The Rest Is Classified – Episode 111: "The Man Behind The CIA: Shooting In The White House (Ep 2)"

Date: December 24, 2025
Hosts: David McCloskey (former CIA analyst, spy novelist), Gordon Corera (veteran security correspondent)
Main Theme:
An engaging, in-depth exploration of the legendary “Wild Bill” Donovan – founder of the Office of Strategic Services (OSS), forerunner to the CIA – focusing on his exploits during WWII, the creation and culture of the OSS, and the bureaucratic battles that led to the modern CIA. The episode vividly recounts Donovan’s bold personality, reckless leadership style, legendary antics, and the enduring mythos he fostered, all while examining how his legacy continues to shape the intelligence community.

1. Opening: Character Portrait & Context ([03:31]–[05:16])

• The episode kicks off with a colorful, almost mythic character sketch of Wild Bill Donovan, as described by Walter Lord:
  "Like some all potent oriental swami, he would with a wave of a hand, dispense justice to all within his orbit... Brilliant, energetic, imaginative and resourceful, he was unfortunately also selfish, petty, extravagant and something of a racketeer."
  — Read by David ([03:31])
• Hosts joke about the description fitting McCloskey, blending humor with reverence for Donovan’s eccentric leadership style.
• Recap of previous episode: how Donovan became key figure for FDR after Pearl Harbor, and his early clashes with J. Edgar Hoover.

2. The Birth of American Centralized Intelligence ([06:25]–[09:43])

The Post-Pearl Harbor Call

• After Pearl Harbor, Donovan is urgently summoned by FDR to Washington.
• FDR immediately asks: “Were the Nazis in on Pearl Harbor?” ([06:25])
• The importance: America’s intelligence failure spawns the need for centralized intelligence briefings (“the ancestor to the President’s Daily Brief”).
• Gordon highlights the novelty: “Feels like the first time you get the President being briefed on a daily basis.” ([07:11])

OSS Is Born

• Donovan leverages this trust to propose expanded intelligence and sabotage operations—transforming from info-gathering to clandestine action.
• The creation of the OSS in June 1942:
  “It’s a great title... Classic intelligence agency title, isn’t it? Grand, but doesn’t really tell you what they do. ‘Strategic Services’. I mean, what does that even mean?”
  — Gordon ([08:39])
• Hosts lampoon the opaque bureaucratic naming conventions (e.g., “Office of Technological Resources and Support”).

3. Wild Recruitment: The “Glorious Amateurs” of OSS ([10:50]–[13:27])

• Donovan’s rule-breaking approach:
  “I’d rather have a young lieutenant with guts enough to disobey an order than a colonel too regimented to think and act for himself.”
  — Quoted by David ([11:46])
• OSS recruitment is a mix of social elites (“oh, so social”), Ivy League professors, misfits, safecrackers, and those rejected by the military for “bad eyesight” (“the Bad Eyes Brigade”).
• Gender diversity: 35% of OSS were women—a surprisingly progressive stat for the era.
• Notables:
  • Julia Child (future chef), John Ford (Hollywood director), Alan Dulles, Richard Helms, William Colby, William Casey (future CIA directors).

4. OSS in Action: Chaos and Creativity ([13:54]–[16:04])

• Multiple operational divisions:
  • Secret intelligence
  • Analysis/research
  • Paramilitary (“mini McCloskeys,” commando groups)
  • Sabotage and “morale operations” (including wild schemes like exposing Hitler to “an insane quantity of pornography to incapacitate him”)
  • Black propaganda, psychological warfare, espionage
• Often reckless, frequently chaotic:
  • Anecdotes of failed or bizarre missions—e.g., briefcase lost to Gestapo, commandos dropped into neutral Sweden by mistake.

5. The Anglo-American Intelligence Relationship & Claridge’s Lore ([16:04]–[19:39])

• OSS’s London Station became its “beating heart”—almost 3,000 staff (25% of OSS).
• Espionage social life: parties, martinis, and sprawling Claridge’s suites.
• Hosts weave in personal anecdotes about their own first meeting at Claridge’s, humorously paralleling Donovan’s Anglophile habits.
• Tensions between the Brits and Americans:
  “Be careful what you wish for in your influence operations...”
  — David ([19:39])
• OSS’s reputation as “playing cowboys and Indians,” frustrating careful British SOE/MI6 planning.

6. Donovan’s Bravado: Guns in the White House and D-Day ([20:06]–[27:40])

• Daring exploits and dangerous showmanship:
  • Demonstrates a silenced pistol by firing it ten times into a sandbag in the White House to impress FDR.
    • “He’s literally shooting guns in the White House.” — Gordon ([22:03])
    • FDR is delighted, keeps the silencer; it’s displayed in the presidential library ([22:06])
  • Ignores orders and finagles his way onto a D-Day landing craft.
    • Absurdity of America’s top spymaster on the beach, ducking bullets, prepared to use cyanide L-pills (but left them at Claridge’s).
    • Gallows humor: “If we’re about to be captured, I’ll shoot you first. After all, I’m your commanding officer.” — Donovan, via Gordon ([26:34])
  • David reflects: “There was zero logic to doing any of this, but it makes for a great story and adds to the lore.” ([26:45])

7. The OSS Bureaucratic Aftermath: Power Struggles in Washington ([31:18]–[36:08])

• End of WWII brings existential questions for OSS.
• Donovan proposes in 1944 a permanent civilian intelligence agency (“Donovan Plan”).
• Violent opposition:
  • J. Edgar Hoover and the FBI fiercely resist—accusing OSS of being full of Communists and “virtually owned by the Brits.”
  • Pentagon/military also resist, especially Douglas MacArthur (longstanding rivalry).
  • Press leaks accuse Donovan of plotting an “American Gestapo.”
  • Donovan’s influence depended on personal rapport with FDR; after FDR’s death, he’s politically isolated.
  • Truman—distrustful of both Donovan and Hoover—dissolves OSS via Executive Order (September 20, 1945).

8. Donovan’s Sunset: Exile, Hope, and Legacy ([38:12]–[41:41])

• Donovan is exiled to legal/private life, briefly assistant prosecutor at Nuremberg Trials, later U.S. ambassador to Thailand.
• Despite hope of returning as CIA Director (campaigning for Eisenhower’s election), is bypassed in favor of Alan Dulles.
• Late years marked by declining health and dementia, reliving the glory days, “walking down the street in his pajamas to confront the invading Red Army.” ([40:19])
• When he dies, CIA cables worldwide:
  “The man more responsible than any other for the existence of the Central Intelligence Agency has passed away.” ([41:41])

9. Lasting Impact and Host Reflections ([41:41]–[48:21])

• Debate on OSS’s wartime effectiveness:
  • “Howling success? Maybe not. But the morale, myth, and momentum endured.”
  • McCloskey: “The legacy that Donovan and the OSS created, and really bequeathed to the early CIA as it’s developing... built around the personality of Wild Bill Donovan.” ([42:45])
• Key Differences: OSS/CIA as “tip of the spear” (paramilitary structure) vs. intelligence collection focus of MI6.
• Enduring tensions: CIA–FBI rivalries, British influence, bureaucratic warfare.
• Thoughts on leadership: Could another “Donovan” shape an agency in today’s world? Likely not—modern intelligence is too bureaucratized.
• The CIA’s own “tip of the spear” ethos and the statue of Donovan at Langley as his symbolic inheritance.

10. Notable Quotes & Memorable Moments

• On OSS recruitment:
  “OSS was said to stand for, oh, so social... socialites, professors, and safecrackers with mafia ties.” — Gordon ([12:15])
• Wild Bill’s bravado:
  “If we’re about to be captured, I’ll shoot you first. After all, I’m your commanding officer.” — recounted by Gordon ([26:34])
• On legacy:
  “The man more responsible than any other for the existence of the Central Intelligence Agency has passed away.” — CIA cable ([41:41])
• David, on modern intelligence:
  “Is it even possible anymore... for a single-minded, really colorful, somewhat deranged person to remake an agency in his image?” ([45:34])

11. Closing Thoughts & Teasers ([48:21]–[49:55])

• McCloskey and Corera wittily muse on living out the “Donovan legacy” at Claridge’s, weaving personal anecdotes with the show's mythos.
• Teasers for upcoming content: special guest to discuss changing nature of espionage (phones, sensors, AI).
• End-of-year reminders and holiday wishes.

Summary:
This episode deftly blends deep historical research, sharp analysis, and personal humor to reconstruct the rise and fall of Wild Bill Donovan and the OSS—the DNA of today’s CIA. The hosts unravel tales equal parts slapstick and gravitas, all while probing the legacy of America’s first “spymaster,” his chaotic organization, and the enduring influence (and cautionary tale) he left on US intelligence culture.

For Listeners New and Old:
A must-listen for fans of history, espionage drama, and those who enjoy their spy lore mixed with a martini—shaken, of course, at Claridge’s.