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

Combat veteran Ryan O'Leary joins us to discuss his journey from the Army National Guard to fighting alongside Kurdish forces against ISIS in Iraq, working with Iranian Kurdish insurgent groups, and later experiencing the war in Ukraine firsthand. Ryan breaks down the realities of insurgency warfare, Kurdish resistance movements, and why modern conflicts are being transformed by drones, surveillance, and battlefield transparency.
This episode also dives into the future of warfare, the limits of regime change, corruption inside war zones, and what Western militaries still fail to understand about modern combat.

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00:00 — Start
01:25 — Growing up in Iowa and joining the Army National Guard
03:25 — Iraq deployment: FOB security and disillusionment with the war
04:20 — Afghanistan in RC Pactia: first firefights and combat patrols
05:45 — Ambushed on day one and surviving RPG attacks
08:50 — Why Afghanistan felt minor compared to later wars in Kurdistan and Ukraine
09:35 — Going AWOL to fight ISIS with the Kurds in Iraq
11:40 — Watching U.S. airstrikes outside Erbil as ISIS closed in
13:20 — Joining the Peshmerga with almost no process or paperwork
15:00 — Fighting across Iraq with Kurdish and Iranian Kurdish units
16:20 — The Kurdish-Iraqi civil war around Kirkuk explained
18:40 — Taking tank fire from Iraqi Abrams tanks during the fighting
21:10 — Mortar teams, ATGMs, and chaos on the Kirkuk front
24:00 — Kurdish independence, Kirkuk oil, and Iran’s role in the conflict
27:00 — U.S. weapons ending up with Iranian-backed militias and PMUs
29:00 — Meeting Iranian Kurdish fighters and deciding to work with them
32:10 — Living in the Qandil Mountains with Kurdish insurgents
34:20 — Kurdish separatism, Mahabad, and dreams of independence
39:10 — Life with Iranian Kurds: morale, culture, and surviving in the mountains
41:45 — Learning insurgency warfare from the inside
43:20 — Why insurgencies are nearly impossible to defeat
47:55 — Could Iranian Kurds actually help overthrow Tehran?
53:20 — Why regime change in Iran was always unrealistic
01:02:00 — Early Ukraine war experiences and how drones changed everything
01:14:30 — FPV drones, trench warfare, and why modern combat is now transparent
01:28:00 — What Western militaries still don’t understand about drone warfare
01:40:30 — Surviving artillery, drone drops, and constant surveillance in Ukraine
01:55:00 — Why infantry movement is becoming nearly impossible on the modern battlefield
02:07:00 — Foreign fighters in Ukraine: motivations, strengths, and problems
02:18:00 — Corruption, logistics, and the reality behind the Ukrainian war effort
02:31:00 — Lessons from Iraq, Kurdistan, and Ukraine for future U.S. wars
02:42:30 — China, Taiwan, and how drones could reshape the Pacific battlefield
02:54:00 — Why small units and adaptability matter more than ever
03:05:00 — The psychological toll of nonstop drone surveillance and attrition warfare
03:15:30 — Final thoughts on the future of warfare and where conflict is heading

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