The Rest Is Classified – Episode 110

"The Man Behind The CIA: Charming Mussolini and Stealing From MI6 (Ep 1)"
Hosts: David McCloskey (Former CIA analyst & spy novelist) and Gordon Corera (Veteran security correspondent)
Date: December 22, 2025

Overview

In this episode, David McCloskey and Gordon Corera kick off a two-part holiday special by delving deep into the life and legend of Major General William “Wild Bill” Donovan—the founder of the Office of Strategic Services (OSS) and the spiritual father of the CIA. The hosts draw lively comparisons between American and British intelligence origins and personalities, focusing on Donovan’s larger-than-life legacy, the wildness and eccentricity that shaped the American spook tradition, and the tangled Anglo-American intelligence relationship, where MI6's influence played a crucial role. Memorable moments, personal anecdotes, and behind-the-scenes power plays abound in this episode, setting the stage for the birth of modern American intelligence.

Key Discussion Points and Insights

1. Origins of Intelligence Agencies – American & British Parallels

• Donovan vs. Cumming:
  The episode opens with comparisons between the American Donovan and British Mansfield Cumming (“C”), the MI6 founder. Both men are depicted as eccentric pioneers whose personalities shaped their institutions.
  • "What does it say about the intelligence organizations in our two countries, Gordon, that they were both founded by men who were arguably insane?" – David [05:51]
• Culture Influenced by Founders:
  Donovan’s “gung ho, reckless” style becomes cultural DNA for the OSS and later the CIA.
  • "Wild Bill Donovan’s... larger than life gung-ho, reckless, I think is one way of putting it—brave, adventuring leader of the early American intelligence community..." – Gordon [06:18]

2. Donovan’s Early Life – Buffalo to the Battlefield

• American Dream Roots:
  Born in 1883 to poor Irish immigrants in Buffalo, New York, Donovan embodies the self-made man—athlete, Columbia Law classmate of FDR, and driven “from humble origins to being part of the elite.”
  • "He’s smart and athletic. Quarterback for the varsity football team as well as rowing and cross country running." – Gordon [11:06]
• Personal Life:
  Donovan marries into the Protestant elite, but his marriage is tumultuous due to constant absences and his restless ambition.
  • Ruth Donovan diary entry: "Bill out bed early." – David [24:13], quoting Ruth

3. WWI Heroics—Where “Wild Bill” is Born

• Legend Begins:
  Donovan leads the “69th Fighting Irish” and earns his nickname through grueling training and battlefield bravery.
  • "What the hell's the matter with you guys? ...I haven't lost my breath." – Story of Donovan's leadership, Gordon [14:07]
  • Earns the Distinguished Service Cross and other honors for acts of reckless valor, e.g., leading charges while wounded and refusing to remove his insignia under German fire.
  • "They can’t hit me and they won’t hit you." – Gordon [16:55] (Donovan allegedly shouting to men under fire)
• Parallel with British Spy Legends:
  Both Donovan and Cumming suffer severe leg injuries—an ironic link in transatlantic espionage folklore.
  • "Yet another overlap with Mansfield Cumming... Spooky overlap between our... spymaster founders." – David [17:49]

4. Interwar Adventures: Law, Politics, and Proxy Espionage

• Return as a Lawyer and ‘Crimebuster’:
  As US Attorney in Prohibition-era Buffalo, Donovan raids elite speakeasies he himself frequents, establishing a penchant for conflict with allies and rivals alike.
  • "He does a big raid on something called the Saturn Club in Buffalo, which is where the city elite drinks. But unfortunately, he… is also a member of the Saturn Club." – Gordon [25:05]
• Washington Bureaucratic Wars:
  Donovan’s rivalry with J. Edgar Hoover (FBI) begins in the 1920s as both men keep dirt files on one another.
  • "They both basically start keeping dirt on each other. Welcome to Washington." – Gordon [26:48]
• Political Failure:
  Despite sky-high ambitions, Donovan fails as an electoral politician but becomes a Wall Street legal powerhouse and international traveler.

5. The Unofficial Spy: Missions Abroad and Early British Influence

• Donovan as Unofficial Intelligence Resource:
  In an era before the CIA, he becomes FDR’s roving eyes and ears overseas thanks to wide-ranging travels for legal work, gaining extraordinary access to world leaders (Mussolini, Franco, etc.)
• UK Mission—Pivot in US-UK Intelligence Collaboration:
  In 1940, as Britain stands alone against Hitler, Donovan (sent by Navy Sec. Frank Knox) is targeted by a full-court MI6/British government charm offensive.
  • "The Brits turn on the charm… he is going to meet MI5 officers, the head of MI6, the King and Queen… full court press." – Gordon [35:23]
  • Canadian MI6 agent William “Intrepid” Stevenson becomes Donovan’s handler (“agent”), feeding him talking points to influence US policy.
  • "SIS, MI6… actually had an agent that they used to get close to Bill Donovan… There’s a straight line from the creation of the CIA straight back to all of this British shenanigans." – David [36:41]
• Direct Impact:
  Walter Lippman: Donovan’s assessment “almost single-handedly overcame the unmitigated defeatism which was paralyzing Washington,” helping to unlock American support and Lend-Lease for the UK.
  • "Donovan's assessment… was a crucial factor in securing US aid..." – David [38:07]

6. Espionage Mishaps and Colorful Episodes

• Clandestine Risks:
  Donovan’s tours of wartime Europe are tracked by German intelligence; he loses a bag of intelligence questions to the Abwehr in Bulgaria after nightclub carousing.
  • "Go to a nightclub with a British spy, get drunk and have your stuff stolen by the Abwehr." – Gordon [41:44]
• Influence and Ideas:
  Key Brit contacts (notably Ian Fleming, future James Bond creator) explicitly propose the unified intelligence agency model to Donovan:
  • "Fleming would boast that this gun was his reward for writing the blueprint of the CIA." – Gordon [43:41]

7. American Intelligence Pre-History: The Birth of Coordination

• Chaos in Intelligence Structure:
  1941: FDR creates the “Coordinator of Information” role for Donovan, precursor to OSS, modeled on British advice and meant to untangle stovepiped military/agency intelligence.
  • "It’s just a bureaucratic mess, isn’t it? …not at all clear from the American perspective…" – David [44:42]

8. Rivalry and Resistance—Bureaucratic Battleground

• J. Edgar Hoover’s Sabotage:
  Hoover resists creation of new agencies, amassing dirt and surveilling Donovan—hopeful the FBI will reign supreme.
  • "He’s looking at Donovan’s extramarital affairs. Hoover’s tracking all of this as dirt…" – David [46:06]
• Roosevelt’s Motives:
  FDR leverages Donovan’s personal loyalty and lack of political skill to manage him as a useful but nonthreatening operator.

9. Pearl Harbor Cliffhanger—A Nation at War

• Dramatic Wartime Mobilization:
  December 7, 1941: Donovan is at a Giants-Dodgers football game when summoned over the loudspeaker to take a critical call. He learns of Pearl Harbor and heads to Washington, foreshadowing the official birth of American intelligence.
  • "A voice comes on the loudspeaker, and it goes, 'Attention, please… Will Colonel William J. Donovan call operator 19 in Washington immediately.'" – Gordon [48:42]
  • "It sends him to a phone booth under the bleachers to actually make the call." – David [49:01]

Notable Quotes & Memorable Moments

• Donovan’s Leadership Style:
  "Glorious amateurs! …the ideal agent… a PhD who could win a bar fight." – David [07:59]
• On OSS Culture:
  "Half cops and robbers and half faculty meeting." – McGeorge Bundy, quoted by Gordon [08:15]
• British "Charm Offensive":
  "The Brits turn on the charm… King and Queen… full court press…" – Gordon [35:23]
• Espionage Fiasco:
  "Go to a nightclub with a British spy, get drunk and have your stuff stolen by the Abwehr." – Gordon [41:44]
• Ian Fleming’s Influence:
  "Fleming would boast that this gun was his reward for writing the blueprint of the CIA." – Gordon [43:41]
• On Bureaucratic Resistance:
  "Donovan is… not great at politics; he’s actually terrible at politics as we’ll see… He’s not the front guy." – David [27:13]
• Washington Espionage Drama:
  "They both basically start keeping dirt on each other. Welcome to Washington." – Gordon [26:48]

Timestamps for Key Segments

• 03:01 — Donovan’s 1945 OSS farewell speech; episode intro
• 05:51 — Parallels between Donovan and British intelligence founder Mansfield Cumming
• 10:19 — Donovan’s early life and Columbia Law; FDR connection
• 14:07 — WWI heroics; origin of the “Wild Bill” nickname
• 24:13 — Ruth Donovan’s diary; personal sacrifices
• 25:05 — Prohibition-era exploits as U.S. Attorney
• 26:48 — Start of rivalry with J. Edgar Hoover
• 29:06 — Absence of US foreign intelligence prior to WWII
• 31:18 — Pre-WWII travel missions; access to Mussolini, Franco, etc.
• 35:23 — British charm offensive in 1940; Joseph Kennedy's defeatism
• 36:41 — MI6/William Stevenson as Donovan’s handler; direct influence
• 38:07 — Impact of Donovan’s reporting on Lend-Lease/American support
• 41:44 — Clandestine mishaps: Donovan’s bag stolen by the Abwehr
• 43:41 — Ian Fleming writes blueprint for CIA; gifted revolver
• 44:42 — Early haphazard U.S. intelligence structure
• 46:06 — Hoover’s opposition and compiling dirt on Donovan
• 48:42 — Donovan summoned from football game at Pearl Harbor
• 49:11 — Episode cliffhanger: birth of OSS coming next

Tone & Personality

The episode is lively, witty, and full of personality, with hosts ribbing each other, weaving personal anecdotes (e.g., Gordon’s Frank Knox fellowship, Christmas outfits), and playfully jabbing at Anglo-American stereotypes of spies and bureaucrats. Crucially, both hosts approach the history with a critical but affectionate tone, skeptical of American and British myths yet clearly enjoying spy lore.

Next Episode Tease

The story will continue with the birth of the OSS and the wild episodes that mark America’s entry into the shadow world of organized intelligence.

For listeners new to the world of intelligence history, this episode offers a captivating, detailed, and highly entertaining deep dive into the quirks, rivalries, and historic turning points that led to the creation of the CIA.