As a Westerner who has lived in Singapore--and once found himself under the suspicions of the police--this book had a particular relevance for me. Living in Singapore, you agree to the social pact--and you know deviating from this pact can have dire consequences, literally.
And for most people living in Singapore this works out swimmingly--you sacrifice some personal liberties (recreational drug use, political dissent, chewing gum) for a living standard that is among the best in the world; a clean, safe, well-managed, stylish metropolis.
0f course, if you disrupt this harmonious city, you will be punished. While I was living there, a Swiss national Fricker was caned for graffiting a train car. Singapore's incarceration rate is second highest in the world, trailing only the US. And capital and corporal punishment, if not common, is certainly not uncommon.
0nce a Jolly Hangman details the cases of a dozen people who have committed crimes that were eligible for the death penalty. Each chapter presents a different case, making the book feel more like a collection of essays than a cohesive book (although it makes for easy start-and-stop reading). The cases cover a range of people, from Filipino maids to rich Western expats.
No one should be surprised that wealthy, connected people receive the death penalty less than their poor counterparts (then again, maybe only no Americans should be surprised--it the US, capital punishment is reserved primarily for poor, dumb blacks).
Shadrake is a journalist by trade, and the book reads more like a long magazine article than a scholarly work. The interviews with the executioner himself (in his HDB in Woodlands?!?) was my favorite bit--it added a human element to the executions. And I found the history of the Singapore prison system compelling as well.
The book falls short in explaining why Singapore has such draconian punishments (like why chewing gum is banned or graffiti is so harshly treated), anecdotes that would lend balance. The author is unabashedly against the death penalty, but doesn't place this view in the context of how Singapore developed its positions. I don't agree with many policies in Singapore, but I at least attempt to understand their reasoning.
That said, highly recommended if you're living in Singapore or have an interest in capital punishment.