Deep Cover Deep Cover

My Oldest, Dearest Friend

Jun 22, 2026 · 27m

Summary

Host Jake Halpern interviews Mike Walton, the oldest friend of bank robber Keith Giamonco, to explore their lifelong bond and Keith’s hidden criminal life. Mike recounts small, overlooked clues, like Keith borrowing money while claiming to day trade, which now seem like omens of the crimes. The episode examines male stoicism, questioning why deep intimacy often fails to reveal a friend’s true struggles or secrets.

Topics discussed

Sponsor ads: Navy Federal, Samsung, and ChatGPT Work Introduction: Keith's oldest friend Mike Walton Childhood memories and Mike's career as a car salesman Reflections on male friendship and stoicism Sponsor ads: SimpliSafe, ChatGPT, and Samsung Mike's shock at Keith's arrest and the 'day trading' cover Mike's confusion over Keith's motives and lack of remorse Mike's loyalty and the nature of long-term friendship Credits and final sponsor messages
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