Tapes from the Darkside

Nine apps. Ten days. Hundreds of bets.

I'll walk you through what a gambling spiral looks like firsthand. We'll take a look at the $314 million machine that put these apps in front of me. And the illusion of control that almost turned a ten day experiment into something that much much worse.

Karl Jacobson wasn't so lucky.

His childhood; filled with alcoholism and abuse. As a cop, he spent his life trying to become the kind of person who makes others feel safe. The person you can trust.

And the disease that lived in his childhood home found him anyway. Not through a bottle, but through a screen.

Resources
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.

Patreon
Support the show and get access to the Premium Feed. Bonus episodes. Early, ad-free, lossless.
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Merch store relauch. Everything is on sale for a limited time.
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Credits and Sources

Editing help by:
Troy Turner / troypiano at https://www.airgigs.com/user/troypiano

Interview Clips
Karl Jacobson — "Kica's Corner: Police Chief Karl Jacobson" (Kica Matos, YouTube, ~mid-2022).
Karl Jacobson — "Karl Jacobson speaks on new role as New Haven Chief of Police / Full Interview" (swearing-in, July 2022).
Legislative / Documentary Footage
U.S. Senate Judiciary Committee Hearing on Legalized Sports Gambling (December 2024). Senator Dick Durbin.
Predatory Gambling Documentary — "The Big Con" segment. Les Bernal and others on the financial-exchange model of commercialized gambling.
Betting Advertisements (as cited in the episode)
FanDuel television ad
BetMGM television ad ("Make it legendary")
DraftKings television ad (featuring Kevin Hart)
Bet365 television ad ("Bet $10, get $365")
DraftKings television ad ("New customers bet five bucks, get 300")
Research & Studies Referenced
Ellen Langer (1975), "The Illusion of Control." Journal of Personality and Social Psychology 32(2), 311–328. doi.org/10.1037/0022-3514.32.2.311
B.F. Skinner, Schedules of Reinforcement (Ferster & Skinner, 1957).
American Gaming Association, Responsible Marketing Code — barred members from using "risk free" (and "free bet") language. americangaming.org
LaBrie, LaPlante, Nelson, Schumann & Shaffer (2007), "Assessing the Playing Field: A Prospective Longitudinal Study of Internet Sports Gambling Behavior." Journal of Gambling Studies 23:347–362.
Braverman & Shaffer (2012), "How Do Gamblers Start Gambling: Identifying Behavioural Markers for High-Risk Internet Gambling." European Journal of Public Health 22(2):273–278. doi.org/10.1093/eurpub/ckp232
Nelson et al. (2019), "Longitudinal Playing Trends Among Daily Fantasy Sports Players." Computers in Human Behavior. sciencedirect.com
"A Large-Scale Prospective Study of Big Wins and Their Relationship with Future Financial and Time Involvement in Actual Daily Fantasy Sports Contests" (2021). pubmed.ncbi.nlm.nih.gov/33734785
Lesieur & Custer (1984), "Pathological Gambling: Roots, Phases, and Treatment." Annals of the American Academy of Political and Social Science 474:146–156. journals.sagepub.com
Michael Sandel, Justice: What's the Right Thing to Do? (Harvard University; lecture series and book).
r/problemgambling — User GamblingRecoveryCom: "Gambling is a paradox where losing is actually the best-case scenario. Winning early is an infection."
Music
20SIX Hundred — "Cimmerian Shade / Last Moments," from the album The Cold Rise From Sleep (2015). Used with permission / licensed. 20sixhundred.bandcamp.com
AUGUSTA TREVERORUM — "Nightmares" from the album Blacktape. agsttrvrrm.bandcamp.com
Matooma — "Infinite Emptiness"; CTRL S — "SpaceTimeThought"; Shahead Mostafafar — "Into the Next Dimension"; Jamie Bathgate — "Atmo"; DaniHaDani — "Aurora". Licensed via Artlist. artlist.io
Just for Kicks — "TV Dinner" (Creative Cut, "Dreamy") and "Why Am I Anxious." Licensed via Artlist. artlist.io

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.

This is the final episode in the Toolbox Killers series. Thanks for your patience.

A new series is coming soon.

patreon.com/tapesfromthedarkside

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For those curious, explanation of where I've been:
https://www.patreon.com/posts/155116830

"We've all heard women scream in horror films ... still, we know that no-one is really screaming. Why? Simply because an actress can't produce some sounds that convince us that something vile and heinous is happening. If you ever heard that tape, there is just no possible way that you'd not begin crying and trembling. I doubt you could listen to more than a full sixty seconds of it."

Roy Norris, describing his recollections of the audio tape the pair had created of Shirley Ledford's rape and torture.

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Support the show:

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Audio Sources:

The Toolbox Killer (2021)
https://www.imdb.com/title/tt15575214/

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Music Credit:

20six Hundred
https://20sixhundred.bandcamp.com/

Augusta Treverorum
https://linktr.ee/trvrrm

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It was the summer of 1979. The last vestiges of the 1970s were set to expire and welcome in the rip and roar era of the 80s.  This chapter takes place in Torrance, California, a coastal town where the air smells faintly of salt and sun-baked asphalt.  The streets glow soft orange beneath the high pressure sodium streetlights.

Sixteen-year-old Lucinda Lynn Schaefer walks those streets often, the kind of girl who never seems out of place anywhere.  Her friends call her Cindy. Blonde hair, bright blue eyes, always with a book tucked under her arm or a quick smile ready to disarm a stranger.

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Sources:
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Music Credit:
Augusta Treverorum - https://linktr.ee/trvrrm
20Six Hundred - https://20sixhundred.bandcamp.com/