In his third appearance on Conversations with Tyler, Nate Silver looks back at past predictions, weighs how academic ideas such as expected utility theory fare in practice, and examines the world of sports through the lens of risk and prediction.

Tyler and Nate dive into expected utility theory and random Nash equilibria in poker, whether Silver's tell-reading abilities transfer to real-world situations like NBA games, why academic writing has disappointed him, his move from atheism to agnosticism, the meta-rationality of risk-taking, electoral systems and their flaws, 2028 presidential candidates, why he thinks superforecasters will continue to outperform AI for the next decade, why more athletes haven't come out as gay, redesigning the NBA, what mentors he needs now, the cultural and psychological peculiarities of Bay area intellectual communities, why Canada can't win a Stanley Cup, the politics of immigration in Europe and America, what he'll work on next, and more.

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

Recorded July 23rd, 2025.

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Annie Jacobsen has a favorite word for America's nuclear doctrine: madness. It's madness that any single person has six minutes to decide the fate of civilization, madness that we've built weapons capable of ending the world in 72 minutes, and madness that everything hangs by the thread of deterrence. But to Tyler, life is "a lot of different kinds of madness," and the real question is simply getting the least harmful form available to us. It's a conversation sparked by her latest book Nuclear War: A Scenario, which Tyler calls one of his favorites from last year—and which is compelling enough that Denis Villeneuve is turning it into a screenplay.

Tyler and Annie explore whether we should be more afraid of nuclear weapons or if fear itself raises the risks, who should advise presidents during the six-minute decision window, whether moving toward disarmament makes us safer or more vulnerable, what Thomas Schelling really meant about nuclear war and rational actors, the probability that America would retaliate after a nuclear attack, the chances of intercepting a single incoming ICBM, why missile defense systems can't replicate Israel's Iron Dome success, how Pakistan-India nuclear tensions could escalate, why she's surprised domestic drone attacks haven't happened yet, her reporting on JFK assassination mysteries and deathbed phone calls, her views on UFOs and the dark human experiments at Area 51, what motivates intelligence community operators, her encounters with Uri Geller and CIA psychic research, what she’s working on next, and more.

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

Recorded May 19th, 2025.

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Helen Castor is a British historian and BBC broadcaster who left Cambridge because she wanted to write narrative history focused on individuals rather than the analytical style typical of academia. As someone interested in individual psychology and the functioning of power, Castor finds medieval England offers the perfect setting because its sophisticated power structures exist in “bare bones” without the “great apparatus of state,” bringing individual power plays into sharper relief. Her latest book, The Eagle and the Hart, exemplifies this approach by examining Richard II and Henry IV as individuals whose personal choices became constitutional precedents that echo through English history.

Tyler and Helen explore what English government could and couldn't do in the 14th century, why landed nobles obeyed the king, why parliament chose to fund wars with France, whether England could have won the Hundred Years' War, the constitutional precedents set by Henry IV's deposition of Richard II, how Shakespeare's Richard II scandalized Elizabethan audiences, Richard's superb artistic taste versus Henry's lack, why Chaucer suddenly becomes possible in this period, whether Richard II's fatal trip to Ireland was like Captain Kirk beaming down to a hostile planet, how historians continue to discover new evidence about the period, how Shakespeare’s Henriad influences our historical understanding, Castor’s most successful work habits, what she finds fascinating about Asimov's I, Robot, the subject of her next book, and more.

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

Recorded April 2nd, 2025.

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Photo Credit: Stuart Simpson