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.