Doomed to Fail

By Taylor Pineiro, Farz SokhansanjComedy True Crime History

Doomed to Fail episodes

February 16 Ep 237: Real Life Super-Villain? - Carlos the Jackal
When does someone turn into a super villain? Let's talk about Carlos the Jackal - part serial killer, part terrorist, full guy who just wants to make a mess.

We'll walk through his childhood in South America and his adulthood in literally any organization that needed a murderer.
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52 min
February 15 Re-Release: Lucy Letby - Who would harm a baby?
Netflix just released 'The Investigation of Lucy Letby' so let's re-relase our episode on this horrible story!
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44 min
February 13 Re-Release: Berlin 1936 - The Olympics under the Third Reich
In 1936, the Olympics were hosted in Berlin, Germany. You guessed it - things were not great.

We'll talk about the wonderfully talented American Jesse Owens, the invention of Basketball, and the propaganda of Leni Riefenstahl. It was a scary time to be in Europe - Hitler thought that every Olympics would be in Berlin for the rest of time, but they did not.

The basketball courts would later be hanging fields.
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59 min
February 09 Ep 236: A Stolen Ship to Freedom - Robert Smalls

It's Black History Month! Today, we're talking about Robert Smalls. Smalls was born enslaved, worked on ships for the confederacy whilst enslaved, and then took it upon himself to steal a steam ship, save his family & others, sail past Ft Sumter in the middle of the night, and provide the Union with guns & info.

Later, he went back south, invested in his community, and represented them in Congress.

Join us for this heroic tale!
Some sources:
https://www.battlefields.org/learn/primary-sources/robert-smalls-bold-feat-so-skillfully
https://www.pbs.org/wnet/african-americans-many-rivers-to-cross/history/which-slave-sailed-himself-to-freedom/
https://history.house.gov/People/Detail/21764
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39 min
February 06 Re-Release: The Ancient History of the Modern Olympics
Here we go! Happy Olympics 2026! Let's re-visit our episode where we went over how it started in Ancient Greece, & how it got to be a modern event!

Greece still gets special bonus treatment in the Olympics! They get to go out first & they get special access for tickets. Good for them.
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44 min
February 02 Ep 235: Fallacies of logic - Second Order Thinking with Juan Carlos Pineiro
Today we have a guest!! Juan Carlos Pineiro - the creator of the Re:Mind Mental Model set (and also Taylor's husband) is here to walk us through three examples of doomed scenarios that used 'Second Order Thinking' to the detriment of many! Second Order Thinking is only thinking about immediate consequences and not thinking in the long term.

Like when the city of Cleveland released millions of balloons into the air in 1986, the cultural treasure that is the Biosphere 2, and when doctors set out to give vaccines to people who hadn't had them before.

Three stories of things that did NOT work as expected!

Learn more about the Re:Mind card deck at https://remind.coach/ and follow Juan Carlos in Instagram @readjuancarlos - https://www.instagram.com/readjuancarlos/
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1 hr 14 min
January 27 Ep 234: 911 - From Switchboards to Text Messages, what's your emergency?
Let's talk the invention of 911 (that's 999 or 0118 999 881 999 119 725 3 if you're British). Did you know it wasn't full adopted in the US until the 2000s?? We'll go over AT&T, telephone lines, and switchboards!

You'll also hear Taylor list every time she's called 911 - feel free to share your 911 stories with us!
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32 min
January 20 Ep 233: FBI files - Crypto scams, family annihilators, and Olympic cartels
Today (amongst Heated rivalry chatter), we're talking the FBI's most wanted! The list, which is more publicity than anything, was started by who else but J. Edgar Hoover! We highlight three current fugatives who go in and out of the top ten.
Crypto Queen Ruja Ignatova ran a scam called OneCoin - then she boarded a RyanAir flight and disappeared!
Crappy husband Robert William Fisher murdered his family in Scottsdale, AZ - he then blew up the house and escaped into a national forest (we're hoping he's dead in a cave somewhere).
And! Canadian Olympic Snowboarder Ryan James Wedding went from competing on the slopes to running Mexico's biggest cartel. He's scary.
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38 min
January 12 Ep 232: We remember you! - Pluto (formerly the planet)
Let's talk about space!! We do have small panic attacks thinking about how Jupiter is huge and always raining. But, we're focusing on the little guy - Pluto! We'll talk about when he was discovered, who he was named after, and how he got demoted.

"Pluto is a planet" - Jerry Smith
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35 min
January 05 Ep 231: Wash your hands! - Typhoid Mary
Hello and welcome to 2026! Let's start it out with the story of Mary Mallon, who spread Typhoid Fever around NYC in the early 1900s. For a while, Mary didn't know that she was a 'healthy carrier' of the disease. But something started happening - every place Mary worked, people got sick. She was eventually 'caught' by investigator George Soper, quarantined, let go, started cooking AGAIN, and finally quarantined for life.

Wash your hands and join us!
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32 min

About Doomed to Fail

From the publisher's feed

We bring you stories of history's most notorious disasters and epic failures. Join us as we analyze the red flags and ask the important questions. How did things go so wrong? Could these disasters have been avoided?