Tyler considers Winnie and Nelson: Portrait of a Marriage one of the best books of the last decade, and its author Jonny Steinberg one of the most underrated writers and thinkers—in North America, at least. Steinberg's particular genius lies in getting uncomfortably close to difficult truths through immersive research—spending 350 hours in police ride-alongs, years studying prison gangs and their century-old oral histories, following a Somali refugee's journey across East Africa—and then rendering what he finds with a novelist's emotional insight.

Tyler and Jonny discuss why South African police only feel comfortable responding to domestic violence calls, how to fix policing, the ghettoization of crime, how prison gangs regulate behavior through century-old rituals, how apartheid led to mass incarceration and how it manifested in prisons, why Nelson Mandela never really knew his wife Winnie and the many masks they each wore, what went wrong with the ANC, why the judiciary maintained its independence but not its quality, whether Tyler should buy land in Cape Town, the art scene in Johannesburg, how COVID gave statism a new lease on life, why the best South African novels may still be ahead, his forthcoming biography of Cecil Rhodes, why English families weren't foolish to move to Rhodesia in the 1920s, where to take an ideal two-week trip around South Africa, and more.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded September 29th, 2025.

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Timestamps:

• 00:00:40 – Policing and crime in South Africa
• 00:11:15 – Prison culture
• 00:22:04 – Nelson and Winnie Mandela's marriage
• 00:24:47 – Was Winnie Mandela just a bad person?
• 00:29:20 – Nelson Mandela's masks
• 00:32:04 – Mandela's legacy and the ANC
• 00:36:51 – Reasons for optimism in South Africa
• 00:50:58 – His forthcoming biography of Cecil Rhodes
• 00:55:15 – Where to visit in South Africa