights in a Row

    On a weeknight in late January, I picked Malcolm Brogdon at $5,400 because most of the field looked at that price and moved on. He finished with thirty-six points, seven rebounds, and nine assists. I won a hundred thousand dollars. I won again the next night. I won again the night after that. Three nights, three hundred thousand dollars. A month later the account was empty, and that is not a figure of speech. My wife never knew any of it happened. Not the wins, not the money, none of it. By the time she might have noticed a change in our life, it was already gone. This episode is about why that week felt like nothing. Not disappointing. Nothing, in the way a thermostat that has stopped registering temperature reads nothing. I also walk through what those afternoons actually looked like: four or five hours of spreadsheets, injury reports, pace and usage trends, matchup analysis, done with the same focus I brought to a set of medical records before a deposition. The skill was real. That is exactly what made it dangerous because it let me believe for years that I was closer to an investor than a gambler. The detail I had never said out loud before recording this is what my kids were doing that week. Homework, dinner, practice, a school project. I was in the room for some of it. I cannot describe a single hour of it back to you now. If you or someone you love has ever said that their functioning proves they do not have a problem, this one is for you. Sometimes the functioning is the problem. This week’s principle: pay attention to what happens in the moment right after you get the thing you wanted. Relief and rest mean you earned something. An immediate, automatic question about what comes next, arriving before you have felt anything at all, is a pattern that rarely resolves itself by winning more or experiencing more success. If this episode resonates with you, please consider sharing it and subscribing. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    $100,000 Three Nights in a Row

  7. Sep 9

    Loving Someone Who Is Addicted and Still Functioning

    Last week I gave you the conversation. This week is about what happens when it does not work, which is where most of you actually are. You said it. He denied it or he admitted a smaller version and told you it was handled. A week went by and nothing visible changed. Now he knows that you know, and the house feels different because of it. The question I get more than any other, phrased a dozen ways, is what to do if he will not stop and you are not going to leave. There is a real answer. Almost none of it is about stopping him. All of it is about limiting what he can take with him if he does not stop. Two things have to come off the table first. You cannot fix this by loving him harder or watching him more closely. My wife is a formidable person, and she could not do it, and the reason had nothing to do with any deficiency in her. I used her belief in me as evidence that things could not be as bad as they looked. Every increase in her vigilance produced an increase in my creativity. You also cannot wait for the bottom. For someone functioning at a high level, the room is enormous: savings, retirement, home equity, credit, borrowing, and then the places nobody wants to think about. Each one feels like a floor until it gives way. I fell through all of them, and the last one was a federal courtroom. What follows is the part you can do this week, alone, without another conversation and without his agreement. Separating finances at least partly. Freezing your credit at all three bureaus and reading the report. Protecting any account you are responsible for as a trustee, signatory, or treasurer because that is where a private problem becomes a criminal one. Keeping a record he cannot see. Talking to your own lawyer one hour before you think you need one. Taking the technical fixes if he offers them and not mistaking them for the end of the problem. I also cover the difference between an ultimatum and a boundary, which is the most practical distinction in this whole subject, what to say to your children and what never to ask of them, and the first forty-eight hours if something breaks. Resources: National Problem Gambling Helpline, 1-800-522-4700. If you are worried about his life, that takes priority over everything else in this episode. In the United States, call or text 988. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    Loving Someone Who Is Addicted and Still Functioning

  8. Sep 2

    How to Actually Have the Conversation with an Addict

    The first four episodes of this show were about me. What I lost, what I did to my wife, what the numbers on my account statement looked like at the end of two years. This one turns around and faces the other direction. This episode is not for the person who is gambling. It is for the wife who has started checking the bank app before she gets out of bed. The parents who noticed their son asked for money twice in one month and cannot decide whether that means anything. The law partner who saw something on a screen in a conference room and told himself he did not really see it. If that is you, you have been trying to figure out how to say something for a while now. You have rehearsed it in the car. You have started it four times and abandoned it. You are afraid that if you say it wrong you will lose your only chance, and afraid that if you say it right, everything you are worried about will turn out to be true. I can talk about this because I was on the other side of that conversation more than once. I know what worked on me and what did not. What I cover Why the standard advice fails. Most of what you will find online was written for an addiction that leaves evidence. Missed work, bottles in the trash, a crisis that has already announced itself. None of that language fits the man who got a promotion last year, coaches your kid’s team, and made the mortgage payment on time. The functioning is not evidence against the problem. In a lot of cases the functioning is the engine of it. I was at my most productive during the worst of it, and every one of those days worked as proof. Not proof to anyone else. Proof to me. Three things to do before you say a word. Write down what you have observed instead of what you have concluded. Decide in one sentence what you actually want out of this. Pick the time, because the time matters more than the words. Five things not to do. Including the one most people lead with: asking a question you already know the answer to. When I was asked directly how much I had lost, I gave a number that was not close. I did not decide to lie. The smaller number was the only number I could say out loud and still be the person I was pretending to be. The shape of the actual conversation. One observation, the true thing about yourself, one open question, and then the hardest instruction in the episode, which is to stop talking. What to expect after, including the three situations where you should not be handling this alone. The honest answer You are probably wondering whether any of this would have worked on me. The first conversation did not work. Neither did the second. What they did was put a fact in the room. After the first one I could no longer tell myself that nobody had noticed, and every single thing I did after that required an act of will it had not required before. I gambled for years more. It cost me more effort to do it and continue to hide it. That is not a failure. You are not going to talk anyone out of this in one afternoon. What you can do is make it more expensive to continue and make it clear where the door is when he finally looks for it. The people who get out almost always tell you there was someone standing there the whole time. If you need help right now The National Problem Gambling Helpline is 1-800-522-4700. It is free, it runs all day and all night, and it is for family members, not just for gamblers. You are allowed to call before you are certain. Most people who call are not certain. If he has said anything about not being around, or about everyone being better off without him, do not manage this privately. Gambling addiction carries one of the highest known suicide rates. Next week Part two. What you do when the conversation is over, he stills denies it, and you have to figure out how to protect your family from someone you are not willing to leave. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    How to Actually Have the Conversation with an Addict

  9. Aug 25

    What FanDuel Knew about Me- Sports Betting Addiction and the Data

    Ninety-five percent of the losses in the sports betting industry come from five percent of the people betting. The apps know exactly who that five percent is, in real time, the same way a casino used to need hours to spot a player in trouble. I was in that five percent for years, and once I crossed a certain threshold, I got a personal host, tickets to events, and offers that arrived like clockwork right after a deposit failed. I self-excluded from the platform after everything collapsed. Within the last thirty days, I still received promotional emails trying to get me back on. This episode is about what that industry actually knew, what it built to keep me playing, and how deeply it’s now woven into the leagues and broadcasts most of us watch without a second thought. Most people in that five percent will not say it out loud. The people around them notice first. Running this one a day early. New episode every Wednesday. Subscribe and it comes to you. If someone you know has a VIP host, send them this one. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    What FanDuel Knew about Me- Sports Betting Addiction and the Data

  10. Aug 19

    What I Did to My Wife's Name- When Wire Fraud Reaches Your Family

    I put my wife's name on a company that was committing fraud, and she had no idea it existed. She never saw an invoice, never touched a check, never signed a single document. Her name was on the formation paperwork because I put it there, on purpose, so the whole scheme would have a layer of cover I needed and she never agreed to carry. Eventually, that company was investigated by the FBI. So was she, for over a year, for something she had no knowledge of and no part in. This episode is about that specific decision, why I made it, and what it actually cost her. It's the hardest one I've recorded so far, and I think it's the one that says the most about what this show is actually going to be honest about. Next week’s episode: What FanDuel Knew About Me- Sports Betting Addiction and the Data they Keep. I’m writing this the whole way through. Before I go in, while I’m in, and after. New episode every Wednesday. Subscribe below and it comes to you. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    What I Did to My Wife's Name- When Wire Fraud Reaches Your Family

  11. Aug 11

    Writing From The Inside- The Podcast

    I spent over a decade as a trial lawyer, negotiating settlements worth more than a hundred million dollars for people who'd been hurt by companies that should have known better. I also gambled away everything I built, wagering over eleven million dollars over two years, and eventually committed federal crimes to keep it funded. I pleaded guilty to wire fraud and money laundering, and by the time you're hearing some of these episodes, I'll likely already be in federal prison. This show is my honest account of how that happened, told one specific story at a time, without skipping the parts that make me look bad. Some episodes are my story. Others take something I learned the hard way and turn it into something you can actually use whether or not gambling has ever touched your life. If you're carrying something you haven't said out loud yet, or you love someone who might be, I think you'll find something here worth your time. Get full access to Chris Swett’s Writing from the Inside at writingfromtheinside.substack.com/subscribe

    Writing From The Inside- The Podcast
  • 11 Episodes

Ratings & Reviews

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About

A former trial lawyer who negotiated over $100 million in settlements pleads guilty to wire fraud and money laundering tied to a gambling addiction that ran undetected for over two decades. Follow his journey through sentencing, prison, and ultimately reentry and redemption. Writing From The Inside is the honest account of how it happened and what it teaches about addiction, accountability, and what comes after for anyone carrying something they haven’t said out loud. writingfromtheinside.substack.com

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