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.

https://www.patreon.com/tapesfromthedarkside

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