🤫 #100 - Special Agent Jim DiOrio: Inside The Psychology Of A Legendary FBI Undercover Agent

(***TIMESTAMPS in Description Below) ~ Jim DiOrio is a Former FBI Interrogation Expert, Military Veteran, Undercover Operative, and Savage.

A member of West Point’s Class of 1986 (along with his roommate and former Secretary of State/Director of The CIA, Mike Pompeo), Jim served overseas as an Army Ranger in the late 80’s and early 90’s before leaving the military and joining the FBI. He went on to spend 10 years as one of the most successful undercover agents in the Bureau’s history––and another 15 as a ferocious Special Agent In-Charge and heralded FBI interrogator around the world. Basically, he was the guy who told Captain Phillips he could have his boat back. 

 

Currently, Jim is the CEO of J3 Global, an international crisis/security firm (or as he explains it: “I’m Ray Donovan with more experience”). In his spare time, he also owns a Jersey Mike’s because why not.

***TIMESTAMPS***

0:00 - Intro; Jim talks about getting in meditation; a funny story about Jim’s dog; Thinking of life “in sets”; Jim talks about how he wants to be viewed when he’s gone

21:14 - Jim analyzes his West Point classmate and friend, former Secretary of Defense Mark Esper’s, new book about his time working for the Trump Administration; Reacting to the “policy requests” Trump made during his Presidency

42:34 - How the Joint Chiefs of Staff and Defense Secretary positions work in the executive branch; Trump wanted to bail everybody out of South Korea and Esper disagreed; Why did Esper write the book now?; Endless Wars and debating military outreach in the US

1:01:10 - Why did Esper take job if he knew Trump was crazy?; The two sides of the debate over guys like Esper who comment on Trump; The moment Esper had had enough; Jim reflects on the cool guys at West Point; Jim explains Esper’s style and personality

1:20:38 - Jim goes through the backstory of his 9 year career as an Army Ranger; How the military gave Jim instantaneous rank at the FBI

1:34:32 - Jim discusses his own PTS and how he spots it in other people; “War is hell”; Survivor’s guilt; Jim tells a story about a time somebody pushed a woman in bar; Why Jim went into the ocean at dark

1:52:28 - Jim explains his Undercover career at the FBI; His previous undercover experience while in the military; Jim’s lifestyle while undercover; How Jim infiltrated groups undercover; “The ask” moment; Why bad guys always come back to chase the answer

2:19:02 - Jim expands upon his interrogation approaches; How Jim gets in people’s heads; How Jim’s fear of dismissal played a role in his skill as an interrogator; Taking interrogations home with you; Chip on shoulder vs boulder on shoulder; Understanding a criminal’s actions by understanding their childhood, environment, and background; empathy for criminals?

2:48:09 - Jim gives some of the details about his role in the mission to rescue Captain Phillips from Somali Pirates off the coast of Africa in April 2009; Jim discusses his role in the investigation of the 1996 TWA 800 plane crash

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YouTube EPISODES & CLIPS:

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