SpyCast 4.5.22
Ep 533 | 4.5.22

"ISIS Leader al-Mawla: Caliph. Scholar. Canary. Snitch." – with Daniel Milton, West Point CTC Director (Part 1 of 2)

Show Notes


Daniel Milton (Website; Twitter) joins Andrew (Twitter; LinkedIn) to discuss Tactical Interrogation Reports of the former Caliph of the Islamic State. Al-Mawla was killed in a U.S. raid in February 2022. 

What You’ll Learn


  • The ideological feud between Islamic State and Al Qaeda 
  • Islamic State's retreat from a quasi-state centered to a shadowy insurgency
  • Battlefield intelligence such as “exploitable material” and “interrogation reports”
  • The role of the Combating Terrorism Center in analyzing this intelligence


  • Training your people for the current fight…and the next one 
  • The trade-off between a short-term view and a longer-term view

And much, much more…

Episode Notes

This week’s episode focuses on battlefield intelligence, or more specifically a series of tactical interrogation reports from 2008. 

Ok, so why are they significant? Well, the individual being interrogated, Al Mawla, would go on to become the second leader and so-called Caliph of the Islamic State. Ok, so why are they significant beyond that…well, it turns out that Al Mawla was an informant who gave away colleagues and friends to save his own skin, leading to the nickname, “The Canary Caliph.”

Daniel Milton joined Andrew to discuss these reports and what they mean in the broader scheme of things. Daniel is the Director of Research at the Combatting Terrorism Center at West Point, and he has a Ph.D. from FSU. He has been cited in outlets such as The NYT, BBC, and NBC News and he regularly briefs all levels of the Government, including the Intelligence Community and Department of Defense.


In February 2022, Al Mawla became the second Islamic State Caliph to blow himself up during a U.S. raid. His predecessor Abu-Bakr al-Baghdadi had done so in October 2019. I wonder what will happen to the third Caliph…

Quote of the Week

"I think that's one of my favorite things about looking at this type of material is that it really gives an inside view to organizations that are clandestine and usually not seen very well from the outside, but these documents paint a very vivid picture of struggles, challenges, bureaucratic minutia, whatever the case might be, which is not typically how we think about these organizations, but these documents really allow us to see that." – Daniel Milton


*Headline Resources*


  • Enemies Near & Far, D. Gartenstein-Ross (CUP, 2022)
  • The ISIS Reader, Ingram et al. (Hurst, 2020)
  • The Rise of Global Jihad, T. Hegghammer (CUP, 2020)
  • Foreign Fighters in the Armies of Jihad, D. Byman (OUP, 2019)
  • Anatomy of Terror, A. Soufan (W.W. Norton, 2017)
  • The Far Enemy, F. Gerges (CUP, 2005)
  • Best Books on the Middle East (Five Books)




  • Operation Inherent Resolve

Primary Sources

Wildcard Resource