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

—

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.

—

Support the show:

patreon.com/tapesfromthedarkside

—

Audio Sources:

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

—

Music Credit:

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

Augusta Treverorum
https://linktr.ee/trvrrm

—

Follow me.

https://www.instagram.com/thedarksidepod/
https://www.facebook.com/tapesfromthedarkside/
https://www.facebook.com/groups/tapesfromthedarkside

—

More links.

Leave us a Review (...it really helps!)
https://www.tapesfromthedarkside.com/rate/

PayPal Donations
https://www.tapesfromthedarkside.com/paypal/

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.

Support us on Patreon:
patreon.com/tapesfromthedarkside

Make a PayPal donation:
https://www.paypal.com/donate/?hosted_button_id=CQC9VPG9RZ9AW

Merch:
https://tapesfromthedarksidepod.dashery.com/

Follow me:

• https://www.instagram.com/thedarksidepod/
• https://www.facebook.com/tapesfromthedarkside/
• https://www.facebook.com/groups/tapesfromthedarkside

Sources:
https://www.partnersintruecrime.com/


Music Credit:

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

No credits this week because I didn't want to delay this episode any longer.
For their plan to work, Larry Bittaker knew they couldn’t rely on just any car. They needed something bigger… something that could trap a victim inside. In February of 1979, with money from Norris, he bought it—a silver-gray 1977 GMC Vandura.

The van was windowless on one side, with a sliding door large enough to swallow someone whole. Bittaker later admitted that when he first saw that door, he knew. They could pull up close to a girl, slide it open, and drag her inside without anyone noticing.

The pair gave the vehicle a name. To them, it wasn’t just a van. It was their “Murder Mac.”

—

Patreon:
https://www.patreon.com/c/tapesfromthedarkside

—

Sources:

Partners in True Crime
https://www.partnersintruecrime.com/

Music:

Augusta Treverorum
https://linktr.ee/trvrrm

Two men are locked inside the California Men’s Colony — a medium-security state prison tucked away in the rolling hills of San Luis Obispo.

It wasn’t a fortress like San Quentin.

It didn’t house the state’s most violent criminals.

And its reputation was far from what you’d expect of a place that would soon become a breeding ground for one of the most sadistic criminal partnerships in modern history.

Support the show!
http://patreon.com/tapesfromthedarkside

—

Sources:
https://www.partnersintruecrime.com/

Music Credit:
Augusta Treverorum
https://linktr.ee/trvrrm

BABY-DOLL-BEATZ
https://www.youtube.com/@baby-doll-beatz
https://www.youtube.com/@lovechapo

Two men. Five girls. One summer of calculated, incomprehensible cruelty.

This is the story of The Toobox Killers. (If you think you already know this story you might be surprised.)

—

Support the show
patreon.com/tapesfromthedarkside

—

Get 60% off the Magic Mind offer with our link and code https://magicmind.com/tapesmf & TAPES60 #magicmind #mentalwealth #mentalperformance


Sources:
https://www.partnersintruecrime.com/

Music Credit:

Augusta Treverorum
https://linktr.ee/trvrrm

BABY-DOLL-BEATZ
https://www.youtube.com/@baby-doll-beatz
https://www.youtube.com/@lovechapo

In the suburbs of Long Island, behind the quiet streets and manicured lawns, something dark was festering. Joel Rifkin, a man with a soft voice, thinning hair, and a passion for gardening, harbored a secret—one that would horrify the nation.

Support us on Patreon. New sliding scale memberships now available from $3-7.
https://www.patreon.com/tapesfromthedarkside

New merch store.
www.tapesfromthedarkside.com/merch

Works cited:
https://www.imdb.com/title/tt15966204/

(00:00:00) Unsportsmanlike Conduct

(00:00:19) chapter 1

(00:04:38) chapter 2

(00:13:07) chapter 3

Three tales of rage and ruin in the sports world.

Chapter 1 = The Gruesome Death of Otavio da Silva
Chapter 2 = Bruiser Brody
Chapter 3 = Snook

Support the show on Patreon!
www.patreon.com/tapesfromthedarkside

—

Follow on instagram for behind-the-scenes and updates.
https://www.instagram.com/thedarksidepod/

—

Music Credit:

Augusta Treverorum
https://linktr.ee/trvrrm

BABY-DOLL-BEATZ
https://www.youtube.com/@baby-doll-beatz
https://www.youtube.com/@lovechapo

Eighteen-year-old Becky Thomson Brown grabbed her keys and asked her 11-year-old half-sister, Amy Burridge, if she wanted to come along for a quick grocery run.

It was a trip that would ultimately change both of their lives forever.

—

Support us on Patreon:
https://www.patreon.com/tapesfromthedarkside

—

Follow on instagram for behind-the-scenes and updates.
https://www.instagram.com/thedarksidepod/

—

Credit to:

https://rapidcityjournal.com/1973-murder-and-rape-have-lasting-effect-on-family-casper/article_a102350c-fd54-58a1-8ee9-12a0e335f56f.html

https://www.latimes.com/archives/la-xpm-1992-08-23-mn-7229-story.html

https://www.washingtonpost.com/archive/politics/1992/08/13/a-crimes-lasting-wounds/f4cd227d-d5dc-422f-bf3c-99ccbcd5ad3b/

—

For comments or corrections, please email:
[email protected]