The Jordan Harbinger Show 1243: Christopher Whitcomb | A Life Among Spies Part Two
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Nov 20, 2025 
Former FBI sniper Christopher Whitcomb shares harrowing tales from the front lines of covert intelligence work. He reveals the brutal reality of Guantanamo Bay and discusses the chaos of East Timor, where natural resources clashed with violence. Whitcomb reflects on the psychological toll of elite operators and the addictive nature of high-stakes missions. He also explores the complex relationship between private money and intelligence operations and offers insights into ongoing investigations and his upcoming books.
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Starting A Security Company In East Timor
- Christopher Whitcomb went to East Timor after Somalia seeking a “manageable” war and started a security company during civil unrest.
- He hired locals, paid payrolls in pallets of US dollars, and ran cash-heavy operations amid chaos and counterfeit currency.
Resource Wealth Breeds Chaotic Opportunity
- East Timor combined massive natural resources with extreme violence and weak governance, creating a Wild-West economy.
- That mix attracts contractors and foreign actors who can exploit resource wealth amid chaos.
Paying Payrolls In Millions Of Dollars
- Whitcomb described running payrolls in cash, sometimes withdrawing $2.5 million in twenties to pay thousands of local hires.
- Operating without banking infrastructure forced him to maintain armed contingents to deter violent payroll disputes.
