Iraq, Afghanistan, ISIS, & Ukraine: One Fighter’s Journey Through Modern War | Ryan O'Leary | Ep. 409

Ryan O'Leary, a U.S. Army National Guard veteran from Iowa, recounts his transformative journey through some of the most intense and complex conflicts of the 21st century—Iraq, Afghanistan, northern Iraq during the ISIS crisis, and Ukraine. His service began in 2004 with deployments to Iraq and Afghanistan, where he experienced the shift from static base security to dynamic infantry combat. After leaving the Guard in 2014, he joined the Peshmerga and later fought with Iranian Kurdish militias, witnessing the ideological evolution from separatism to democratic confederalism and the devastating consequences of Western inaction in supporting these groups. In 2022, he crossed into Ukraine as a foreign volunteer, enduring chaotic early defenses of Kyiv, brutal combat in Moshoon, and near-fatal ambushes in Irpin. Despite command failures and inadequate support, his unit adapted through improvisation, drone warfare, and high-speed assaults, eventually forming a specialized drone operations unit in Kyiv. However, strategic mismanagement led to the unit’s disbandment in 2025, prompting O'Leary to establish a European advisory group focused on drone tactics, counter-drone strategies, and the future of asymmetric warfare. Throughout his narrative, he emphasizes the human cost of war, the resilience of local fighters, and the moral imperative to dismantle the Russian military as a criminal enterprise, while drawing a clear line between coerced conscripts and mercenary-like forces who willingly commit atrocities.