Generation Jihad

Latest Episodes:

Ceasefire or Long Game? Apr 09, 2026

Show notes

FDD Senior Fellow David Daoud and Bill examine the recent and fragile ceasefire in the ongoing Iran War. Will the fighting in southern Lebanon between Israel and Hezbollah break the peace, and has the Iranian resistance movement missed a golden opportunity?

Risky Raid Behind Enemy Lines Apr 06, 2026

Show notes

Bill and FDD Senior Analyst, Cameron McMillan, unravel the complex rescue of two US airmen shot down over Iran - including the strategic coordination and risks involved with the operation - as well as the current state of the Iranian ballistic missile program, and Tehran’s strategic adaptability amidst the dynamic conditions of this war.

Timeline after Timeline Apr 02, 2026

Show notes

FDD’s Janatan Sayeh is back with Bill for an update on the Iran war, including: the potential for concrete regime change, last night’s address by President Trump, rumored U.S.-Iran deliberations, the fragile balance of power on the ground, and the possibility of a popular uprising against the wounded Islamic Republic.

Tehran's proxies have entered the chat Mar 31, 2026

Show notes

As U.S. and Israeli strikes hit inside Iran, the regime is firing back outside its borders — and the war is expanding because of it. Iraqi militias target U.S. forces. The Gulf is under attack. The Houthis are back in the fight. This isn’t spillover — it’s strategy.

Ahmad Sharawi and Bridget Toomey are back with Bill to assess Iran’s expanding proxy war — and the growing risk that America is funding forces now targeting its own troops.

The Kharg Island Trap Mar 27, 2026

Show notes

Kharg Island looks like the perfect target — take it, and you choke off Iran’s oil. But it’s not that simple.

Bill is joined by Ryan Brobst and Cameron McMillan to discuss why seizing Kharg could hand Tehran exactly what it wants: a wider war, a vulnerable U.S. position, and a fight on the regime’s terms.

The Hormuz Shake(down) Mar 25, 2026

Show notes

Iran says the Strait of Hormuz is closed. It’s not.

Ships are still moving. Oil is still flowing.

Just not for everyone. Friends pass. Also anyone with millions of dollars to spare.

Enemies don’t.

This isn’t a blockade. It's a shakedown.

Bill Roggio sits down with shipping expert Sal Mercogliano to break down Tehran’s latest act of war: turning the world’s most critical shipping chokepoint into leverage.

The regime falls when the people rise Mar 23, 2026

Show notes

The bombs are falling. The regime is reeling. But revolutions aren’t won from 30,000 feet.

As Washington and Jerusalem pummel toward a mission accomplished, Bill is joined by FDD's Jon Schanzer to grapple with a harder question that looms: what happens if there’s no uprising when the bombing stops?

Games Without Frontiers Mar 19, 2026

Show notes

As pressure builds inside Iran, the regime is lashing out across the region.

Bill Roggio, Joe Truzman, and David Daoud break down Tehran’s expanding battlefield from internal strain to external escalation and the question at the center of it all: Is this strength or a regime under stress trying to change the game before it loses control?

Mentioned by Bill

We didn't light it, but we tried to fight it.

Day 14 of the Iran War

Don't want the regime to have nukes? Eliminate the regime.

When the most stable place in the Middle East is Syria... Mar 16, 2026

Show notes

As the US and Israel strike targets inside Iran’s borders, the regime is firing back outside of them.

Across the region from tourist hubs and capital cities to energy infrastructure and U.S. military bases, Iranian attacks are dragging the region into the war and raising the cost of conflict.

Ahmad Sharawi joins Bill to assess Tehran’s strategy and the threat it poses to Middle East stability — including a nightmare maritime scenario that no one is talking about.

Day 14 of the Iran War Mar 13, 2026

Show notes

As U.S. and Israeli strikes pound Iran’s military and Tehran threatens shipping in the Strait of Hormuz, the conflict is entering a dangerous new phase.

FDD’s Bradley Bowman joins Bill to break down what the strikes have achieved — and the harder question that remains: is the goal to weaken the regime… or bring it down?

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