In the season finale, I go back to day 11... the $500 bet reset token the app sent me the day I was supposed to quit, and the coffee shop where I decided my sponsor was the enemy. I'll also play you a voicemail my cousin left me, with four words in it that Karl Jacobson said about himself as his career was ending. Then, with his larceny case still open, Karl asked New Haven to make his pension tax-free.

It feels good to support the things you love. That's why I'm asking you to support TAPES FROM THE DARKISDE by joining us on Patreon. Memberships are $3 / month for the next 48 hours before we move our entry DARKSIDER tier to $6 monthly.

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Karl Jacobson has been charged and has not been convicted.  Charges are allegations.  The account in this series comes from the sworn arrest warrant affidavit, court and city records, and public reporting.

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.

Or if you're somewhere darker than that. Call or text 988. Suicide and Crisis Lifeline, 24/7.

Credits

Hosted, written, and produced by T. Z. Borden.

Executive producers: Greg B, Sundeen, Jessica Wagner, Ann K, and Allison Barkley.

Associate producer: Lindsey Choy.

Our new Darksiders:

• $7: Dave Humes, Chrissy Cosgrove, Alice Margaret Prout, Marcus Butler, David Fox, Holly Deaton
• $5: Em, Lisa Brannen, Emily Matthews, Landy Anderson, Sturgy, Robert Eff, Jim Hillard, Kristen, AllieD, Diane K H
• $4: Toby, Cameron Mackay
• $3: Chasing Amy in the Dark, Sam, Sunday A, Samantha Booth, Allison Newton, Molly Mackay, RLCH, Johanna Vespe, Justin Briggs, Jake Lee

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
• Baby-Doll-Beats / Love Chapo — https://www.youtube.com/channel/UCtGc3VPRShmnSt8mq6I7fCQ

Merch

We relaunched our merch store. Treat yourself to something from the DARKSIDE.
https://merchfromthedarkside.com/

AUDIO IN THIS EPISODE

"New Haven Police Chief Karl Jacobson's Epic Speech at Memorial Ceremony," The Handler (YouTube). Poem by Matt Vess, U.S. Army (ret.).

Dateline New Haven with Paul Bass, WNHH Community Radio, January 2023.
Kica's Corner, WNHH Community Radio, with Chief Karl Jacobson (2022). https://www.youtube.com/watch?v=YyKxODiMYrI 

Dr. K (Alok Kanojia), "Why Giving Up Addiction Feels Impossible," HealthyGamerGG. https://www.youtube.com/watch?v=nsUz2Ysg1XU

Hamden Action Now, "Community Conversation: The Culture of Policing & The Randy Cox Incident" (2022).

Voicemail from my cousin Matt.

Posts from r/problemgambling, read as written.

SOURCES

The case against Karl Jacobson Connecticut Division of Criminal Justice, arrest announcement (Feb 20, 2026) https://portal.ct.gov/dcj/press-releases/division-of-criminal-justice/02202026newhavenpolicechief

Connecticut Division of Criminal Justice (Jan 6, 2026) https://portal.ct.gov/dcj/press-releases/division-of-criminal-justice/01062026newhaven 

New Haven Independent, "Arrest Warrant: Chief Bet $4.4M Online" (Feb 20, 2026) https://www.newhavenindependent.org/2026/02/20/arrest-warrant-chief-bet-4-4m-online/ 

CT Public (Feb 20, 2026) https://www.ctpublic.org/news/2026-02-20/new-haven-police-chief-arrest-embezzlement 

WTNH, "Former New Haven police chief arrested after admitting to taking city funds" (Feb 20, 2026) https://www.wtnh.com/news/connecticut/new-haven/former-new-haven-police-chief-arrested-after-admitting-to-taking-city-funds/amp/ 

WFSB (Mar 6, 2026) https://www.wfsb.com/2026/03/06/former-new-haven-police-chief-due-court-larceny-charges/ 

WTNH, "Former New Haven police chief appears in court in embezzlement case" (Aug 4, 2026) https://www.wtnh.com/news/connecticut/new-haven/former-new-haven-police-chief-due-in-court-tuesday-for-embezzlement-case/amp/ 

New Haven Independent, "Arrested Ex-Police Chief's Criminal Case Continued" (Aug 4, 2026) https://www.newhavenindependent.org/2026/08/04/arrested-ex-police-chiefs-criminal-case-continued/

The pension WFSB (Jan 14, 2026) https://www.wfsb.com/2026/01/14/former-new-haven-chief-who-officials-say-admitted-stealing-will-receive-124332-year-pension 

City of New Haven, Police & Fire Pension Fund minutes (Jan 29, 2026) https://www.newhavenct.gov/home/showpublisheddocument/28102/639080445788370000 

City of New Haven, Police & Fire Pension Fund minutes (Mar 26, 2026) https://www.newhavenct.gov/home/showpublisheddocument/28656/639132288782030000 

New Haven Independent via Patch, "Pension Board Rejects Ex-Police Chief's Disability Application" (Mar 26, 2026) https://patch.com/connecticut/newhaven/pension-board-rejects-ex-police-chief-s-disability-application

The chief's term and his successor New Haven Independent via Patch, "Jacobson Confirmed As Police Chief" (July 8, 2022) https://patch.com/connecticut/newhaven/jacobson-confirmed-police-chief 

New Haven Independent, Zannelli confirmed (May 4, 2026) https://www.newhavenindependent.org/2026/05/04/zannelli-confirmed-as-police-chief/ 

NBC Connecticut, "New Haven swears in new police chief" (May 5, 2026) https://www.nbcconnecticut.com/news/local/new-haven-swears-in-new-police-chief-as-former-faces-embezzlement-charges/3733016/?amp=1

Plea deals Missouri v. Frye, U.S. Supreme Court (2012): "ninety-four percent of state convictions are the result of guilty pleas" https://law.cornell.edu/supremecourt/text/10-444

Project Longevity The Justice Education Center https://www.justiceeducationcenter.org/initiatives/project-longevity/

"The Tell-Tale Heart" (1843), Edgar Allan Poe Society of Baltimore https://www.eapoe.org/WORKS/tales/thearta.htm
 
Aleksandr Solzhenitsyn, The Gulag Archipelago, The Solzhenitsyn Center https://www.solzhenitsyncenter.org/notable-quotations 

Sigmund Freud, "Mourning and Melancholia" (1917), Standard Edition, Vol. XIV https://ia903101.us.archive.org/29/items/FreudMourningAndMelancholia/Freud_MourningAndMelancholia_text.pdf

A century of sports and gambling National Baseball Hall of Fame, Kenesaw Mountain Landis and the Black Sox https://baseballhall.org/hall-of-famers/landis-kenesaw 

AP via PBS NewsHour, "Pete Rose, baseball phenom who was banned for gambling, dies at 83" (Sept 30, 2024) https://www.pbs.org/newshour/nation/pete-rose-baseball-phenom-who-was-banned-for-gambling-dies-at-83 

ESPN, "Pete Rose, 'Shoeless' Joe Jackson among players reinstated by MLB" (May 13, 2025) https://www.espn.com/mlb/story/_/id/45115659/pete-rose-shoeless-joe-jackson-players-reinstated-mlb 

JURIST, leagues sue New Jersey under PASPA (Aug 9, 2012) https://www.jurist.org/news/2012/08/college-and-pro-sports-leagues-sue-new-jersey-to-prevent-sports-gambling/ 

Sportico, on the leagues and PASPA https://www.sportico.com/law/analysis/2024/legalized-sports-betting-new-scandals-1234783460/ 

Murphy v. NCAA, U.S. Supreme Court (May 14, 2018) https://www.law.cornell.edu/supremecourt/text/16-476 

AP via Bangor Daily News, "Supreme Court makes sports betting a possibility nationwide" (May 14, 2018) https://bangordailynews.com/2018/05/14/news/supreme-court-makes-sports-betting-a-possibility-nationwide/ 

NBA, MGM Resorts becomes official gaming partner (July 31, 2018) https://www.wnba.com/news/mgm-resorts-international-becomes-official-gaming-partner-of-the-nba MLB.com, 

"MLB, MGM announce gaming partnership" (Nov 27, 2018) https://www.mlb.com/news/mlb-mgm-announce-gaming-partnership-c301163068 

AP via WSLS, "NFL inks sports bet deals with Caesars, FanDuel, DraftKings" (Apr 15, 2021) https://www.wsls.com/sports/2021/04/16/nfl-inks-sports-bet-deals-with-caesars-fanduel-draftkings/ 

American Gaming Association, State of the States 2020 (2019 handle) https://americangaming.org/resources/state-of-the-states-2020/ 

American Gaming Association, 2025 commercial gaming revenue (Feb 26, 2026) https://www.americangaming.org/new/commercial-gaming-revenue-hits-78-7-billion-in-2025-driving-record-18-1-billion-in-gaming-taxes-nationwide/

The integrity cases AP via WGCU, NFL gambling suspensions (June 29, 2023) https://news.wgcu.org/section/sports/2023-06-29/nfl-suspends-3-players-indefinitely-fourth-gets-6-games-for-violating-gambling-policy 

AP via FOX 9, Uwazurike suspended (July 24, 2023) https://www.fox9.com/news/nfl-suspends-broncos-eyioma-uwazurike-indefinitely-for-gambling-on-games 

NHL statement on Shane Pinto (Oct 26, 2023) https://media.nhl.com/site/vasset/public/attachments/2023/10/17365/Pinto102623.pdf 

A check for $1,000 and on the memo line... Toy Give Away.Another one for $3,000... Toy Drive. Both made out to the chief of police. Two days before Christmas.

If you'd like to support the show you can do so on Patreon or PayPal.

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

https://www.tapesfromthedarkside.com/paypa

On the floor of a New Haven holding cell, paralyzed, while the officer standing over him laughed and asked why he kept winking, Randy Cox said: "I need somebody to take me seriously."

It's on page 17 of a 70-page internal affairs report, no news outlet ever printed it, and it's the reason this episode exists.

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

Merch
https://merchfromthedarkside.com/

PayPal / Venmo for a one time donation
https://www.paypal.com/donate/?hosted_button_id=S73N9V6V3MC7L

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

Merch store relauch. Everything is on sale for a limited time.
https://merchfromthedarkside.com/

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.

Gambling ads have been appearing this season. I don't like that. Here's the situation.

***

Questions, comments, etc.
[email protected]

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.

Support us on Patreon:
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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.”

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Patreon:
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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!
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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