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History’s Worst Decisions

History’s Worst Decisions

And the People Who Made Them

Author:Stephen Weir
Category:History
Publisher:Metro Books
Published:September 9, 2026
ISBN:9781435111745
Language:English
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Description:

TL;DR

5/10. Fifty historical disasters from the Trojan War to Enron, arranged by the motive behind each one. Entertaining, briskly written, and not reliable enough to cite. Treat it as a list of things to go and read about properly.

Weir runs from Adam and Eve through Hannibal crossing the Alps, Nero, Erik the Red selling Greenland on its name, Moctezuma, Lord North and the tea, the Dutch trading Manhattan for a nutmeg island, the Maginot Line, Gallipoli, thalidomide, Robert Maxwell, and Enron.

Fifty entries, each a few pages, each with a named culprit and a stated motive drawn from a fixed list: anger, greed, pride, sloth, lust, false hope, faith.

It was originally published as Encyclopedia Idiotica in 2005 and reissued under this title, which tells you the register it was written in.

What does History’s Worst Decisions get right?

The organising device, which is genuinely good and which I would steal.

Sorting failures by motive instead of by period puts Moctezuma next to Enron and makes you notice that they rhyme. Pride operates the same way in a palace and a boardroom. False hope produces the same behavior in a fourteenth-century pope hunting for Prester John and in a twentieth-century executive who cannot admit a division is losing money.

That is a real insight about human decision-making and it is buried in a book that does not develop it.

The range is also good. Military, corporate, diplomatic, engineering, and religious failures in one place, which most books on this subject do not attempt because they are usually written by a specialist in one of those fields.

How reliable is the history?

Not reliable enough to cite, and this is the problem the book cannot recover from.

Readers who know the individual periods have found errors throughout, ranging from small factual details a search would have caught to premises whole chapters rest on. That is a serious charge and it is the consistent finding of people qualified to check.

Several entries are not decisions at all. They are famous disasters, which is a different thing. A tsunami is not a bad decision, and including it because it is well known undermines a book whose entire premise is the decision.

At least one entry presents a conspiracy theory as established. In a book about how people convince themselves of things that are not true, that is more than an error, it is a failure of the book’s own argument.

What does History’s Worst Decisions miss?

Why the decisions were made, which was the whole opportunity.

A book on this subject should be mostly about the reasoning that produced the disaster: what the person knew, what they believed, what pressure they were under, and why the wrong choice looked right from inside. That is where the value is, because that is the part a reader can apply.

This book is mostly about the disaster, which the reader already knows. Weir names a motive and moves on, and a motive is not an explanation. Saying that Gallipoli happened because of pride does not tell you anything about how a competent government approved a plan that bad.

Compare it to what Gawande does with medical error or what Kahneman does with judgment, and the gap is obvious. Those books are about the mechanism. This one is about the wreckage.

Is History’s Worst Decisions worth your time?

As a source of leads, yes. Several entries sent me looking for better books on the same events, and a few of those became genuinely useful.

The Maginot Line, the Dutch and Manhattan, and the thalidomide story are all worth chasing properly, and this book is a serviceable index to them.

Nothing in it should be repeated without checking somewhere else first, which is an awkward thing to say about a work of nonfiction and is the honest position.

Verdict

Read it as a source of leads, not as history. The motive-based structure is worth stealing, several entries will send you to better books, and nothing in it should be repeated without verification.

I am harder on it than most readers because a book with this title had a real opportunity and did not take it. The interesting question was why, and the book answers what.

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Frequently Asked Questions

What is History’s Worst Decisions about?
Fifty historical disasters from the Trojan War through Gallipoli, thalidomide, and Enron, each attributed to a named culprit and a stated motive such as pride, greed, or false hope. It was first published as Encyclopedia Idiotica in 2005.
Is History’s Worst Decisions historically accurate?
Not reliably. Readers who know the periods have found errors throughout, from small factual details to premises whole chapters rest on. Several entries are famous disasters instead of decisions, and at least one presents a conspiracy theory as established.
What is the best thing about History’s Worst Decisions?
The organising device. Sorting failures by motive instead of chronology puts Moctezuma next to Enron and makes the rhyme visible, which is a real insight about decision-making, though the book does not develop it.
What does History’s Worst Decisions miss?
The reasoning that produced each disaster: what the person knew, what they believed, what pressure they were under, and why the wrong choice looked right from inside. Naming a motive is not an explanation.
How does History’s Worst Decisions compare to better books on failure?
Poorly. Gawande on medical error and Kahneman on judgment are about the mechanism. This book is about the wreckage, which the reader already knows.
Which entries are worth chasing?
The Maginot Line, the Dutch trading Manhattan, and the thalidomide story are all worth reading about properly elsewhere, and this book works as a serviceable index to them.
Should you read History’s Worst Decisions?
As a source of leads, yes. Nothing in it should be repeated without checking somewhere else first, which is an awkward thing to say about a work of nonfiction and is the honest position.
Why the low score?
Because a book with this title had a real opportunity and did not take it. The interesting question was why people decide badly, and the book answers what happened instead.

About the author

Stephen Weir

Stephen Weir is a British writer, editor, and publisher, educated at Cambridge University, who has worked on three continents across a career in publishing. His professional background is unusual for a popular history author in that much of it was spent on the other side of the desk. He has worked with authors including the Australian novelist Patrick White, who…

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