June 29, 2026
S12, Chapter 1: The App on the Phone
Everyone remembers their first win. I remember mine. The chief of police of New Haven, Connecticut surely remembered his. And in the twelve months that followed, he wagered $4.4 million on sports betting apps from the phone in his pocket. This is...
Everyone remembers their first win. I remember mine.
The chief of police of New Haven, Connecticut surely remembered his. And in the twelve months that followed, he wagered $4.4 million on sports betting apps from the phone in his pocket.
This is the story of Karl Jacobson's fall, told alongside my own 10-day descent into the same apps. Come and see what Karl felt from the inside, and the devastating lesson I learned with him: the most dangerous part of gambling isn't losing. It's winning.
The App on the Phone is the new season from Tapes from the Darkside.
For the first time, you can download/stream this episode as a lossless WAV file, the exact uncompressed quality I master it in.
https://www.patreon.com/tapesfromthedarkside
If you or someone you know is struggling with gambling, the National Problem Gambling Helpline is available 24/7 — call or text 1-800-522-4700. Free and confidential.
Credits and Sources
Editing help by:
Troy Piano on Airgigs.com
Archival audio & media
* Karl Jacobson interview — Dateline New Haven, WNHH-LP FM (New Haven Independent community radio), 2022–2023
* Karl Jacobson swearing-in remarks — [broadcaster/source to confirm]
* New Haven Police Department press conference on the Jacobson charges — [broadcaster/source to confirm]
* Duke vs. UConn, NCAA Tournament Elite Eight game call — [network to confirm: CBS/TBS/TNT]
* Sports betting advertisement (FanDuel/DraftKings promotional spot) — [advertiser to confirm]
Reporting & court records
* Arrest warrant affidavit, State of Connecticut v. Karl Jacobson, Connecticut State Police, February 2026
* New Haven Independent (Thomas Breen reporting), 2026
* University of New Haven, "Father and Daughter Share a Passion for Criminal Justice," December 2021
Scientific & academic sources
* Clark, L., et al. "Gambling Near-Misses Enhance Motivation to Gamble and Recruit Win-Related Brain Circuitry." Neuron, 2009.
* Diagnostic and Statistical Manual of Mental Disorders, 5th ed. (DSM-5), American Psychiatric Association, 2013 — reclassification of gambling disorder.
* Nathan Novemsky, Yale School of Management — commentary on Connecticut sports-betting legalization.
* Research on DRD2 Taq1A allele and addiction heritability; twin-study heritability estimates for gambling disorder.
* U.S. sports betting market figures (American Gaming Association data, 2017–2024).
Music
* Matooma — "Infinite Emptiness"; CTRL S — "SpaceTimeThought"; Shahead Mostafafar — "Into the Next Dimension"; Jamie Bathgate — "Atmo"
* AUGUSTA TREVERORUM — from the album 1991. agsttrvrrm.bandcamp.com
* 20SIX Hundred — "Cimmerian Shade / Last Moments," from the album The Cold Rise From Sleep (2015). Used with permission / licensed. 20sixhundred.bandcamp.com
Special thank you to:
Uncle Chris for his post credit contribution.
WEBVTT
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It's getting dark outside.
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Tapes from the Dark Side.
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Contains descriptions of violence and sexuality. Listener discretion is advised.
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I don't even remember who is playing. I just remember
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the green and blue of the fan dual interface, the
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three hundred dollars number on the screen, and my thumb
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hovering over the button. But I honestly don't remember losing.
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That's the part nobody tells you about gambling addiction. Nobody
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remembers their first loss. It slides off you like water
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off a dead man's back. It's nothing, it's a shrug.
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Your brain doesn't even bother filing it away. But your
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first win you remember that. The best way I can
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put it is it's kind of like the first time
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someone you trust puts their hand on your throat. You
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remember it not because it hurt, but because part of
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you liked it. Everyone remembers their first win. On January fifth,
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twenty twenty six, a man sat in a conference room
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in New Haven, Connecticut. Three of his closest colleagues were
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across the table. He had been their boss for two
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and a half years. One of them had a cell
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phone in his pocket, recording because he was afraid of
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what this man might do. When confronted, the man looked
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at them and said, and I'm quoting directly from a
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secretly recorded audio tape that is now part of a
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criminal case file quote.
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I have a problem. I fixed my alcohol problem. I
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turned to gambling. I don't know why. It just got
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worse recently.
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That man was the chief of police of New Haven, Connecticut.
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His name was Carl Jacobson, and in the twelve months
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before that conversation, he had wagered four point four million
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dollars on sports betting apps on his phone. Four million,
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four hundred and sixty four thousand, eight hundred and eighty
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four dollars. That number will follow Carl Jacobson for the
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rest of his life.
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I think everyone has a bit of a fascination of
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the dark side.
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I myself laws he loved the dark side as well.
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I think it's something that ever want to secretly longs
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for an months.
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To say that this news is a shock. As an understatement,
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it's a shock to me. It's a shock to the
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command staff. It's a shock to the men and women
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of the police department. It's a shock to the New
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Uban community.
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It was late March twenty twenty six, and March Madness
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was in full swing. If you watch sports, if you
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even casually follow sports, you know what March looks like.
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Now.
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Every time out is a DraftKings ad. Every halftime is
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a FanDuel promo. To my international listeners who might be unfamiliar,
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March Madness is a national college basketball tournament, single elimination.
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The whole country watches, and my personal favorite thing about
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March Madness are the Cinderella stories, the under dogs, and
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I love a good underdog. I don't remember where I
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saw the first ad. It might have been scrolling on Instagram.
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It might have actually been one of the timeouts on TV,
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but the offer caught my eye, not because it was
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necessarily flashy and featuring John Ham, but because, if you
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understand math at all, this looks like free money. That
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phrase free money might just be the most dangerous pair
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of words in the English language. It's the worm on
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the hook, the proverbial candy in the van.
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Ooh betting in space.
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New customers get up to three hundred dollars back in
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bonus bets every day for ten days.
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If your bets don't win.
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Here's how it works. You place a bet let's say
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three hundred dollars on a money line. If it wins, great,
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you keep your three hundred dollars steak and you keep
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the winnings. That's the best outcome. But if it loses,
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you don't automatically forfeit that three hundred dollar initial bet,
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because the next day FanDuel gives you what they call
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a bonus bet, three hundred dollars to bet on anything
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you want. If that bonus bet hits, then you keep
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the profit, not the three hundred dollars steak. So the
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backup plan is a worse deal, but it increases your
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odds of winning drastically. This promo ran for ten days,
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one three hundred dollars bet reset token per day. Now,
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I honestly had no intention of using it more than once.
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I just wanted to make one March Madness game a
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little more interesting. If you bet and win, great, But
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if you bet and lose, you get a second chance.
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The absolute worst case scenario is I'm out three hundred dollars,
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not a small sum for a guy like me, But
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unlike the vast majority of gambling, the odds are actually
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in your favor, and at three forty in the morning
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on March twenty ninth, I placed that first bet, three
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hundred dollars on Tennessee over Michigan in the Elite eight
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plus two sixty. That's which call a long shot. It
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wouldn't be until about ten days later that I realized
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what actually happened In that moment. Something deep in my
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psyche was stirring. Later that day, Tennessee lost, but my
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three hundred dollars wasn't gone. Instead, I got the consolation prize.
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The next day, a bet reset token kicked in, and
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now I had three hundred dollars in bonus money sitting
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in my fan duel account. I needed to pick another game.
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This time I picked another underdog, Yukon over Duke money
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line plus one eighty four. And what happened in that
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game matters not for the basketball, but for what it
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did to my brain.
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There is one spot remaining and one game left of
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the determined who goes to the final four.
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Duke was up big at halftime, forty four to twenty nine.
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Number one Seeds had been one hundred and thirty four
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and zero in tournament games where they led by fifteen
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points or more at half.
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So a forty four to twenty nine, advantage for Duke
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and Yukon trying to climb out of this deep hold.
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Yukon's win probability at this point in the game was
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one point three percent, and then Yukon came back.
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Yukon down by as many as nineteen, they have a
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chance to cut it to two. The pressure is building now.
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Yukon erased a nineteen point deficit, the largest comeback ever
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against a number one seed in that situation, and with
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four tenths of a second left, a freshman named Brayln Mullins,
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who was nineteen years old, a literal teenager, launched a
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three pointer from thirty five feet away, still avous caravan.
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Two seconds LUNs tosses it up.
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Why by y y Youn's not funningly.
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Utterly impossible over ukh still has the yard.
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Tragic Yukon seventy three, Duke seventy two. I won two
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hundred and fifty two dollars on a bonus bed on
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a game with a one point three percent win probability
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at halftime, And what ended up being important in that
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moment was not what happened on screen, but what happened
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inside me, Because something lit up that I hadn't felt
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in a long time, A warmth, a vibration in my
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rib cage that said, do that again, the way a
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dog here's a frequency you can't, the way a corpse
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flower knows when to bloom after ten years nothing. What
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happened to me in that moment has a clinical name.
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It's called a dopamine response. More specifically along the Mesolympic pathway.
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It was more important than the money, more important than
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the apps, because that feeling that I got from watching
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Brayln Mullen's shot go in is the same feeling that
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grabbed the subject of our story. It's the first hit,
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and for some people, for people with brains like mine,
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it's the only hit the machine ever needs to give you.
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That exact feeling grabbed a man named Carl Jacobson. The
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difference is what we brought to the table when it
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hit us and what was waiting on the other side.
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Carl Jacobsen was, by every external measure, exactly the kind
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of person you want running your police department. He was
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fifty five years old, a New England native. He had
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twenty seven years in law enforcement, nine years with the
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East Providence Police Department, starting in nineteen ninety eight, then
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the New Haven Police Department from two thousand and seven onward.
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Reclimbed from patrol officer to sergeant, to lieutenant to assistant chief.
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Along the way, he earned a US Attorney's Director Award
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in a National Association of Police Organization's Top Cop Award.
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These are not participation in trophies. These are recognitions given
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to officers who have done exceptional work. In May of
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twenty twenty two, after a nationwide search for a new
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police chief, New Haven Mayor Justin Ellicker chose Carl. He
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didn't pick someone from LA or Chicago or New York.
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He picked the local guy, the one who'd been in
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the department for fifteen years. Carl was sworn in as
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chief on July sixth, twenty twenty two.
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So help me God, congratulations.
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When I started this journey of public safety, I had
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one goal in mind, and that was to make others
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feel safe. As chief as my responsibility to ensure that
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this department remains transparent and accountable and works for the community.
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He lived in Branford, Connecticut, with his wife, Dawn. They
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had two children, an older son named Carl and a
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daughter named Kelly.
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Hello, and welcome to Daylon New Haven and WNAHHTFM, new
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Haven's home for community radio. Today we have a man
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who is New Haven's new police chief, Carl Jacobson. Thanks
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so much for coming on the end of on WNHH.
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Thanks for having me, Paul, It's good to be here.
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Like a chief, you had a pretty early on recommend
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firing some people who you personally liked. What was that, Like,
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how do you do that?
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Yeah?
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I mean since I've been chief, three people have been fired.
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There's a couple more that's been recommended to be fired
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on It's hard because you make connections with people and
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they work for you. But then when you have I
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have like people tell you the story and the stories
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like really over the top. And then and it was
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in this situation, it was just a matter of just
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telling the truth and and you're like what are you doing?
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You know, and you know, we're all human and we
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make mistakes. So I'm not looking to fire people, but
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I'm telling you the since the Randy Cox thing in
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the incident that you're talking about, you have to treat
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the community with respect and dignity. That's what it comes
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down to. If the officers did that in these different
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cases there would be a bit a different outcome. It
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almost sounds simple, Paul, give people a voice, treat them
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with dignity, neutrality and decision making. So you go to
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a call and even.
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At the time of that interview, Carl Jacobson was already gambling.
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The warrant would later reveal that in the year following
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this conversation alone, he wagered more than four million dollars,
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and investigators believe it started long before that. But you
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can't hear it in his voe. There's no tremor, no desperation,
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no tells. That's the thing about this disease. It doesn't
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alter your behavior like drugs or alcohol. In fact, it
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makes you sound fine. It makes you sound exactly like yourself,
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right up until the moment the floor gives out. In
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December twenty twenty one, the University of New Haven published
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a Future Story about a father and daughter who shared
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a passion for criminal justice. Carl Jacobson and his daughter, Kelly,
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were attending the University of new Haven at the same time.
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Carl was completing his Master of Science and criminal justice
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and Kelly was starting her undergrad degree, also in criminal justice.
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At the University's Henry C. Lee College of Criminal Justice
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and Forensic Sciences. They were in the same program the
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same time at the same school. Kelly told the university,
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and I'm quoting her directly.
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It's been great earning a degree while my dad is too.
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We're definitely able to bond over it, and sometimes we
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even get competitive about who has the better grades. Carl said,
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I am extremely proud of my daughter, who is a
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hard worker and a dedicated person.
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Kelly wasn't just getting by. She was a field hockey
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player with a three point nine GPA. She was named
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a National Field Hockey Coaches Association Scholar of Distinction. She
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told the university that her father's dinner table stories about
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policing were what inspired her to major in criminal justice
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in the first place. By twenty twenty three, Kelly Jacobson
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wanted to become a New Haven police officer. She wanted
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to follow in her father's footsteps. Within three years of
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that university feature, Carl Jacobson will be arrested for stealing
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eighty five thousand dollars from the City of New Haven,
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including four thousand dollars from a fund that paid for
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children's basketball clinics and summer camps, written as checks to
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himself at Christmas time. But we're not there yet, not
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even close. Right now, in this moment, Carl Jacobson is
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a decorated police chief with a master's degree, a proud father,
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and a promising career. He is truly living the American dream.
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A nice house Connecticut, his wife and kids. He goes
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to work every day and tries to make Newhaven safer,
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and somewhere, underneath all of it, something was already wrong.
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Something had been wrong for a long time, the kind
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of wrong that doesn't make noise. It just sits in
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the walls, like black mold, growing until one morning you
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peel back the wallpaper. We'll be back after a quick break.
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If you want to skip the ads and support the
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