Speaker 1: It's getting dark outside.
Speaker 2: Tapes from the Dark Side contains descriptions of violence and sexuality.
Speaker 3: Listener discretion is advised.
Speaker 1: Almost nobody writes checks anymore. It would probably take you
Speaker 1: a minute to find your checkbook right now. I know
Speaker 1: it would for me. There's a whole generation that has
Speaker 1: never filled one out, never will, and would have to
Speaker 1: be taught. The date here, the amount there, sign here.
Speaker 1: And even though it's essentially an antique, it's an antique
Speaker 1: with function. On every check, there's one place, the lower
Speaker 1: left corner, where you write what the money was for.
Speaker 1: It doesn't get filled out every time. The bank doesn't
Speaker 1: even read that line. It changes nothing about where the
Speaker 1: money goes. It's there mostly for the person writing the
Speaker 1: check or the person receiving it. It's called the memo line.
Speaker 1: Two checks were drawn on an account belonging to the
Speaker 1: Police Activity League of New Haven, PAL. It's a non-profit
Speaker 1: the police department runs for kids. funded by donations, a
Speaker 1: few grants, and small automatic deductions out of the paychecks
Speaker 1: of New Haven's own police officers. Together, the two checks
Speaker 1: came out to $ 4, 000. The memo line on the first check,
Speaker 1: toy giveaway. The memo line on the second check, toy drive.
Speaker 1: Both were deposited into the personal checking account of Carl Jacobson.
Speaker 1: I know about these checks because they're described in a
Speaker 1: 10-page document, an arrest warrant affidavit written by a Connecticut
Speaker 1: State Police Lieutenant in February of 2026. In Connecticut, that
Speaker 1: document goes public almost as fast as the cuffs go on.
Speaker 1: Most of what you're about to hear tonight comes out
Speaker 1: of those 10 pages. 10 pages for a year like his,
Speaker 1: it's not a lot of paper. The apps kept a
Speaker 1: better record.
Speaker 2: I think everyone has a bit of a fascination with
Speaker 2: the dark side. Is there anything you can say about
Speaker 2: trying to tell people why you did what you did?
Speaker 4: It was something that I got caught up in with
Speaker 4: the ease of having it on an app.
Speaker 1: When the state of Connecticut wants to know what you've
Speaker 1: been up to on DraftKings, it doesn't ask you. It
Speaker 1: goes directly to DraftKings. Investigators served search warrants on the
Speaker 1: gaming platforms, and the platforms handed over all of Carl's records.
Speaker 1: What Came Back covers one year, almost to the day,
Speaker 1: January 1st, 2025 through January.
Speaker 2: 5th, 2026.
Speaker 1: The records stop on January 5th. The meeting in Carl
Speaker 1: Jacobson's office, the one where three assistant chiefs sat him down,
Speaker 1: that was also January 5th. Here's what the year looked
Speaker 1: like for Carl. $ 4, 464, 884. 26. That's the wagered number. And on
Speaker 1: its own, it's a lie of size. Wagered is not lost.
Speaker 1: Wagered is churn. The same dollars go through the door,
Speaker 1: come back out, and then go in again. So here's
Speaker 1: the column that matters.
Speaker 5: Net.
Speaker 1: It's not $ 4 million, but it's not a small number either. $ 214, 365.
Speaker 1: And 74 cents. The machine doesn't round. Carl's salary as
Speaker 1: police chief was around $ 180, 000 a year. Put those side
Speaker 1: by side, he lost more than the job paid. Every
Speaker 1: shift of the last year as chief, every lineup, press conference,
Speaker 1: every hour of overtime, the app took. There's another number.
Speaker 1: Perhaps one that tells an even more insidious story than
Speaker 1: the six and seven digit numbers.
Speaker 3: 1,366.
Speaker 1: That's how many times Carl's personal checking account pushed money
Speaker 1: into one of those two apps in that one year.
Speaker 1: If you do the division, that comes out to three,
Speaker 1: sometimes four transfers a day, every day for a year.
Speaker 1: There's only one kind of person who sits down to
Speaker 1: move money three or four times a day for a
Speaker 1: habit they can't afford. I have experience with the type
Speaker 1: of financial documents we've been discussing in regards to Carl's history.
Speaker 1: In April, I downloaded my own bank activity from the
Speaker 1: 10 days it exported as a spreadsheet. In every line
Speaker 1: where my checking account or my card touched a sportsbook
Speaker 1: is sitting there. Written the way the machine writes. Transfer.
Speaker 5: MGM.
Speaker 1: Asterix. New Jersey. Card.
Speaker 2: 7356.
Speaker 1: Negative $ 660. 49. No emotion. Clinical. A reference number on the
Speaker 1: next line. 28 characters long. 40 lines in 10 days.
Speaker 1: 9 different companies. Carl Jacobson averaged 3 to 4. But
Speaker 1: I hit 10 transfers in a single day quite easily.
Speaker 1: I was outpacing Carl straight out the gate. There's a
Speaker 1: thing that gamblers do. And I did it too. We
Speaker 1: talk about the wins. The scratcher that hit. The lotto
Speaker 1: number that came in. The long shot parlay. My Yukon
Speaker 1: buzzer beater. I told you that one with my whole chest.
Speaker 1: And part of me wants to tell it again. The
Speaker 1: story of the wins. Sometimes you'll hear of people's losses, briefly,
Speaker 1: but they don't like to talk about those as much.
Speaker 1: Sometimes they'll acknowledge them, sometimes they won't. The number no
Speaker 1: active gambler likes to talk about, though, is their net.
Speaker 1: The number for their career, or even just the last year.
Speaker 1: Every bet stacked against every payout. That number never comes
Speaker 1: up at the bar, and there's a reason why. Now,
Speaker 1: the net isn't hidden from you if you use a
Speaker 1: sports betting app. It's there. There's a screen tucked away
Speaker 1: behind a few menus that shows you exactly where you stand.
Speaker 1: It's not the most convenient to find, but it's not
Speaker 1: that hard either. It's just down a hallway that you
Speaker 1: have to decide that you want to walk down. And
Speaker 1: after a stretch of losing, that hallway starts to look
Speaker 1: very long. The net is the number you avoid. When
Speaker 1: you look at Carl's page, one, 4.25 million. Looks like
Speaker 1: a guy who mostly wins. And I'm quite sure Carl
Speaker 1: Jacobson had a few of his own Yukon buzzer beater
Speaker 1: stories to tell. The most complete record of Carl Jacobson's
Speaker 1: last year as chief of police does not exist at
Speaker 1: a headquarters on Union Avenue. It's not in a city file.
Speaker 1: It sits on servers owned by two betting companies, accurate
Speaker 1: to the second, accurate to the cent. When we run
Speaker 1: the math, we have an immediate and obvious problem. Money
Speaker 1: was leaving Carl's checking account faster than the job could
Speaker 1: put it there. The arithmetic has a hole, and that
Speaker 1: money had to come from somewhere. Since July of 2019,
Speaker 1: before he was ever chief, Carl Jacobson handled the money
Speaker 1: New Haven uses to pay CI's confidential informants. It ran
Speaker 1: through the Narcotic Enforcement Program, about $ 5, 000 a month, and
Speaker 1: per the sworn statement in that warrant, it ran through
Speaker 1: exactly one man. He received it, he dispensed it, he
Speaker 1: kept the log. When I got to this part of
Speaker 1: the story, I got curious. I had heard of a
Speaker 1: confidential informant, and I knew they got paid, but how
Speaker 1: the hell does that actually play out in real life? Well,
Speaker 1: let's say, for example, a CI agrees to wear a
Speaker 1: wire during a narcotics bust. The police come in, make
Speaker 1: their arrests. It's not really glamorous, but it's not a
Speaker 1: metaphor either. The government quietly paying its citizens to tell
Speaker 1: on each other. It's a real part of how these
Speaker 1: cases get made. So the fund custodian writes a check,
Speaker 1: Somebody cashes it, the actual cash goes into an envelope,
Speaker 1: and the officer hands it to the informant, who signs
Speaker 1: a receipt for the exact amount. By the book, a
Speaker 1: second officer is supposed to witness the handoff. Cash in,
Speaker 1: signature back. New Haven system had one man holding all
Speaker 1: of it he wrote the request he cashed the check
Speaker 1: he carried the cash and he kept the only ledger
Speaker 1: the second officer the second signature did not exist So
Speaker 1: we get to December 23rd of 2025, two days before Christmas.
Speaker 1: A sergeant in the intelligence unit picks up the phone.
Speaker 1: What he said right after this quick break. If you
Speaker 1: want to skip the ads and support the podcast, you
Speaker 1: can do so at patreon.com slash tapes from the dark side.
Speaker 1: The sergeant's name is Francisco Sanchez. He works in the
Speaker 1: intelligence unit, and the call he makes, two days before Christmas,
Speaker 1: is to an assistant chief, David Zanelli. He tells Zanelli
Speaker 1: something's wrong with the chief. Not the gambling. Nobody at
Speaker 1: the department knows about the gambling yet. On December 23rd,
Speaker 1: not a single person in New Haven had any idea
Speaker 1: their chief had been quietly moving hundreds of thousands of
Speaker 1: dollars out of his own account into two apps for
Speaker 1: most of the year. What Sanchez had was smaller, but
Speaker 1: it was significant. The informants didn't get paid. November and
Speaker 1: then December. Two months, the money that's supposed to reach
Speaker 1: the people taking real-life risks to talk to police just
Speaker 1: never showed. And the only man who can say why
Speaker 1: is Carl Jacobson. Here's how the story goes. Chief Jacobson
Speaker 1: gave his lieutenant $ 2, 000 to pay informants. That lieutenant was
Speaker 1: Derek Werner. And then Carl walked into Werner's office and
Speaker 1: took half of it back, $ 1, 000 out of the envelope.
Speaker 1: And where the money was, he left a note, quote.
Speaker 5: Took $ 1, 000, $ 12. 2325, Chief Jacobson.
Speaker 1: The chief of police wrote an IOU and a cash
Speaker 1: fund for confidential informants and signed it with his rank.
Speaker 1: But those informants still needed paying. People had done the
Speaker 1: work and they were owed money. So Sergeant Sanchez paid
Speaker 1: them out of his own pocket. One man at the
Speaker 1: top quietly took and one man below him quietly covered.
Speaker 1: In that same stretch of December, The chief asks Werner
Speaker 1: for one more thing, a personal loan, $ 500. You already
Speaker 1: have the other number, $ 214, 000. And here, two days before Christmas,
Speaker 1: the same man is asking a lieutenant who reports to
Speaker 1: him to float him $ 500. I know what that feels
Speaker 1: like from the inside, but I can't describe it in words.
Speaker 1: It's something I hope you will never have to feel
Speaker 1: for yourself. The men who suspected something was wrong didn't
Speaker 1: walk in and confront Carl unafraid. Per the warrant, they
Speaker 1: thought if they flagged the chief, the chief would come
Speaker 1: for them, move them off their post, kill their overtime.
Speaker 1: A lieutenant afraid of what telling the truth would cost him,
Speaker 1: a sergeant covering a debt out of his own paycheck,
Speaker 1: and a handwritten IOU. Now let's go back and look
Speaker 1: at the date on that note again. December 23, 2025.
Speaker 1: Those two checks I read you at the top of
Speaker 1: this episode, the ones from the kids' accounts, made out
Speaker 1: to Carl Jacobson himself, toy giveaway, toy drive, they're dated
Speaker 1: December 23, 2025. One for $ 1, 000, one for $ 3, 000. The
Speaker 1: administrative assistant who prepared them is named Tina Tremaglio. She
Speaker 1: told investigators it struck her as odd A toy drive
Speaker 1: this close to Christmas and the checks written out to
Speaker 1: the chief himself? This kind of systematic abuse of power
Speaker 1: doesn't happen by accident. It takes a while to take shape.
Speaker 1: How did none of the assistant chiefs think it was
Speaker 1: odd that Carl Jacobson had sole access to the CI fund?
Speaker 1: When they asked Zanelli that, he didn't have an answer.
Speaker 1: He said they asked Carl repeatedly for access to the fund.
Speaker 1: Carl told them that he couldn't let them have access
Speaker 1: to it because he wanted to protect them from liability.
Speaker 1: Sounds like the kind of thing a good boss says.
Speaker 1: Zanelli was coming up on his first year running investigations
Speaker 1: and the job comes with an annual audit. He was
Speaker 1: prepping for it. On January 3rd, a supervisor in management
Speaker 1: services pulls the records for Zanelli In November, Carl Jacobson
Speaker 1: had cashed two checks from the informant fund, $ 5, 000 each.
Speaker 1: In December, two more, $ 20, 000 in six days. January 5th,
Speaker 1: three assistant chiefs confront Carl Jacobson, a phone quietly recording
Speaker 1: on the conference table because they were afraid of how
Speaker 1: it was going to go. From the affidavit, chief is
Speaker 1: asked approximately how much money is missing, and he responds, $ 10, 000.
Speaker 5: Quote, I have you guys in a bad situation and
Speaker 5: I just ask that you allow me to replace the
Speaker 5: money and I'll retire and we fix the books and
Speaker 5: pass it over to one of you.
Speaker 1: Assistant Chief Etienne responds that Jacobson is asking them to
Speaker 1: double down on a wrong. Jacobson responds, No, I understand.
Speaker 5: And then later says, I'm just asking for an opportunity
Speaker 5: to save myself. Because here, I mean, there's a potential
Speaker 5: to go to jail, right? Because I misused government funds.
Speaker 5: I won't get a pension. I'll go to jail.
Speaker 1: Assistant Chief says, I'm not the judge or jury. Jacobson responds,
Speaker 1: I know.
Speaker 5: I'm just saying it's not that I'm a bad person.
Speaker 5: I have a problem. I fixed my alcohol problem. I
Speaker 5: turned to gambling. I don't know why it just got
Speaker 5: worse recently.
Speaker 1: A.C. Zanelli tells Chief, I've never seen you gamble. Chief
Speaker 1: Jacobson responds, It's.
Speaker 5: On the app. $ 10, 000.
Speaker 1: That's the number Carl confessed to. And the officers in
Speaker 1: front of him knew it was a lie the moment
Speaker 1: it left his lips. Remember two days earlier, a supervisor
Speaker 1: in management services had pulled the checks for Zanelli, two
Speaker 1: in November, in December, 5,000 apiece. The men sitting across
Speaker 1: from Carl knew the number was at least twice what
Speaker 1: he confessed to, but 20,000 wasn't the real number either.
Speaker 1: The state was about to put a forensic accountant on
Speaker 1: the case. We're not done counting. The next week went
Speaker 1: by in a flash. By the end of that day
Speaker 1: when the confrontation took place, Monday, January 5th, Carl was
Speaker 1: no longer chief of police. but he hadn't been fired.
Speaker 1: You see, immediately after that meeting, Carl retired. The paperwork
Speaker 1: was sent in the same exact day, effective immediately, pension secured,
Speaker 1: at least for now. Carl filed for retirement before anyone
Speaker 1: had a chance to react. He never went back to
Speaker 1: that office. Cinelli reported it up the chain and had
Speaker 1: the locks changed. By Friday, Carl's lawyer called the state's
Speaker 1: attorney and to let them know his client was invoking
Speaker 1: the Fifth and would not be talking to police. So
Speaker 1: Carl didn't run. He didn't try to destroy any evidence
Speaker 1: as far as the record shows. What he did was
Speaker 1: faster and more efficient. He followed procedure. He exploited the
Speaker 1: system that he had been a part of for his
Speaker 1: whole career. Retirement filed, the Fifth invoked before an interview
Speaker 1: could even be scheduled again. Every move by the book.
Speaker 1: 27 years of knowing exactly how the machine processes a
Speaker 1: man in trouble. On January 23rd, state police seized the
Speaker 1: bank records and a forensic accountant from the FBI sat
Speaker 1: down with two stacks of paper. Carl Jacobson's personal checking
Speaker 1: account on one side, the narcotic enforcement program on the other.
Speaker 1: And they started to compare.
Speaker 6: 2025.
Speaker 1: 14 checks, $ 5, 000 each, $ 70, 000 total cashed. 23,000 of it
Speaker 1: shows up in expenditure reports, money that got where it
Speaker 1: was supposed to go, documented, accounted for. The other 47,000 isn't.
Speaker 6: Then they went back a year to 2024, another 34,000 cashed,
Speaker 6: unaccounted for. $ 81, 500 out of the fund that pays people
Speaker 6: to talk to the police, plus the $ 4, 000 that was
Speaker 6: supposed to go to the kids.
Speaker 3: $ 85, 500.
Speaker 2: Gone.
Speaker 1: Carl admitted to $ 10, 000. Now the interesting thing is $ 14, 000
Speaker 1: of it, they could follow the whole way out of
Speaker 1: the fund into the checking account. Carl admitted to 10. Now,
Speaker 1: the interesting thing is 14,000 of it, they could follow
Speaker 1: the whole way out of the fund into the checking account,
Speaker 1: out of the checking account into DraftKings and FanDuel, traced precisely.
Speaker 1: Two of the informant checks turned up as photocopies when
Speaker 1: the state seized Carl's bank records, 5,000 each deposited into
Speaker 1: his personal account. Both of them cashed the same day
Speaker 1: they were written No gap, not even a night to
Speaker 1: sleep on it. There's a line from Werner in the affidavit.
Speaker 1: Carl cashed $ 5, 000 a month. He handed Werner usually two,
Speaker 1: never more. Werner told investigators he didn't know what happened
Speaker 1: to the rest. For six years, nobody knew what happened
Speaker 1: to the rest because there was nobody whose job it
Speaker 1: was to know except Carl Jacobson. But the kids' fund
Speaker 1: hurts more than the informant money. at least for me,
Speaker 1: and it seems like it lingered for Carl as well.
Speaker 1: The Connecticut State Police Eastern District Major Crime Unit obtained
Speaker 1: a signed and sworn statement. From the executive director of
Speaker 1: the New Haven Police Activity League program, we glossed over it.
Speaker 1: So I just want to quickly describe what the PAL
Speaker 1: actually is. It's a youth program that directly connects law
Speaker 1: enforcement officers with children and teens, which you might call
Speaker 1: troubled youth programs. A free event they actually hold in
Speaker 1: New Haven. It's called Homework and Hangout, 5 to 7 p.m.
Speaker 1: on Tuesdays and Thursdays. You can drop your kid off.
Speaker 1: They'll be supervised. They can read books, play board games,
Speaker 1: or just do their homework. It's a real program with
Speaker 1: real tangible benefits for the community. On January 29th, 2026,
Speaker 1: at 1248 p.m., the executive director of the PAL announced
Speaker 1: received a call from an unfamiliar phone number. He returned
Speaker 1: that call, and when the person answered, they said, Hey,
Speaker 1: it's Carl. From the affidavit.
Speaker 5: Jacobson stated that he was sorry for letting the police
Speaker 5: department down, letting him down, and letting the PAL down.
Speaker 5: Jacobson also said that he had heard that people were
Speaker 5: claiming he had taken money from PAL, and he wanted
Speaker 5: him to know this was not true. Jacobson explained that
Speaker 5: he had cashed two checks to support a woman's toy drive.
Speaker 5: But after the events at the police department, the woman
Speaker 5: wanted nothing to do with him or his money. Jacobson
Speaker 5: told the director that he deposited the funds back into
Speaker 5: the PAL account. The information that Jacobson told him is
Speaker 5: consistent with the $ 4, 000 cash deposit into the New Haven
Speaker 5: Police Activity League banking account on January 16th, 2026.
Speaker 1: Could have been a simple slip of the tongue. I've
Speaker 1: never heard of a woman's toy drive. We've all heard
Speaker 1: of a children's toy drive. But I think we all
Speaker 1: know the most likely reason that Carl got his words
Speaker 1: mixed up. Because there was no toy drive. The sportsbooks cooperated.
Speaker 1: When Connecticut State Police came with warrants, DraftKings and FanDuel
Speaker 1: didn't flinch. They opened the file and handed over a
Speaker 1: year of Carl Jacobson's betting activity. Every wager, every deposit,
Speaker 1: every dollar to the cent. They knew precisely who Carl was.
Speaker 1: He was one of their best customers. Back in episode one,
Speaker 1: I said the warrant showed Carl had a customer relations
Speaker 1: person assigned to him. That may have been incorrect. At
Speaker 1: least the warrant doesn't say that. Where I actually got
Speaker 1: that from is a man named Jonathan Cohen, who wrote
Speaker 1: a book about the American sports betting industry and who
Speaker 1: sat down with a New Haven reporter days after Carl
Speaker 1: Jacobson's arrest and read the same 10 pages that we've
Speaker 1: been reading through. He described how these companies work. They
Speaker 1: find the big fish. They put a line on them.
Speaker 1: And the reporter noted in the piece that Cohen was
Speaker 1: not talking about Carl specifically and He was saying that
Speaker 1: Carl's story fits a pattern. So here's what we actually
Speaker 1: know and can prove. I can tell you what this
Speaker 1: industry does to men who bet the way Carl Jacobson bets.
Speaker 1: That is documented. And it's in job listings, earning reports,
Speaker 1: and regulatory filings. I cannot confirm that this was done
Speaker 1: specifically to Carl. At least not yet. We've talked about
Speaker 1: the gambling ads. They sell you a stadium where everybody's
Speaker 1: got 20 bucks on the game. Everybody's yelling at the screen.
Speaker 1: Everybody's having a night. That's the picture. Millions of people
Speaker 1: having a little fun and some of them winning big.
Speaker 1: That is not the business. Everyone in the stadium is losing.
Speaker 1: You know this from episode two. The price is baked
Speaker 1: into every line on the board and the math doesn't
Speaker 1: take a night off. Sure, you might win a bet
Speaker 1: or two in the short term. You might have a
Speaker 1: 10-day winning streak. But over the long haul, you will
Speaker 1: never come out ahead. The longer you bet, the more
Speaker 1: you wager, the more it is guaranteed you will lose money.
Speaker 1: This is not like a game of battleship where each
Speaker 1: bet gets you closer to a hit. Nobody in the
Speaker 1: stadium is beating the machine in the The only question
Speaker 1: is how fast you lose and how much. And if
Speaker 1: you are one of those ones who is cursed with
Speaker 1: a big win early and you happen to have a
Speaker 1: genetic predisposition to betting addiction, then you might very well
Speaker 1: have hit the jackpot, but in a way you might
Speaker 1: not understand yet. The sportsbook PointsBet, in its own filing,
Speaker 1: showed that VIP customers were half of 1% of its users. 0.5%
Speaker 1: brought in more than 70% of revenue. Fill your stadium
Speaker 1: with 20,000 people, and the business is 100%. But let
Speaker 1: me say again very clearly, the other 19,900 are not
Speaker 1: winning anything. They're losing small, slowly, on schedule, by design.
Speaker 1: Losing at a rate that feels like entertainment. They are
Speaker 1: the scenery, and the scenery is what keeps the 100%
Speaker 1: from feeling like what they really are. Marks. So there's
Speaker 1: a job, a real job, posted publicly. You can probably
Speaker 1: find listings for it tonight if you go online. VIP
Speaker 1: account manager at FanDuel. Salary, $ 60, 000 to $ 70, 000 a year.
Speaker 1: Job description, manage the portfolios of high-value clients, build relationships,
Speaker 1: encourage loyalty, keep a documented profile on them. host them
Speaker 1: at events. And down in the qualifications, it says you
Speaker 1: should be able to, quote, identify customer trigger points. Run
Speaker 1: that through any other addiction, a liquor company, hiring customer
Speaker 1: relations people who can manage a portfolio of alcoholics. Sounds
Speaker 1: a little bit like a bartender, but it's much more
Speaker 1: insidious than that. Because a bartender doesn't text you when
Speaker 1: you haven't shown up for a drink. In 2023, a
Speaker 1: man named Amit Patel pled guilty to stealing $ 22 million
Speaker 1: from the Jacksonville Jaguars NFL football team. He was their
Speaker 1: manager of financial planning, 31 years old. And the way
Speaker 1: he did it is going to sound familiar. The Jags
Speaker 1: had given him control of the team's virtual credit card.
Speaker 1: One man, four years, and nobody over his shoulder. $ 22, 221, 000. $ 454. 40,
Speaker 1: $ 20 million of that went to FanDuel. Patel is serving
Speaker 1: six and a half years in federal prison, and in 2024,
Speaker 1: he sued FanDuel for $ 250 million. The lawsuit is where
Speaker 1: the following details come from. They're not facts, they're Patel's allegations.
Speaker 1: They have not been proven, and FanDuel has predictably declined
Speaker 1: to comment. Patel says FanDuel made him a VIP, says
Speaker 1: they gave him $ 1. 1 million in credits. He says they
Speaker 1: flew him to the Super Bowl, the Masters twice, the
Speaker 1: college football playoff championship, and Formula One in Miami. And
Speaker 1: he says he had a host, an actual person with
Speaker 1: a name, Brett Krause. Patel alleges that Krause contacted him
Speaker 1: as many as 100 times a day, starting early in
Speaker 1: the morning, running late into the night for two years.
Speaker 1: On days Patel didn't gamble, he says Krause called him
Speaker 1: to ask him why. We don't really need to hear
Speaker 1: anything more than that, but the suit goes on. It
Speaker 1: also claims Krause acknowledged more than once that the two
Speaker 1: of them were breaking anti-money laundering rules, that they moved
Speaker 1: some of their texts onto Krause's personal phone so compliance
Speaker 1: wouldn't see them, and that he coached Patel on what
Speaker 1: to say when they were communicating on the company phone. But,
Speaker 1: as a renowned doctor once said, I don't care how
Speaker 1: flat you make a pancake, there's always two sides. Krause's
Speaker 1: attorney called Patel a convicted fraudster. She said he lied
Speaker 1: to Krause about his life and that Krause was a
Speaker 1: low-level employee at the time anyways. And she has a point.
Speaker 1: Patel is a man who stole $ 22 million and is
Speaker 1: now trying to stack on top of that another $ 250 million.
Speaker 1: And Patel's case is markedly different than that of Carl Jacobson's.
Speaker 1: Prosecutors made a point at sentencing that not all of
Speaker 1: Patel's spending was the addiction. In fact, huge chunks of
Speaker 1: it were not. $ 78, 000 on private jets, $ 600, 000 at Apple.
Speaker 1: a condo, a Tiger Woods putter. So the detailed account
Speaker 1: of one of these jobs comes from a professional liar
Speaker 1: with a quarter of a billion dollar reason to tell it. Yet,
Speaker 1: the VIP host, the job, it exists. And its sole
Speaker 1: reason for existing is to extract as much money as
Speaker 1: possible from gambling addicts with large bankrolls. But they don't
Speaker 1: always have Large bankrolls. Which brings us to Chris Bruni.
Speaker 1: Chris is 25 years old. He lives in Sheffield, England.
Speaker 1: An electrical engineer making 60,000 pounds a year, he opened
Speaker 1: an account with an online casino called Winner on Boxing
Speaker 1: Day in 2016. That's winner.co.uk. Two days after signing up,
Speaker 1: his VIP host, sent him a free Apple Watch. The
Speaker 1: flytrap wasted no time analyzing Bruni, and it liked what
Speaker 1: it saw. Three days after he opened that account, somebody
Speaker 1: inside the company wrote an internal email noting that Bruni
Speaker 1: was down 22,000 pounds. The regulator later found the company
Speaker 1: had no idea what Chris Bruni did for a living.
Speaker 1: They had not even bothered to ask. Bruni was quickly
Speaker 1: upgraded to the exclusive VIP club, and he was assigned
Speaker 1: a personal account manager. Bruni's debit cards were declining at
Speaker 1: the time. Winner.co could see the card declining. According to
Speaker 1: a regulator's report after his suicide, they discovered that his
Speaker 1: account manager never had a single conversation about the declining cards,
Speaker 1: about if he could afford this little habit. about if
Speaker 1: he might be developing an addiction. That conversation never happened.
Speaker 1: In the five days before he died, Chris Bruni ran
Speaker 1: through 119,000 pounds in his winner.co account and lost it all.
Speaker 1: In those same five days, the company gifted him over 4,500
Speaker 1: pounds in cash bonuses. Chris died on the 5th of April, 2017.
Speaker 1: He left a note, which has never been made public,
Speaker 1: but the record says that it named gambling specifically. That 119,000
Speaker 1: was five days of churn, deposits and losses cycling through,
Speaker 1: and the same money counted and recounted. When they closed
Speaker 1: his accounts and ran the real arithmetic, his actual net
Speaker 1: loss was right around 34,000 pounds, which is 46,000 US dollars.
Speaker 1: half the man's yearly salary. Bad, but survivable. Britain's Gambling
Speaker 1: Commission investigated that company for 18 months and found serious
Speaker 1: systematic failings. In 2016 and 2017, they sent responsible gambling
Speaker 1: emails to about a quarter of 1% of their customers.
Speaker 1: The regulator called that figure exceptionally low. They wanted to
Speaker 1: find the company 3.5 million pounds, but they couldn't. The
Speaker 1: company handed back its license in the middle of the
Speaker 1: investigation and closed their doors permanently. But Great Britain did
Speaker 1: something with this information that no one in the U.S.
Speaker 1: has had the brains, or more likely the guts, to do.
Speaker 1: October 2020. New rules. No VIP scheme can enroll anybody
Speaker 1: under 25. You cannot reward a customer for losing. A
Speaker 1: named senior executive has to personally sign off on these accounts.
Speaker 1: And you have to check whether the person can actually
Speaker 1: afford what they're betting. The number of high-value customers across
Speaker 1: British operators went from about 42,000 to 1,600. That's less
Speaker 1: than 4% of VIP accounts that survived. The United States
Speaker 1: has no such regulations. No federal rules about VIP hosts.
Speaker 1: Now before we get into the next section, I want
Speaker 1: to tell you what broke the spell for me. Remember,
Speaker 1: I was winning. I was up about $ 4, 000 or $ 5, 000
Speaker 1: in a week. Real net bankable money. But the following
Speaker 1: information is what got me to close all my accounts permanently.
Speaker 1: These sportsbooks are extraordinary at spotting a pattern. If you
Speaker 1: start winning, If your betting shows the signature of somebody
Speaker 1: who actually knows what they're doing, they find you and
Speaker 1: they shut you down. Not banned, exactly, but limited. Your
Speaker 1: maximum bet drops to $ 5, maybe $ 20. You're still a customer,
Speaker 1: but you can't hurt them. Fanatics disclose that almost half
Speaker 1: the customers it had limited were actually losing money at
Speaker 1: the time it limited them. They don't always cut winners. Sometimes,
Speaker 1: Many times, early winners are their most profitable long-term customers.
Speaker 1: They cut off people whose pattern looks like they might
Speaker 1: win later. This is the machine. There's no door out
Speaker 1: of it marked winner. Lose small, you're scenery. Start winning,
Speaker 1: you're limited. Lose big, you're the business. 1,366 deposits. Nobody
Speaker 1: limited that. because that's the machine working exactly as it
Speaker 1: was designed. The state asked FanDuel and DraftKings what Carl
Speaker 1: Jacobson bet, and the companies answered to the penny across
Speaker 1: a full year. Nobody asked them who talked to Carl.
Speaker 1: There's no line in those 10 pages about a VIP host,
Speaker 1: a text at 11 p.m. at night after a day
Speaker 1: of account inactivity, But just because it's not in those
Speaker 1: 10 pages doesn't mean it doesn't exist. There was one
Speaker 1: place in time, one moment where these types of questions
Speaker 1: were going to get answered out loud on the record.
Speaker 1: Patel's lawsuit. Discovery would have opened the internal messages, the
Speaker 1: compliance conversations, what the hosts are told to do, what
Speaker 1: they actually do. In May of this year, a federal
Speaker 1: judge sent that case online. private arbitration. So the answers
Speaker 1: are out there. Maybe not in the Patel case, but
Speaker 1: it's only a matter of time before we start getting details.
Speaker 1: In the meantime, I can tell you about mine. 10 days,
Speaker 1: 9 sportsbooks, and the offers came all day long. I
Speaker 1: don't think I had quite stuck around long enough to
Speaker 1: get a VIP host. I also probably hadn't lost enough
Speaker 1: money yet. But, I got boosts, second chances, a little
Speaker 1: something after a loss, 10 days in and I was
Speaker 1: worth chasing. But not for every sports book. Five or
Speaker 1: six of them didn't like how I was betting. Those
Speaker 1: early measured bets where I was finding an edge, taking
Speaker 1: both sides, playing promos off each other. A lot of
Speaker 1: those books didn't like what they saw. They didn't limit
Speaker 1: me yet, but I limited myself. Because they stopped sending
Speaker 1: promos and I stopped betting on those apps. FanDuel and Fanatics,
Speaker 1: those were the two that kept the promos coming. Almost
Speaker 1: twice a day, maybe more from each of them, I
Speaker 1: would get an email or notification of a profit boost,
Speaker 1: odds boost, or free bet. I went looking for those
Speaker 1: emails specifically for this episode, but they're gone. When I
Speaker 1: stopped betting and self-excluded from all the sportsbooks, I deleted
Speaker 1: all the emails, blocked all the addresses. So the only
Speaker 1: evidence I have that a machine was working on me
Speaker 1: is that I remember it working on me. Now, the
Speaker 1: other side of the pancake. Nobody at those companies made
Speaker 1: Carl Jacobson write a check to himself. The offers are
Speaker 1: what they say they are. And there are people, non-addicts,
Speaker 1: who occasionally take it use it, and walk away. The
Speaker 1: person sitting in that VIP manager gig has a sales target,
Speaker 1: a family of their own, and if you ask them,
Speaker 1: they tell you, honestly, that they work in customer relations.
Speaker 1: Because they do. They are extremely good at customer relations.
Speaker 1: And that's the problem. If you've never held a secret
Speaker 1: like this one, it's easy to miss what's really for sale.
Speaker 1: A man betting money he cannot afford is an unknown man.
Speaker 1: Others don't know him. He doesn't know himself. You edit
Speaker 1: every conversation. You quietly mute the phone at family dinners.
Speaker 1: The people who love you get a version of you,
Speaker 1: but not the whole you. Which means the person from
Speaker 1: the sports book, the one who has the real numbers
Speaker 1: in front of them, is the only person who knows
Speaker 1: the truth of your life, what it's become. And they're
Speaker 1: not upset about it. Everyone who loves you would be horrified.
Speaker 1: But this voice isn't. No flinch, no lecture, no tears
Speaker 1: at the kitchen table. Approval from the only one who knows.
Speaker 1: For a person carrying a secret that heavy, that's a
Speaker 1: drug all by itself. Three assistant chiefs worked down the
Speaker 1: hall from Carl Jacobson for years, and though they, at times,
Speaker 1: suspected something was wrong, they didn't know what it was.
Speaker 1: His command staff didn't know. Whoever he came home to
Speaker 1: at night didn't know. But a server in Boston knew
Speaker 1: the hour, knew the amount, knew when it got worse.
Speaker 1: knew and had no reason on earth to do anything
Speaker 1: about it except exploit it for maximum profit. The reason
Speaker 1: any of this was legal in the first place, Connecticut
Speaker 1: gets a cut. That's the deal. The state legalized these
Speaker 1: apps in 2021, and in exchange, it taxes what they make.
Speaker 1: Every screen Carl Jacobson tapped had a sliver of state
Speaker 1: revenue riding on it Jonathan Cohen, the guy who wrote
Speaker 1: the book on sports betting, did the arithmetic on that cut.
Speaker 1: On a whole, Connecticut takes $ 26. 5 billion in tax revenue yearly.
Speaker 1: Now let's go to 2023, the first full year of
Speaker 1: legalized online gambling in the state. Connecticut's cut was $ 273 million.
Speaker 1: Not a small number by any means, but in terms
Speaker 1: of total revenue that the state took in, That's almost
Speaker 1: exactly 1%. Cohen's words, a drop in the bucket. But
Speaker 1: the number is growing. In 2024, state revenue jumped from
Speaker 1: 273 to 400. And the following year, 528 million. Carl
Speaker 1: is not alone. Connecticut is recruiting hundreds, thousands of people
Speaker 1: just like him. Carl. So that's the deal. The machine
Speaker 1: operates legally in Connecticut and many other states just like
Speaker 1: it because it contributes one, maybe two percent of the
Speaker 1: annual tax revenue. And to the machine, Carl Jacobson's year,
Speaker 1: the $ 214, 000 he lost is a rounding error inside the drop.
Speaker 1: After the Randy Cox thing, Carl Jacobson built the reforms
Speaker 1: you heard about last episode He made sure it was
Speaker 1: put down in writing. In a policy, if a person
Speaker 1: in your custody tells you they're hurt, you have to
Speaker 1: ask them about it. You have to call for help
Speaker 1: if they request it. Codified in Special Order 22-03, quote.
Speaker 5: Requiring all officers to make an initial inquiry to determine
Speaker 5: whether a prisoner is injured and or needs medical assistance.
Speaker 5: If a prisoner is injured or requests medical attention prior
Speaker 5: to transport, the officers must immediately contact their supervisor and
Speaker 5: request that an EMS be dispatched to their current location.
Speaker 1: Carl made that law, and then he went home to
Speaker 1: a tiny screen. On day 11, I called somebody. You
Speaker 1: already know that. Carl Jacobson was who people called. He
Speaker 1: said he fixed the drinking. And I believe him. The
Speaker 1: wall held. The water went around it. In March, Carl
Speaker 1: stood in front of a judge and agreed to the
Speaker 1: conditions of his release. Show up, don't leave the state,
Speaker 1: and no gambling, online or in person. Somebody finally told
Speaker 1: Carl Jacobson to stop. It took a felony charge, an
Speaker 1: FBI accountant, and $ 85, 500 that wasn't his. In April, he
Speaker 1: pleaded not guilty and asked for a jury outside the
Speaker 1: courthouse for the first time since his arrest. He apologized
Speaker 1: to the mayor, to the city, to his officers. A
Speaker 1: reporter asked him how he could plead not guilty to
Speaker 1: something that he was apologizing for. And, well, here's what
Speaker 1: he had to say.
Speaker 4: Officers, that's my biggest concern. You know, I.
Speaker 4: I just hope that the community and the officers can
Speaker 4: move forward and, you know, still do what they were
Speaker 4: doing together when I was chief. And, you know, I
Speaker 4: wish everybody luck. And I hope that, you know, I
Speaker 4: care about the officers. And then obviously with my situation,
Speaker 4: there was things that I didn't take care of personally.
Speaker 4: And I was, as chief, trying to get more services
Speaker 4: for the officers. And I just hope that if anything
Speaker 4: is learned from this that these officers need, um, it's
Speaker 4: a hard career and they need help and we got
Speaker 4: to keep, take care of them as we move forward.
Speaker 3: What do you have to say to the city? What
Speaker 3: do you have to say to the mayor who had
Speaker 3: faith in you?
Speaker 4: Yeah, you know, um, I apologize to the mayor and
Speaker 4: the city and the officers.
Speaker 2: But Carl, can you explain in the arrest warrant, there
Speaker 2: is some admission there, but you plead not guilty today.
Speaker 2: Can you explain that?
Speaker 4: It's just part of the court process. I mean, um,
Speaker 4: You know, at this point, it's early in the stage, and,
Speaker 4: you know, basically, I don't want to comment further on that.
Speaker 4: That's more of my lawyer's part.
Speaker 2: Anything else you'd like to say to the viewers of Connecticut,
Speaker 2: obviously the people in the city who believed in you
Speaker 2: and trusted you?
Speaker 4: Yeah, no, I, you know, I apologize. I love this city.
Speaker 4: I hope this city moves forward. I hope the officers
Speaker 4: move forward. And that's all.
Speaker 3: Thank you.
Speaker 2: I mean this with respect. Is there anything you can
Speaker 2: say about, like, you know, trying to tell people why
Speaker 2: you did.
Speaker 4: What you did? I really can't get into that now.
Speaker 4: I mean, it wasn't intentional. It wasn't something that I
Speaker 4: really can't get into it now.
Speaker 2: Gambling these days is such a serious thing and is
Speaker 2: affecting a lot of people. I mean, can you shed
Speaker 2: some light into just how serious of an issue it is? Well, yeah.
Speaker 4: I mean, it's something that obviously has been popping up
Speaker 4: all over the news, and it was something that I
Speaker 4: got caught up in. with the ease of having it
Speaker 4: on an app. So, you know, I just hope people understand,
Speaker 4: if anything, learn from the cases that are coming up
Speaker 4: recently to make sure they take care of themselves.
Speaker 2: Is that something you are looking to get help for
Speaker 2: or seek some help for in Connecticut? I know there
Speaker 2: are some resources in the state.
Speaker 3: Oh, yeah.
Speaker 4: Yeah, I don't want to comment further on that either,
Speaker 4: but thank you guys. Thank you. Thank you.
Speaker 1: The affidavit is 10 pages long. I want to tell
Speaker 1: you how it ends. Not with a four and a
Speaker 1: half million. Not with the memo line. The last thing
Speaker 1: Lieutenant Wardell wrote is that because of Carl Jacobson's pattern
Speaker 1: of behavior, additional search warrants have been drafted, signed, and
Speaker 1: executed with expanded time parameters covering the years prior to 2024.
Speaker 1: Carl had control of that fund, that money, since July
Speaker 1: of 2019. He appeared in a New Haven courtroom just
Speaker 1: a few weeks ago, August 4th. He was issued a
Speaker 1: continuance September 14th. Next time, the final episode of The
Speaker 1: App on the Phone. Thank you for listening. My name
Speaker 1: is TZ. and I'm the host of Tapes from the
Speaker 1: Dark Side. If any of tonight hits home, if you're struggling,
Speaker 1: please consider reaching out to the National Problem Gambling Helpline, 1-800-GAMBLER.
Speaker 1: It's free, 24 hours. I want to get this episode
Speaker 1: out to you as quickly as possible, so no more credits.
Speaker 1: Do the credits in the finale. Thank you for listening.
Speaker 1: Until next time, try to enjoy the daylight.
Speaker 3: We've won a couple for about that amount. A couple
Speaker 3: for $ 600.
Speaker 4: Yes.
Speaker 3: So it more than paid for itself.
Speaker 4: Yes.
Speaker 3: I assume.
Speaker 5: Yes.
Speaker 3: That's why you keep playing. Lucky people. We've lost a
Speaker 3: few too. We've lost a few too. Oh, I can imagine.
Speaker 3: People usually only talk about their wins. Absolutely.