Stan McChrystal has spent a long career considering questions of risk, leadership, and the role of America’s military, having risen through the Army’s ranks ultimately to take command of all US and NATO forces in Afghanistan, a force representing 150,000 troops from 45 countries. Retiring as a four-star general in 2010, he has gone on to lecture at Yale and launched the McChrystal Group, where he taps that experience to help organizations build stronger teams and devise winning strategies. His latest book, which he tells Tyler will be his last, is called Risk: A User’s Guide. He joined Tyler to discuss whether we’ve gotten better or worse at analyzing risk, the dangerous urge among policymakers to oversimplify the past, why being a good military commander is about more than winning battlefield victories, why we’re underestimating the risk that China will invade Taiwan, how to maintain a long view of history, what set Henry Kissinger apart, the usefulness of war games, how well we understand China and Russia, why there haven’t been any major attacks on US soil since 9/11, the danger of a “soldier class” in America, his take on wokeness and the military, what’s needed to have women as truly senior commanders in the armed forces, why officers with bad experiences should still be considered for promotion, how to address extremists in the military, why he supports a draft, the most interesting class he took at West Point, how to care for disabled veterans, his advice to enlisted soldiers on writing a will, the most emotionally difficult part and greatest joys of his military career, the prospect of drone assassinations, what he eats for his only meal of the day, why he’s done writing books, and more. Visit our website: https://conversationswithtyler.com Email: [email protected] Follow us on Twitter: https://twitter.com/cowenconvos Follow us on Instagram: https://instagram.com/cowenconvos/ Follow Tyler on Twitter: https://twitter.com/tylercowen Follow Stanley on Twitter: https://twitter.com/StanMcChrystal Like us on Facebook: https://facebook.com/cowenconvos Subscribe to our Newsletter: https://go.mercatus.org/l/278272/2017-09-19/g4ms Thumbnail photo credit: Leading Authorities, Inc.