S12, Chapter 1: The App on the Phone

0:00 It's getting dark outside. Tapes from the Dark Side. Contains descriptions of violence and sexuality. Listener discretion is advised. I don't even remember who is playing. I just remember the green and blue of the fan dual interface, the three hundred dollars number on the screen, and my thumb hovering over the button. But I honestly don't remember losing.

0:40 That's the part nobody tells you about gambling addiction. Nobody remembers their first loss. It slides off you like water off a dead man's back. It's nothing, it's a shrug. Your brain doesn't even bother filing it away. But your first win you remember that. The best way I can put it is it's kind of like the first time someone you trust puts their hand on your throat. You remember it not because it hurt, but because part of you liked it. Everyone remembers their first win. On January fifth, twenty twenty six, a man sat in a conference room in New Haven, Connecticut. Three of his closest colleagues were across the table. He had been their boss for two and a half years. One of them had a cell phone in his pocket, recording because he was afraid of what this man might do. When confronted, the man looked at them and said, and I'm quoting directly from a secretly recorded audio tape that is now part of a criminal case file quote.

1:49 I have a problem. I fixed my alcohol problem. I turned to gambling. I don't know why. It just got worse recently. That man was the chief of police of New Haven, Connecticut. His name was Carl Jacobson, and in the twelve months before that conversation, he had wagered four point four million dollars on sports betting apps on his phone. Four million, four hundred and sixty four thousand, eight hundred and eighty four dollars. That number will follow Carl Jacobson for the rest of his life.

2:35 I think everyone has a bit of a fascination of the dark side. I myself laws he loved the dark side as well. I think it's something that ever want to secretly longs for an months. To say that this news is a shock. As an understatement, it's a shock to me. It's a shock to the command staff. It's a shock to the men and women of the police department. It's a shock to the New Uban community.

3:24 It was late March twenty twenty six, and March Madness was in full swing. If you watch sports, if you even casually follow sports, you know what March looks like. Now. Every time out is a DraftKings ad. Every halftime is a FanDuel promo. To my international listeners who might be unfamiliar, March Madness is a national college basketball tournament, single elimination. The whole country watches, and my personal favorite thing about March Madness are the Cinderella stories, the under dogs, and I love a good underdog. I don't remember where I saw the first ad. It might have been scrolling on Instagram.

4:09 It might have actually been one of the timeouts on TV, but the offer caught my eye, not because it was necessarily flashy and featuring John Ham, but because, if you understand math at all, this looks like free money. That phrase free money might just be the most dangerous pair of words in the English language. It's the worm on the hook, the proverbial candy in the van. Ooh betting in space. New customers get up to three hundred dollars back in bonus bets every day for ten days. If your bets don't win. Here's how it works. You place a bet let's say three hundred dollars on a money line. If it wins, great, you keep your three hundred dollars steak and you keep the winnings. That's the best outcome. But if it loses, you don't automatically forfeit that three hundred dollar initial bet, because the next day FanDuel gives you what they call a bonus bet, three hundred dollars to bet on anything you want. If that bonus bet hits, then you keep the profit, not the three hundred dollars steak. So the backup plan is a worse deal, but it increases your odds of winning drastically. This promo ran for ten days, one three hundred dollars bet reset token per day. Now, I honestly had no intention of using it more than once.

5:33 I just wanted to make one March Madness game a little more interesting. If you bet and win, great, But if you bet and lose, you get a second chance. The absolute worst case scenario is I'm out three hundred dollars, not a small sum for a guy like me, But unlike the vast majority of gambling, the odds are actually in your favor, and at three forty in the morning on March twenty ninth, I placed that first bet, three hundred dollars on Tennessee over Michigan in the Elite eight plus two sixty. That's which call a long shot. It wouldn't be until about ten days later that I realized what actually happened In that moment. Something deep in my psyche was stirring. Later that day, Tennessee lost, but my three hundred dollars wasn't gone. Instead, I got the consolation prize.

6:31 The next day, a bet reset token kicked in, and now I had three hundred dollars in bonus money sitting in my fan duel account. I needed to pick another game. This time I picked another underdog, Yukon over Duke money line plus one eighty four. And what happened in that game matters not for the basketball, but for what it did to my brain. There is one spot remaining and one game left of the determined who goes to the final four. Duke was up big at halftime, forty four to twenty nine. Number one Seeds had been one hundred and thirty four and zero in tournament games where they led by fifteen points or more at half.

7:15 So a forty four to twenty nine, advantage for Duke and Yukon trying to climb out of this deep hold. Yukon's win probability at this point in the game was one point three percent, and then Yukon came back. Yukon down by as many as nineteen, they have a chance to cut it to two. The pressure is building now. Yukon erased a nineteen point deficit, the largest comeback ever against a number one seed in that situation, and with four tenths of a second left, a freshman named Brayln Mullins, who was nineteen years old, a literal teenager, launched a three pointer from thirty five feet away, still avous caravan.

8:03 Two seconds LUNs tosses it up. Why by y y Youn's not funningly. Utterly impossible over ukh still has the yard. Tragic Yukon seventy three, Duke seventy two. I won two hundred and fifty two dollars on a bonus bed on a game with a one point three percent win probability at halftime, And what ended up being important in that moment was not what happened on screen, but what happened inside me, Because something lit up that I hadn't felt in a long time, A warmth, a vibration in my rib cage that said, do that again, the way a dog here's a frequency you can't, the way a corpse flower knows when to bloom after ten years nothing. What happened to me in that moment has a clinical name.

9:07 It's called a dopamine response. More specifically along the Mesolympic pathway. It was more important than the money, more important than the apps, because that feeling that I got from watching Brayln Mullen's shot go in is the same feeling that grabbed the subject of our story. It's the first hit, and for some people, for people with brains like mine, it's the only hit the machine ever needs to give you. That exact feeling grabbed a man named Carl Jacobson. The difference is what we brought to the table when it hit us and what was waiting on the other side.

9:50 Carl Jacobsen was, by every external measure, exactly the kind of person you want running your police department. He was fifty five years old, a New England native. He had twenty seven years in law enforcement, nine years with the East Providence Police Department, starting in nineteen ninety eight, then the New Haven Police Department from two thousand and seven onward. Reclimbed from patrol officer to sergeant, to lieutenant to assistant chief. Along the way, he earned a US Attorney's Director Award in a National Association of Police Organization's Top Cop Award. These are not participation in trophies. These are recognitions given to officers who have done exceptional work. In May of twenty twenty two, after a nationwide search for a new police chief, New Haven Mayor Justin Ellicker chose Carl. He didn't pick someone from LA or Chicago or New York.

10:48 He picked the local guy, the one who'd been in the department for fifteen years. Carl was sworn in as chief on July sixth, twenty twenty two. So help me God, congratulations. When I started this journey of public safety, I had one goal in mind, and that was to make others feel safe. As chief as my responsibility to ensure that this department remains transparent and accountable and works for the community. He lived in Branford, Connecticut, with his wife, Dawn. They had two children, an older son named Carl and a daughter named Kelly. Hello, and welcome to Daylon New Haven and WNAHHTFM, new Haven's home for community radio. Today we have a man who is New Haven's new police chief, Carl Jacobson. Thanks so much for coming on the end of on WNHH.

11:38 Thanks for having me, Paul, It's good to be here. Like a chief, you had a pretty early on recommend firing some people who you personally liked. What was that, Like, how do you do that? Yeah? I mean since I've been chief, three people have been fired. There's a couple more that's been recommended to be fired on It's hard because you make connections with people and they work for you. But then when you have I have like people tell you the story and the stories like really over the top. And then and it was in this situation, it was just a matter of just telling the truth and and you're like what are you doing? You know, and you know, we're all human and we make mistakes. So I'm not looking to fire people, but I'm telling you the since the Randy Cox thing in the incident that you're talking about, you have to treat the community with respect and dignity. That's what it comes down to. If the officers did that in these different cases there would be a bit a different outcome. It almost sounds simple, Paul, give people a voice, treat them with dignity, neutrality and decision making. So you go to a call and even.

12:42 At the time of that interview, Carl Jacobson was already gambling. The warrant would later reveal that in the year following this conversation alone, he wagered more than four million dollars, and investigators believe it started long before that. But you can't hear it in his voe. There's no tremor, no desperation, no tells. That's the thing about this disease. It doesn't alter your behavior like drugs or alcohol. In fact, it makes you sound fine. It makes you sound exactly like yourself, right up until the moment the floor gives out. In December twenty twenty one, the University of New Haven published a Future Story about a father and daughter who shared a passion for criminal justice. Carl Jacobson and his daughter, Kelly, were attending the University of new Haven at the same time.

13:35 Carl was completing his Master of Science and criminal justice and Kelly was starting her undergrad degree, also in criminal justice. At the University's Henry C. Lee College of Criminal Justice and Forensic Sciences. They were in the same program the same time at the same school. Kelly told the university, and I'm quoting her directly. It's been great earning a degree while my dad is too. We're definitely able to bond over it, and sometimes we even get competitive about who has the better grades. Carl said, I am extremely proud of my daughter, who is a hard worker and a dedicated person.

14:17 Kelly wasn't just getting by. She was a field hockey player with a three point nine GPA. She was named a National Field Hockey Coaches Association Scholar of Distinction. She told the university that her father's dinner table stories about policing were what inspired her to major in criminal justice in the first place. By twenty twenty three, Kelly Jacobson wanted to become a New Haven police officer. She wanted to follow in her father's footsteps. Within three years of that university feature, Carl Jacobson will be arrested for stealing eighty five thousand dollars from the City of New Haven, including four thousand dollars from a fund that paid for children's basketball clinics and summer camps, written as checks to himself at Christmas time. But we're not there yet, not even close. Right now, in this moment, Carl Jacobson is a decorated police chief with a master's degree, a proud father, and a promising career. He is truly living the American dream.

15:26 A nice house Connecticut, his wife and kids. He goes to work every day and tries to make Newhaven safer, and somewhere, underneath all of it, something was already wrong. Something had been wrong for a long time, the kind of wrong that doesn't make noise. It just sits in the walls, like black mold, growing until one morning you peel back the wallpaper. We'll be back after a quick break. If you want to skip the ads and support the SHO show, you can do so at patreon dot com slash Tapes from the dark Side. We need to discuss something about Carl that might not seem relevant yet. Carl Jacobson had an alcohol problem. We know this because of what he said during that secretly recorded confrontation on January fifth, twenty twenty six, when his three assistant chiefs sat him down and asked him why the informant money was missing.

16:30 He told them, quote. I fixed my alcohol problem, he. Said, fixed past tense like a leaky pipe. You tighten like a house chore, you cross off a list. Now, before we dive into this, we should be careful. We don't know Carl Jacobson's full story. We don't know when he stopped drinking, if he saw a therapist, if he went to rehab, or if he just stopped. None of that info is in the arrest warrant, None of it is in any court filing. All we have is that one word fixed, and from personal experience, that word tells you a lot. Maybe not everything, but a lot. You see in recovery lingo, there's something that's beyond merely being sober.

17:21 It's called emotional sobriety. But I'm getting ahead of myself. For now, I just want you to file that word away. Connecticut legalized online sports betting in twenty twenty one, DraftKings fan Duel fanatics available on every smartphone in the state. For someone with Carl's history, this would turn out to be a very bad arrangement. Nathan Novemski, a Yale professor known for his behavioral economics and Consumer psychology research put. It like this, It's just like an alcoholic living in a liquor store or a bar.

18:03 Carl didn't have to drive to a casino, he didn't have to fly to Vegas. He didn't have to find a bookie or walk into an off track betting parlor. He just had to open his phone. When one of the assistant chiefs told Carl during their confrontation that he'd never actually seen Carl gamble, Carl picked up his cell phone, set her on the conference table, and said, quote, it's on the app four words. The whole catastrophe, the whole four point four million dollars, the stolen money, the children's fund, the career, the pension, the family. All of it lived inside of a rectangle glass and aluminum that fit in his pocket, that he carried everywhere, that slept on his nightstand, that no one ever thought to look at, because why would you It's just a phone. Let me tell you what happened inside my skull when Yukon hit the buzzer beater and I saw dollar signs appear on my screen.

19:07 There's a circuit in the brain called the mesolimbic dopamine pathway. It runs from a region called the ventral tegmental area deep in the brain stem, up to the nucleus accumbans, and then forward to the prefrontal cortex. This is the reward circuit. This is the system that evolved to make you feel good when you eat, you have sex, basic survival stuff. It's the system that says, whatever you just did, do it again. When you win a bet. This circuit fires. Dopamine floods the nucleus ocumban's euphoria, excitement, a sense of mastery.

19:48 Your brain tags the experience as important, It files it away. It builds an association. This app this action, this feeling, do it again. But here's the part that makes gambling addiction different from almost any other kind of reward. The dopamine response is strongest not when the reward is guaranteed, not when you know you're going to win. The dopamine fires most intensely during maximum uncertainty, when the odds are roughly fifty to fifty, when you genuinely don't know what's going to happen. Think of that Yukon game. A one point three percent win probability at halftime. Every possession in the second half is ratcheting up that uncertainty. As Yukon slowly comes back. By the final minute the game is nearly tied. Anything can happen. My brain was flooded with dopamine, not necessarily because of the money, but because of the not knowing.

20:53 Seventy to seventy ten seconds to go. The uncertainty itself is the drug. The money is just how it gets delivered. You just still have the more tragic and there's more. Researchers at Cambridge this was Luke Clark's team published in the journal Neuron in two thousand and nine, found that near miss outcomes activate the same reward circuitry as actual wins. If you bet on a team and they lose by one point on a last second play, your brain processes that almost the same way as it processes a win. Your brain lies to you, says you were close, you were right, the universe just got in the way. Instead of saying you lost. Stop, it says you almost won. Do that again. In pathological gamblers, this effect is even more extreme, and brain imaging studies show that problem gamblers actually have a stronger dopamine response to losses than healthy people do. They get more more pleasure from losing than a normal person gets from winning.

22:03 The disease of addiction has rewritten the source code. Loss is pleasure, pain is fuel. The worse it gets, the better it feels. I want to tell you something about myself that most of you don't know. On the show. I go by TZ, which stands for Tyler Zachary. That's my name. I go by Tyler in my personal life, but back in twenty twenty four, I started going by Tye. The reason being that was the year I came back back to my recovery, back to meetings, sponsor therapy, the whole thing, and I came back not from a relapse, but from something that might be arguably worse. For about four years, from twenty twenty to twenty twenty four, I was technically sober. I was making this podcast, which has been an incredible journey, and on the surface life was going okay. But underneath the surface it wasn't. I wasn't drinking, I wasn't using, but I wasn't in recovery. The pandemic had given me the perfect excuse to stop doing the internal emotional work that real recovery demands. The emotional sobriety.

23:22 It's the difference between just not using and actually being well. I didn't have it at the time. I was sober on paper, but falling apart underneath. The clinical research behind emotional sobriety might be the most overlooked aspect of this case, and I believe it might explain everything about what happened to Karl Jacobson. But for now, here's what you need to know about me. When I opened FanDuel and placed that first bed in March of twenty twenty six, my brain was not a normal brain responding to a normal stimulus. My brain had been shaped by u years of addictive behavior.

24:02 My brain has altered dopamine receptors and a prefrontal cortex that had been weakened by years of addiction and then four years without any emotional sobriety, a brain that was on a neurological level hungry. The science on this is not ambiguous. The DSM five, the so called bible of psychiatric diagnoses, though it's better at looking backward than forward, reclassified gambling disorder. In twenty thirteen they moved it out of the so called impulse control disorders and into substance related and addictive disorders, the same category as alcohol use disorder, the same category as opioid addiction. They did this because the research showed that gambling activates the same neural circuitry, shares the same genetic vulnerabilities, and produces the same patterns of tolerance with drawl and compulsive behavior as substance addiction.

25:01 The crossover data is staggering. Approximately thirty percent of people with a gambling disorder also have a substance use disorder. People with a substance use history develop gambling problems at four to five times the rate of the general population. The shared genetic vulnerability a variant called the DRD two TACK one A one allele, and it appears in both populations at elevated rates. Twin studies estimate that the heritability of gambling disorder is between fifty and sixty percent, which is comparable to alcohol addiction. What this means in plain language, if you've been addicted to one thing, your brain is pre wired to get addicted to another. Not because you're weak, not because you lack will power, but because the circuitry that was altered by the first addiction doesn't care what substance or behavior fills the void, it just wants the dopamine.

26:01 In gambling, especially mobile, sports betting, with its constant availability and its engineered uncertainty, delivers dopamine as efficiently as anything on earth. When I opened FanDuel for the first time and placed that bet, my brain wasn't starting from zero. It was a brain that had been primed by years of addiction, by a reward circuit that had been sitting in a dark room for a long time. And when Yukon hit that buzzer beater and two hundred and fifty two dollars appeared on my phone, the door didn't just open, it came off the hinges. The sports betting industry in the United States processed one hundred and forty nine billion dollars in wagers in twenty twenty four. In twenty seventeen, before the Supreme Court struck down the federal sports betting pan, the legal market was roughly four point nine billion, So in seven years, the industry grew by a factor of thirty.

27:05 DraftKings and FanDuel control approximately seventy percent of the American market. That promotion, I took the bet reset token that felt like free money DraftKings has reported that the average customer they acquire through those promotions has a lifetime value of approximately twenty five hundred dollars against an acquisition cost of three hundred and seventy one and they know that ninety five to ninety seven percent of customers lose in the long run. The promotions are not gifts, their bait, and once you become a so called heavy user, they don't just leave you alone. They assign you what's called a VIP host, a real person inside the company whose entire job is to keep you playing, to message you, to offer you personalized promotions, to learn your name, your habits, your patterns. Think of it as a friend who only calls when you're bleeding, who gets paid by the pint.

28:07 According to the arrest warrant, Carl Jacobsen had a customer relations person assigned to him by the sportsbooks. We don't know what they said to him. We don't know what promotions they offered, but we know the function they served. They were there to make sure Carl kept bleeding. We don't know if Carl won his very first bet. The warrant doesn't go into that kind of detail, but the data on his account tells us something. Across that first tracked year, he wagered four point four million and one back four point two. He was cycling money constantly, and the research on how gambling addiction develops is nearly universal on this point. Somewhere early on, there's a stretch of winning, a hot streak, a run where the mass seems to bend in your favor. Researchers call it the early winning phase.

29:06 Carl had a winning phase. I'm certain of it, because without it you don't make one thousand, three hundred and sixty six deposits. It's late March twenty twenty six. I'm sitting in my home phone in my hand, fandual app open a few hundred dollars richer, already entertaining the next bet, already noticing that another app, DraftKings is offering a sign up bonus. Bet three sixty five is offering three hundred and sixty five dollars on a ten dollars deposit, and bet mgm also has a promotion. I'm calculating how many apps I can sign up for, how much bonus money I could extract from the machine. But somewhere, something in the back of my mind is building a nest. Jacobson, sometime in twenty twenty four, is sitting somewhere in Branford, Connecticut, phone in his hand, DraftKings or fan Duel open, coming off his own first big win, his own dopamine flood, and inside him, something had already moved the furniture around and changed the locks. Two brains shaped by prior addiction suddenly fed. The only difference that mattered was invisible. It was internal. It had nothing to do with intelligence or character or moral fiber. It had to do with something

30:39 that happened or didn't happen in the years before we ever opened those apps. Carl said he fixed his alcohol problem for me, after four years of failing to work on myself. I had actually started the recovery process again. Carl, as far as we know, didn't have a sponsor therapist program. He didn't have someone he could call it too. In the morning, and the thing in the cross space started whispering, I did, and I almost didn't call him anyway. In the next episode, I'm going to tell you about what happened to me over the following ten days. How I downloaded nine sports betting apps, how I placed hundreds of bets, how I deposited thousands of dollars, and how I won, and how winning was the thing that nearly destroyed me.

31:36 I'm also going to tell you about what happened to Carl Jacobson over the following twelve months. How the arrest warrant said he made one thousand, three hundred and sixty six transfers from his checking account to gambling apps. How he started writing checks to himself from a fund meant to pay confidential informants while his daughter was home for the holidays. His daughter, Kelly, wanted to be a cop like her dad. She told the university that his dinner table stories are what inspired her. I wonder what the dinner table conversations are like now. The family hasn't spoken, and frankly, they don't owe us anything, but I think about her. I think about her a lot. I'm tz I've been your host, and this is Tapes from the Dark Side. If you or someone you know is struggling with gambling, the National Problem Gambling Helpline is available twenty four to seven. That's one eight hundred five two two four seven zero zero free confidential. You could hear the next episode in this series early ad free and in uncompressed pristine audio quality. Be that's on Patreon or Apple Podcasts.

33:03 Our newest Patreon members and you can join at patreon dot com. Slash Tapes from the Dark Side. At three dollars we have Jen Joy Bennett, Karris Becker, Jasmine and Gonzalez, Jonathan Greenway, Josh Lammy, Jessica Okugick, Andreas Sivillis. I'm probably saying that one wrong, Whitney Whimsical Pirate, Ellie yar Ralli, Britney Taunton, George E. Kinsey, Martin and Kelsey. And we have a four dollar member, Andrew Tallon five dollars members Danny Garaway, Kayla Barber or sorry, Kayla baber Russ, Di Capo Doctor, darce Anna Treante Couture, and at seven dollars we have Forlorn Flesh, and at nine dollars we have Elusive Sam Squach. Thank you to our associate producers Kayla Asthmus and Meg and also to our Seeker Tier members Lindsey Choy and Alison Barkley. You guys truly help the show keep going. Thank you for editing help from Chroi Turner.

34:35 Thank you to twenty six hundred, who allowed us to adapt one of his songs for our main theme. And thank you, of course to the incredible Augusta Trevororam who created original music that we used in today's episode. Please rate the show five stars on Apple or Spotify and send the show to a friend or post about it online anyway we can get the word out. If you want to get in touch with the show, you can do so at tapes from the dark Sidepod at gmail dot com or follow the show on Instagram at the dark Side Pod. Until next time, try to enjoy the daylight.

36:04 In nineteen seventy six, the first casino open outside of Vegas, and it was right here, about a half a mile from my home, across the boardwalk. The lines would wrap around the block. And when it first opened, I was twelve, so I was too young to really see anything beyond going in the lobby and just feeling the excitement. When I'm sixteen, we would slip in the casino. We'd play roulette. The lowest will be five dollars, so I put five on black and he put five on red, and one of us would win. But we'd drink for free until zero and double zero would come up, and so when you're sixteen fifteen bucks, there's a lot of money, twenty bucks whatever. I would lose every time I went.

36:58 It would take a while, and I get free beers, but then we'd leave and I'd have no money for the week until we could go back. I grew my own. Aversions to gambling. I saw it for what it was, a fool's bet, and I also had the good fortune of learning over twenty dollars a week and not the family mortgage.