“Dealing with Russia” – A Conversation with Counterintelligence Legend Jim Olson

Summary

Jim Olson (Website) joins Andrew (Twitter; LinkedIn) to discuss Putin and Russia. He had a 31-year career with the CIA including a tour in Moscow.

What You’ll Learn

Intelligence

• His views on Russia and its trajectory since the Cold War’s end
• His frank assessment of Putin and admiration for the Russian people
• His time in Moscow with 3 rotating KGB teams surveilling him
• His time as Chief of Station in the city of spies Vienna

Reflections

• A “beautiful marriage” with American technology 
• Passing the generational baton

And much, much more…

Episode Notes

“James Olson is a legend in the clandestine service,” not my description of this week’s guest, but that of former CIA Director and Secretary of Defense Robert Gates. Jim spent 31 years in the CIA, including tours in Moscow, Vienna & Mexico City, and rose to become Chief of CIA Counterintelligence. He is the author of Fair Play and To Catch a Spy. 

He joined Andrew to speak about Russia. He speaks the language, spent time living and working in the country, where he was involved in one particularly daring operation that he shares with us in the episode, and he faced off against the organization that would go on to become the current SVR and FSB – the KGB.

Jim has had Vladimir Putin on his radar for many a year, and he doesn’t pull any punches reflecting on his trajectory in this episode.

And…

Jim grew up in a small town in Iowa where, “we didn’t really follow international affairs, we joked among ourselves…if it didn’t affect the price of corn, we weren’t really interested.” My, how things changed for Jim.

Quote of the Week

"I have tremendous respect for the Russian people. They are long suffering. I've gotten to know many Russians. I've worked with a lot of Russians. I found them to be people who had a real soul. They had a human qualities that I could admire, but they were locked into a repressive regime that did not allow them to express any of those human sentiments that that they felt." – Jim Olson

Resources

Headline Resource

• To Catch a Spy: The Art of Counterintelligence, J. Olson (GUP, 2019)
• Fair Play: The Moral Dilemmas of Spying, J. Olson (Potomac, 2008)

*SpyCasts*

• “The Spymaster’s Prism” – with Jack Devine (2021)
• “Russians Among Us: The Hunt for Putin’s Spies” – with Gordon Corera (2020)
• “The Corrupted State” – with Ilya Zaslavskiy (2016)
• “Putin’s End Game in Ukraine” – with KGB General (Retd.) Oleg Kalugin (2014)

Beginner Resources

• To Catch A Spy with J. Olson, C-SPAN (2020) [9:44 minutes] 
• The Best Books on Counterintelligence, J. Olson, Shepherd (n.d.)
• Putin’s Revisionist History of Russia and Ukraine, I. Chotiner, New Yorker (2022)

Books

• Putin’s People, C. Belton (Picador, 2022)
• Operative in the Kremlin, F. Hill & C. Gaddy (Brookings, 2015)
• One Soldier’s War in Chechnya, A. Babchenko (Portobello, 2008)

Articles

• Former CIA Leader Said LinkedIn is Like a Candy Store to China, C. Burgess, ClearanceJobs (2022)
• New Documentary Series Explores Pollard Affair, H. Brown, Jerusalem Post (2022)
• J. Olson First Recipient of “The Spirit of Aggieland – 41 Award,” J. Adams, KAGS (2022)
• Ex-CIA Chief on Accused Chinese Spymaster, P. Christian, WCPO (2021)

Videos

• To Catch A Spy with J. Olson, Houston World Affairs Council (2020)

Primary Sources

• James Collins Oral History, US Ambassador to Soviet Union, 1997-2001 (n.d.)
• Jack Matlock Oral History, US Ambassador to Soviet Union, 1987-1991, (n.d.)
• Ukraine: Memo. On Security Assurances (1994)
• Belovezha Accords, Eyewitness Account of Former Belarus Soviet Leader (1991)

*Wildcard Resource*

• What Classic Russian Literature Can Teach us about Putin’s War on Ukraine 
• Putin is a big fan of Dostoevsky – who underwent a mock execution & four years of hard labor in Siberia for belonging to a literary discussion group feared by the Tsarist autocracy. 

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