110. The Man Behind The CIA: Charming Mussolini and Stealing From MI6 (Ep 1)

22 Dec 2025 · 49 min · 16 chapters

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In short

Episode 110 (Ep 1) of The Rest Is Classified is a Christmas special about William “Wild Bill” Donovan, portrayed as the modern founder of the CIA. It traces his rise from a poor first-generation Irish immigrant background in Buffalo (Niagara University, then Columbia Law) and his close early connection to Franklin D. Roosevelt.

Key claims

Donovan’s “tip of the spear” bravery and reckless, theatrical leadership shaped OSS and thus CIA culture; the CIA’s early form was influenced by British intelligence; and US intelligence before the CIA was piecemeal, so Donovan functioned as an unofficial intelligence service for FDR. Notable examples include Donovan’s WWI heroism (Distinguished Service Cross at the Marne; severe leg wound at L’Andre et Saint-Georges) and his pre-WWII access to Mussolini, Franco, and German military maneuvers. The episode highlights a July 1940 MI6 “charm offensive” mission to Britain, using SIS agent William Stevenson (“Intrepid”) to get close to Donovan, and Ian Fleming’s blueprint idea for a centralized US intelligence agency. It ends on Donovan being summoned during the Dec 7, 1941 Pearl Harbor news.

Guests

none mentioned; the episode is hosted by David McCloskey and Gordon Carrera.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Introduction to Major General William Donovan

0:20 to 2:28

Explore the legacy of William Donovan, founder of the OSS.

“Most people are not counter-espionage experts, but that won't stop them getting targeted by cyber criminals seeking to extract their secrets.”

Introduction to Major General William Donovan

2:32 to 3:15

Explore the legacy of William Donovan, founder of the OSS.

“We have come to the end of an unusual experiment.”

The Christmas Spirit and Donovan's Legacy

3:15 to 4:03

Hosts discuss the parallels between Donovan and British intelligence figures.

“And that was Major General William Donovan speaking on September 24th, 1945, at the final gathering, tragic, of personnel of the OSS, the Office of Strategic Services.”

The Eccentricities of Intelligence Leaders

4:03 to 8:00

Delving into the eccentric characters that shaped early intelligence organizations.

“And I think it is a bit of a Christian name.”

Donovan's Background and Education

8:00 to 10:03

A look at Donovan's early life, education, and influential connections.

“which I think is a great way of describing it.”

Marital Life and Military Aspirations

10:03 to 12:39

Discussion of Donovan's marriage and his military ambitions leading up to WWI.

“a first-generation Irish immigrant family, working-class background, so pretty poor, but with a kind of deep commitment to books and learnings.”

The Legend of Wild Bill Donovan

12:39 to 19:03

Exploring the origins of the 'Wild Bill' nickname and Donovan's military exploits.

“So I've gone, for the listeners who really care about this stuff, I've got some entries from Ruth's journal that I'll be reading, her diary, to really kind of bring that to life as Gordon has so callously minimised it.”

Donovan's Post-War Career and Political Struggles

21:14 to 28:00

Follow Wild Bill Donovan's journey from war hero to lawyering and his tumultuous political ambitions.

“Wild Bill Donovan has returned from trench warfare in Europe, I guess to the corporate or sort of business equivalent of trench warfare, which is being a lawyer.”

Donovan's Early Information Gathering

28:00 to 29:52

Learn how Donovan used his reputation to gain access to key figures in Europe during the rise of fascism.

“president will use to understand what's going on in the world, because there just aren't CIA stations around the world.”

The Influence of Frank Knox

29:52 to 31:31

Explore the impact of Frank Knox on Donovan's missions and their shared transatlantic ambitions.

“Because in 1940, Frank Knox sends Donovan to Britain.”
Show all 16 chapters

Britain's Charm Offensive

31:31 to 33:42

Understand how the British leveraged their charm to influence Donovan's perspective on their war efforts.

“Years after Bill Donovan goes over and is brainwashed by the UK establishment, you were funded by Frank Knox money to come over here and be brainwashed by the Washington establishment.”

Donovan's Report and Its Consequences

33:42 to 36:39

Discover how Donovan's assessment affected American support for Britain during WWII.

“And they just, I mean, the access he gets is astonishing because he's still technically a private citizen, even though everyone knows he's the kind of emissary of the US administration.”

Adventures and Misadventures in Europe

36:39 to 40:08

Learn about Donovan's risky travels across Europe and the challenges he faced, including losing crucial intelligence.

“Littman says that Donovan's assessment, quote, almost single-handedly overcame the unmitigated defeatism, which was paralyzing Washington.”

The Blueprint for a Central Intelligence Agency

40:08 to 42:07

Explore how Donovan's interactions with British intelligence shaped the idea of a unified American intelligence agency.

“There's a lot of crazy operations that when you look back, you think it sounds daring, but then you look at it more kind of clear-eyed and you're like, well, a lot of this was disastrous.”

The Role of Donovan in U.S. Intelligence

42:07 to 46:14

Explore the complex role of William Donovan and the evolving landscape of U.S. intelligence during WWII.

“you can imagine how relieved I am after months of battle and jockeying for position in Washington that our man is in a position of such importance to our efforts.”

Pearl Harbor: A Turning Point

46:14 to 47:34

Learn about the significant moment of Pearl Harbor and its impact on Donovan's career.

“1941, when America is attacked by Japan.”
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Transcript

Automatic transcript. May contain errors.

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2:38Gordon:We have come to the end of an unusual experiment. This experiment was to determine whether a group of Americans constituting a cross-section of racial origins, abilities, temperaments, and talents could meet and risk an encounter with the long-established and well-trained army organizations. When I speak of your achievements, that does not mean that we did not make mistakes. We were not afraid to make mistakes because we were not afraid to try things that had not been tried before. You must also have the conviction that this agency in which you played a part was an effective force. Well, welcome to The Rest is Classified.

3:15Gordon:I'm David McCloskey. And I'm Gordon Carrera. And that was Major General William Donovan speaking on September 24th, 1945, at the final gathering, tragic, of personnel of the OSS, the Office of Strategic Services. And Gordon, in this very special and wonderful week of Christmas, we have a special Christmas treat for all of our listeners. we are going to be looking at the life and times of this extraordinary man, William Donovan. I guess we could say this is a pairing with our episode last Christmas on Mansfield Cumming, the founder of British intelligence, because this time we are looking at the man who founded not quite the CIA, but who I think we should probably see as the modern founder of the Central Intelligence Agency.

4:11David:That's right, Bill Donovan. Wild Bill Donovan. Let's give him his full name. And I think it is a bit of a Christian name.

4:18Gordon:His full Christian name.

4:19David:His first Christian, Wild Bill. By the way, for those not watching the video, you didn't get the Christmas memo. I've got my kind of Christmas velvet jacket on. You haven't got a Christmas jumper or anything like that. Maybe we're recording too early for you quite to be in the spirit.

4:34Gordon:Gordon has a smoking jacket on that is not quite in Willy Wonka territory, but close. and while bill donovan territory and i and i am wearing nutcracker socks which you cannot see okay watching on video because they are on my feet but i am very i'm very christmasy from the

4:52David:feet down from the feet down very good say yes well that's right speaking of the feet down last time we did we did mansfield coming um the man who famously would stab himself in his wooden leg with a with a pen knife to see how new recruits would deal with it in mi6 at the start the first of war. This time we're looking at a kind of, yeah, parallel founding figure, this time on the American side. I'm not quite sure he's, I mean, he's wild. I'm not sure he's quite as crazy and as eccentric as the Brits in true American style. He's got his own eccentricities, but he's close, isn't he? He is close.

5:27David:But he's definitely a character, I think. Yeah, I think he's close.

5:30Gordon:What does it say about the intelligence organizations in our two countries, Gordon, that they were both founded by men who were arguably insane. What does that say? What does that tell you? As we'll see, we're just teasing it, but Donovan, I mean, you're right. He doesn't stab himself in the leg while he's conducting interviews. But I mean, as we'll see, I mean, he's pretty bonkers too, right? I mean, he's not a normal. This is not a normal guy. Not a normal guy.

5:56David:No, no. But it's a good question because how far do their kind of cultures, their individual personalities affect the cultures of the organisation. There's a kind of eccentricity to the early MI6. And what Bill Donovan's will see is this kind of larger than life, gung-ho, reckless, I think is one way of putting it, brave, adventuring leader of the early American intelligence community, which I think does play a part, doesn't it, in what CIA becomes and its

6:27Gordon:early culture. I think it is fair to say that even if Donovan does not found or does not lead the CIA in its early years, and the CIA is founded in 1947, Donovan's going to lead the Office of Strategic Services during the Second World War, as we will see. But the CIA is, I think, formed to some extent in the image of the organization that Donovan created and led. And I think there is a kind of, in some parts of the CIA, I guess what you'd call maybe a tip of the spear mentality and wanting to be right where the action is. And frankly, being one of the first organizations that the US government might rely on for covert action or for collecting information in very sort of hostile parts of the globe that is in line very much with the organization that Bill Donovan created and really his personality.

7:21Gordon:I mean, it really is a story that is chock full of insane characters. We're going to focus on Bill Donovan, but he recruits a team of people that is, I would say, less than conventional, Gordon.

7:35David:Glorious amateurs.

7:37Gordon:Glorious amateurs. And I think it was Donovan who believed that the ideal agent, or case officer, rather, was a PhD who could win a bar fight, which is a great description, I think, of what I hope to be someday.

7:53David:Yeah, McGeorge Bundy said, the OSS was a remarkable institution, half cops and robbers and half faculty meeting, which I think is a great way of describing it. Donovan himself is this extraordinary character, certainly larger than life, but it's also a tale, as we'll come to, of institutional warfare, of kind of, you know, backbiting and fighting, but also on the British side, you know, the Brits play a big role in this story. And you've got characters like Ian Fleming, who goes on to write the James Bond novels, as well as the shadowy figures like J. Edgar Hoover and Alan Dulles and others. And we're going to have guns being fired in the White House.

8:29David:So there's plenty of action and intrigue, I think, in the story of Wild Bill Donovan. I mean, he is extraordinary as well, because it's this kind of personal, as we'll see is personal bravery. I mean, you can't imagine, I don't know, current chiefs of CIA or MI6 doing the kinds of things, as we'll see he'll do, where you just pitch up in a war zone or in a frontline operation. It's kind of hard to imagine, isn't it?

8:54Gordon:It is hard to imagine Bill Burns or John Ratcliffe showing up randomly, as we'll see, just kind of appearing in the midst of operations, unannounced. Yes, it is. Hello, I'm here. Yeah, that is hard to imagine. Although, you know what, Gordon, we're getting, I don't know if you're aware of this, we're getting a large new ballroom attached to our White House. And I hear that guns will be allowed. Guns will be allowed. So we might be bringing gunfire in the White House back. It's coming back after all these years. I also think, Gordon, I mean, you're being too modest. Is this the story of the greatest influence operation in the history of British intelligence?

9:33David:Well, those who are cynically minded in Washington might think that this was a case of the Brits playing the Americans and influencing them and trying to get what they want. But I'm not sure it entirely works out the British way. I mean, there is a conspiratorial view that the Brits are always kind of cunningly manipulating the Americans. I think, as we'll see, that's not quite the case, although a little bit of that.

9:54Gordon:But like all good stories, Gordon, this one begins in Buffalo, New York.

9:57David:In Buffalo, New York, New Year's Day, 1883. So his background is interesting, a first-generation Irish immigrant family, working-class background, so pretty poor, but with a kind of deep commitment to books and learnings. I guess what you notice that from the start, he's got this drive, that kind of classic American drive to make something of himself, to improve himself, to kind of go from humble origins to being part of the elite. He's certainly got that hasn't he starts at niagara university and then transfers to columbia more prestigious more of a route into the elite he's smart and athletic quarterback for the varsity football team as well as rowing and cross-country running and then 1905 goes to columbia law school now crucial connection a classmate though not necessarily a close friend is franklin delano Roosevelt, FDR.

10:50David:And I think FDR, it's right, isn't it? FDR is a bit of a higher social status, I think, than Donovan at this time. So I don't think they're kind of quite moving in the same circles. But I think FDR admires Donovan because Donovan is the kind of sports hero of the college. And that lays some interesting roots for an important relationship, which will come later.

11:09Gordon:And I guess after graduating from Columbia Law School, he unsurprisingly goes into legal practice in Buffalo. I have to say that knowing where Wild Bill is going to end up, it is hard to imagine him as a lawyer in Buffalo, which I guess is why he doesn't stay for very long. But he's a good looking guy, isn't he, Gordon? He's good with the ladies, piercing blue eyes, like one of the hosts on this podcast. He dates lots of well-off establishment types. and in 1914 he's going to marry Ruth Rumsel who is an heiress from Buffalo.

11:46David:Yeah and I guess she is from the kind of Protestant elite of the town. He's a kind of working-class Catholic boy. It's fair to say I don't think the marriage is an entirely happy one. He may stray at various points I think as we'll learn but also he just his ambition his driving ambition means he's you just get this feeling he's always going away he's always traveling he's always on the move there's not much of a kind of family life there um very soon actually you know get married in 1914 very soon he's going away because his heroes are men of action you know kind of sportsman military types and he and a group of young men found their own army national guard cavalry unit it's known by them as the businessman's troop uh but others call it the

12:32Gordon:silk stocking boys these are these are these are not very intimidating names i think they should have gone on the name of the unit i'll also say because gordon we know we know from the long history together over the past year on this podcast that you love uh minimizing the personal relations family relations in these kind of shows that you know not this one you get your you get your rocks off kind of editing out the family stuff. So I've gone, for the listeners who really care about this stuff, I've got some entries from Ruth's journal that I'll be reading, her diary, to really kind of bring that to life as Gordon has so callously minimised it.

13:14But yes, go on.

13:17David:And then 1916, his unit is called into federal service for the Mexican border campaign to hunt for Pancho Villa. I mean, well, that's a great fact, isn't it? And he arrives close to you, David, southern border of Texas, 1916. By now he's a major though. And then of course, he gets his chance for action because it's World War I and the US is joining World War I. And this is the kind of making of Donovan and of the legend. He is part of the 69th Fighting Irish Regiment of New York.

13:46Gordon:Better name. That's better than the silk stocking boys.

13:49David:Yeah. Which becomes part of the 165th Infantry and the 42nd Rainbow Division formed from National Guard units. The division's chief of staff was Douglas MacArthur, later an important general. They're going to end up rivals, first of many rivalries. Now, this is where the legend of Wild Bill comes from. One theory says the nickname Wild Bill came from his ferociousness on the football field at Columbia. But according to Douglas Waller, who's author of by far the best book on Donovan called Wild Bill Donovan, the spymaster who created the OSS, it came from pushing his men and himself so he's training his men so he runs them in full packs on a three-mile obstacle course over walls under barbed wire through icy streams up and down the hills the men are collapsing they're gasping for air and he says what's what the hell is the matter with you guys and he's 35 years old and he's been carrying the same load as all these younger men and he says i haven't lost my breath and a trooper in the back whom donovan couldn't see shouted but hell we're not as wild as you are bill i mean that's how to get a nickname and and supposedly he kind of goes oh i hate this nickname it's so awful you know i'm but actually uh ruth his wife says deep down he loves it i mean who wouldn't love a nickname like being wild bill oh it's a great

Read the full transcript

15:10Gordon:nickname but wasn't there a rumor that he was it was named wild bill after a new york yankees pitcher who maybe actually was the manager was the manager during the first world war who was very he threw the ball very fast, but he didn't throw it very accurately. So there's all kinds of, I like the war story better though. That's better than just being named after a random pitcher.

15:31David:Yeah. And the thing is, he does live up to the name in war because he's a really demanding leader, but he leads by example and from the front. And this is the kind of one of the facets of his character. He's totally fearless. I mean, some people think he really actually enjoys combat. so July 1918 he gets awarded the Distinguished Service Cross for Valour during the Marne campaign and according to the citation he leads his battalion in advance of the division for four days all the while under shell and machine gun fire the enemy are on three sides of him he's repeatedly and persistently counter-attacked and is wounded twice and the Irish regiment loses nearly half his men.

16:11David:A few months later, his reputation for near-suicidal bravery is cemented at L 'Andre et Saint-Georges, which is a big battle, which is actually something of a military defeat, which is interesting.

16:26Gordon:Your French has gotten a lot better on the podcast, Gordon. I've been practicing. I don't want to be humiliated by you. I was going to say, your French has gotten...

16:33David:After our early Rainbow Warrior episodes. But anyway, here at this battle of L 'Andre at Saint-Georges. Donovan personally leads an assaulting wave against a heavily fortified German position. And his unit is full of nervous new recruits. And then in this act, which is very him, of theatrical leadership, he ignores the custom of covering or stripping off his own insignia or rank in case he's targeted by enemy snipers. And he goes forward wearing his medals, wearing his rank, making himself a target to inspire his men. And he's reportedly heard shouting, they can't hit me and they won't hit you.

17:11David:And during this battle, he gets shot into his leg, refuses to be evacuated, continues with his unit, reorganizing positions, leading them for five hours. By the end, he's groggy and barely conscious, but he survives.

17:27Gordon:Well, yet another overlap with Mansfield coming is serious leg problems. Mansfield coming in that car wreck had apparently, well, according to the legend, cut off his own leg to extract himself

17:41David:from the car wreck.

17:43Gordon:And now here we have Wild Bill being machine gunned in a leg during the First World War. So yet another spooky overlap between our transatlantic spymaster founders.

17:54David:And what's interesting, he's a bit of a rule breaker. And Douglas MacArthur, who's in command there, thinks Donovan pushes his units too far forward and is, quote, running wild. But he finishes the war as one of the most highly decorated soldiers in World War and possibly the most highly decorated American in World War I. This is kind of serious bravery. He's got multiple medals, multiple citations. And so this legend is born of a daring, kind of brilliant, theatrical, rule-breaking, reckless leader and soldier who doesn't shy from the fight and wants to be where the action is, which I guess is the model which is going to be created for OSS.

18:39Gordon:I guess another theme emerging here in his struggles against MacArthur is going to be, and maybe it's just another feature of him relishing conflict, because Wild Bill seems to get along with nobody else inside the DC establishment and inside the Pentagon. But maybe there, Gordon, with Wild Bill emerging from the trenches of World War I hero. Let's take a break and when we come back, we will see how he begins to found the modern OSS.

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21:13Gordon:Well, welcome back. Wild Bill Donovan has returned from trench warfare in Europe, I guess to the corporate or sort of business equivalent of trench warfare, which is being a lawyer. And he is now lawyering, but starting, I guess, Gordon, to do some work on the side for his old Columbia Law School pal, FDR.

21:37David:Yeah, it's very interesting because he starts a kind of double life because he's obviously got this great reputation, hasn't he, as a war hero. And straight away, 1919, he goes on a combined vacation and business trip to Japan, China, and Korea with his wife, with Ruth. But then almost immediately he gets asked by, I think, an American ambassador, would you mind going to Siberia for a little bit of extra work? And he ditches Ruth straight away. I mean, he's only just finished the war and he's - He's back at it. Yeah, he's back into action. And so he's asked to go on a mission to evaluate the state of forces in the Russian civil war and also what Japan is up to in what's now the Soviet Union.

22:21David:So poor old Ruth, she heads back to the US alone and I guess a little bit bitter.

22:27Gordon:I promised listeners that there would be entries from Ruth Donovan's diary. And here's one from this era, and it actually appears several times. Bill out, bed early. This was a very common entry in Ruth's diary in this time period after the war. So he's just gone constantly and she goes to bed early.

22:51David:So he's doing his lawyering, but then he gets appointed to some interesting positions. From 1922 to 1924, he serves as the US attorney for the Western District of New York, and he becomes a big crime buster, going after gangs, making lots of enemies. But of course, this is also that bizarre period of American life called Prohibition, David, which seems impossible to understand for any foreigner when alcohol was banned. Well, it's a drug, Gordon. It's a drug. It's not good for you. Yeah, that's why it never passes your lips. So Donovan is here kind of enforcing that. Amongst other things, he does a big raid on something called the Saturn Club in Buffalo, which is where the city elite drinks.

23:38David:But unfortunately, he is also a member of the Saturn Club and his wife's family are very influential in the Saturn Club. I mean, I guess he's putting his duties first, but I don't think they entirely ever forgive him for raiding their speakeasy club.

23:54Gordon:See, this makes the behavior on the battlefield, I think, make even more sense because he actually just loves fighting. But I guess then after his stint as the U.S. attorney for the Western District of New York, he is brought back to Washington.

24:10David:Yeah, President Calvin Coolidge, who's a Republican, appoints him Assistant Attorney General. First, the Criminal Division, later Antitrust Division. Now here, the kind of bureaucratic warfare really begins because he's going to meet the man who will become his nemesis, his arch rival. None other than J. Edgar Hoover. Hoover, of course, is made first Director of the Bureau of Investigation in 1924, which then gets renamed the FBI in 1935. This is the origin of the Thebes, isn't it, David? Well, they're not quite your nemesis, but your rivals, I guess.

24:46Gordon:We've established in recent episodes, perhaps, that my nemesis is the Defense Intelligence Agency. But on any given day, my bureaucratic bugaboos could be shifting to all manner of other institutions that are not the central intelligence agency. But yes, go on.

25:03David:And Donovan is actually Hoover's boss in Washington at first. And of course, he starts intervening and then he starts clashing with Hoover. And then I love the fact they both basically start keeping dirt on each other. It's like, welcome to Washington. They're basically going to start files on each other and kind of maneuvering against each other. It's the start of a pretty bitter feud right from, you know, kind of the mid-20s onwards for a good 20 years, if not 30 years, I guess.

25:28Gordon:Well, and I guess Donovan is sort of dabbling in politics at this time, right? I mean, he runs unsuccessfully to be the lieutenant governor of New York. Later, he's a Republican candidate to succeed FDR as governor in 1932. But I guess this will also be a theme of Bill Donovan is that he's not a great campaigner. I would say he's actually terrible at politics, as we'll see from the number of conflicts that he has with everybody that he interacts with in Washington. He's also poorly organized, I would say. So he's not maybe your ideal politician. He's not the front guy.

26:08David:Yeah, it's interesting, isn't it? Because I think he thought, and a lot of people around him thought, he would end up president. He's working up the Republican Party, but he never quite makes it as an elected politician. So in parallel, he's going to found a big Wall Street law firm, particularly because he hoped to be made attorney general in 1929. He doesn't get the nod. But then it's interesting because he's a Republican. FDR is now president. Donovan is quite critical, I think, of FDR and the New Deal and does interviews, having a go at it. And yet there's a kind of back-channel friendship relationship between those two men, which I think is really interesting.

26:45David:because FDR has always admired Donovan because of his sportsmanship back when they were university students. And also, I think that kind of, you get the feeling they're both internationalists, and that's going to play a big role in the coming year, as Donovan takes on this interesting role because he's going to travel the world as a lawyer, but also kind of keep in contact with people in Washington, including FDR, about what he's seeing. And this is partly, I guess, a result, David, which seems strange that the US didn't have an intelligence service collecting foreign intelligence at that time, did it?

27:21Gordon:No. And I mean, there's a great line in Tim Weiner's book on the CIA, which is called Legacy of Ashes. And in this kind of early period, before you actually have a central intelligence agency, Tim Weiner says that most of what the US government knew about the world could fit into a couple filing cabinets inside the Department of State, right? So there wasn't an official intelligence presence abroad. And as a result, I guess, guys like Bill Donovan, who are traveling extensively and have a deep kind of bench of international contacts, end up becoming kind of the unofficial intelligence service that FDR, that the American president will use to understand what's going on in the world, because there just aren't CIA stations around the world.

28:09Gordon:And frankly, there's a lot of capitals where the US doesn't even have an embassy or an ambassador. So our ability to just collect information was so limited, which is almost impossible to imagine today.

28:18David:Yeah. And so it's interesting because Donovan goes primarily as a lawyer and as a businessman on all these trips representing clients. But for instance, he goes to Rome and Mussolini has just taken power, the kind of fascist leader in Rome. And because Donovan is this war hero and this kind of famous guy, doors are open for him. Mussolini meets him and as a result Donovan is able to say I'd quite like to visit you know Ethiopia which Italy has just invaded and Mussolini kind of goes yeah sure because it's Donovan and so he gets this kind of access to people because of his reputation which is really interesting and gets to go to places and go to countries which other people can't and then report back and he also goes he goes to Spain study the Spanish Civil War and he meets Franco there leader of the nationalist side.

29:07David:And he goes to Germany, goes to Berlin to observe German military manoeuvres and exercises, technically there to do work for clients. But it means he's got this feel for what's happening in Europe, which I think very few other people would have had at the time. And he's able to then report back to people in Washington. And that's going to reach his friend FDR as well, who are going to be interested in what's his view of what's happening on the ground.

29:34Gordon:And I guess just as the Second World War is breaking out, this is when Donovan begins traveling and actually gets sent to Britain at the behest of the Secretary of the Navy, a guy named Frank Knox. And Gordon, you're in debt to Frank Knox. Is that right?

29:52David:I am. So this is very interesting. So 1940s, he's been doing these missions, but this is his first informal but most significant mission donovan actually hoped at the 1940 to be made secretary of war but he doesn't get it and but frank knox who is a republican another republican sends donovan on a mission to britain now this is where there are many close parallels between me and wild bill donovan reckless bravery brilliant sportsmanship but we've both both me and wild Bill, being sent on transatlantic missions supported by Frank Knox. Because in 1940, Frank Knox sends Donovan to Britain. But after his death, Frank Knox's family bequeathed a load of money to set up something called the Frank Knox Fellowship to improve transatlantic relations.

30:42David:And I was a Frank Knox Fellow. So I was supported by the Frank Knox Fellowship to go to the United States. So a kind of parallel mission to build relationships between the two countries, which I like to think was, as we'll see, of equal importance to Frank Knox's July 1940 mission to Britain. But we both owe a debt to Frank Knox in that sense.

31:04Gordon:I'm glad to see that there continues to be a pot of money used to enable British influence operations against the United States of America, which I did not know until this podcast.

31:15David:This is an American influence operation. There's money left by an American to send poor impressionable Brits like me over to the US. And I have to say, it was quite generous because I'd been an undergraduate living on baked beans. And then I was suddenly like a graduate student living on this Frank Knox fellowship. And it felt pretty good. Oh, true. It's actually the reverse.

31:34Gordon:We're enabling the reverse. It's the reverse. Yeah. Years after Bill Donovan goes over and is brainwashed by the UK establishment, you were funded by Frank Knox money to come over here and be brainwashed by the Washington establishment.

31:49David:Exactly. Another bizarre parallel between me and Bill Donovan. But Frank Knox is going to send Donovan on this mission, back to him, July 1940. And this is absolutely crucial, this mission, because July 1940, France has fallen, the low countries have fallen to the Nazis as the kind of German war machine has crushed most of Western Europe. And Britain is standing alone, famously. And the big question people are asking in Washington is, can Britain survive or is it too going to fall? And interestingly enough, the US ambassador in London is sceptical. He's quite a defeatist, arguably a bit of an appeaser.

32:31David:And who is that? None other than Joseph Kennedy, father of JFK. So Joe Kennedy is there in London as ambassador to the court of St. James, as the American ambassador is called. And it's kind of like a negative influence when it comes to British-American relationships. And that's why Donovan's mission, I think, is so important.

32:52Gordon:And this is where the influence operation comes in, right, Gordon? Because you haven't had any luck influencing the actual ambassador, Joseph B. Kennedy. And now you've got this emissary who's sent over to, I guess, put together kind of a perspective on whether Britain is going to be able to hold out. And it's very important that Bill Donovan return to Washington with an affirmative, but also reporting back, I guess, on the need for American assistance to stand up, for the UK to stand up to Germany, right? So there's a very clear message that the Brits need to deliver to Bill Donovan during his mission.

33:39David:And boy, do they turn on the charm. I mean, this is something which I find really interesting because they know how important Donovan's visit is in July 1940. And they just, I mean, the access he gets is astonishing because he's still technically a private citizen, even though everyone knows he's the kind of emissary of the US administration. So seven people are assigned to answer his questions because he's briefed on the industry, the economies taken to military facilities. He is going to meet the MI5 officers. He's going to meet the new head of MI6. He's going to meet the king and queen. Now, this again is making modern parallels.

34:20David:Occasionally, as we saw recently with your current president, the royal family is deployed to turn on the charm for visiting Americans. You know, it's a very deliberate act. Let's bring the royals out and have them meet the American visitor to kind of turn on the full kind of British thing. And they do that. And he's going to meet like kind of London socialites. I'm sure he enjoys meeting the women folk and I think they enjoy meeting him and he's quite famous for that. So it's a kind of full court press by the Brits to basically give him absolutely all the access he could possibly want.

34:56Gordon:Is it going too far, Gordon, to say that SIS, MI6, they actually had an agent that they used to get close to Bill Donovan? There was a Canadian businessman named William Stevenson, codename Intrepid. So he actually had a codename who was a self-made millionaire, former lightweight boxing champion. So you can see how Donovan would get along well with him because they both love fighting. Stevenson had been a very decorated World War I hero, and they get very close to each other, become great friends. And this guy is on the SIS sort of payroll. So I mean, there's a straight line from the creation of the CIA straight back to all of this sort of British shenanigans, Gordon.

35:43Gordon:What say you?

35:44David:Yeah, national survival. I think that is exactly what they're doing. They recognise Bill Donovan is a man to impress, and they know how to impress him. They do it. They feed him talking points. They feed him talking points. They feed him talking points. I mean, look, this is wartime survival. This is what you do. Dare I say, I think this still occasionally happens with visiting Americans. As I said, with presidents, but also with CIA directors and everyone else. You know, the Brits turn on the charm for them. They do their best. They know they've got to win them over. You're not trying to recruit them as an agent.

36:18David:You're trying to win them over to your side. And it works, we should say. And it works. It works.

36:23Gordon:It works big time because Walter Lippman, who's probably one of the most prominent American political columnists of the day, says that Donovan, who returns from his sort of glamorous trip to the UK, now fully on board, I think, with the war mission. Littman says that Donovan's assessment, quote, almost single-handedly overcame the unmitigated defeatism, which was paralyzing Washington. That report, Gordon, ended up being a crucial factor in securing US aid and the Lend-Lease program that would save your fair isles from the Nazi war machine.

37:01David:Yeah. Donovan's going to brief his old friend Roosevelt personally on a train ride and say that they can win if we support them. That's the message. And then he comes back for another visit, December 1940. Interestingly enough, this visit is paid for by the Brits, I was reading, which seems amazing. He spends some time with Churchill. They get on well because obviously two men who like the military. Although I think I read somewhere that Donovan finds when Churchill goes off on one of his monologues, kind of gets a little bit tired of it. And obviously it doesn't show that. But here's what's really interesting.

37:32David:MI6 then offered to take Donovan on a tour of the kind of hot spots of the conflict. so they're like do you want to go out there into the field and of course this is Donovan so he's like sure and so New Year's Day Donovan which is also of course his birthday Donovan is aboard an RAF plane skirting German fighters over France en route to Gibraltar and dining I love this detail on a picnic provided by Lord Mountbatten which is three bottles of Moselle a flask of hot turtle soup, fresh lobster, cold pheasant, and Stilton cheese served by an orderly in a white jacket and white gloves. That is how the Brits turn on the charm for their visiting Americans.

38:16David:That's how you do it, David. Whenever you come over, that's what I offer you, isn't it? That's right.

38:20Gordon:Whenever I come over, Gordon always is waiting with a flask of turtle soup at Heathrow for my arrival. And he's wearing his sort of velvet smoking jacket that he has on right now. I've always, I have been confused. I'll admit, I probably answered this question just by Googling it, but I'm going to ask you, Gordon, because you're a sophisticated Brit who knows the answer. What parts of the turtle are in the turtle soup?

38:47David:I don't know. I'm going to confess. This is going to show my limited social status. I'm more of a kind of, you know, wild Bill Aravest rather than a proper posh bloke because I've never had turtle soup. You've never had turtle soup. I just think you boil the turtle. I don't know. And then.

39:03Gordon:okay look look becky becky our intrepid producer uh becky has said it's meat from the legs neck tail and belly often with the bones for stock so there you go okay that i guess that makes sense

39:16David:always making that yeah um so here let's go back to donovan and he's so this trip around europe is is crazy because at the same time he's going around the whole of the mediterranean and north Africa, the German ad there are also tracking him across Europe because they know he's influential in trouble. And at one point he's in a nightclub in Bulgaria with a British spy and the Germans break into his room and steal his bag, which has a list of his kind of intelligence questions, his intelligence requirements, which he wants answered, which is actually quite, you know, it's quite bad to lose that to the Germans.

39:52David:They also put out the story of he was drunk in the club.

39:54Gordon:The worst possible thing you could do is you lose all of your intelligence questions to the Germans.

39:59David:Go to a nightclub with a British spy, get drunk, and have your stuff stolen by the advert. I mean, but this is a kind of crazy bit of Donovan, isn't it? He kind of just gets away with it. That's what he is.

40:10Gordon:There is going to be a theme here, and it sort of breaks my heart to say this, which is that, as we'll see when we get kind of into the creation of the OSS and the things the OSS gets up to, a lot of this stuff doesn't go very well. Let's just put it that way. There's a lot of crazy operations that when you look back, you think it sounds daring, but then you look at it more kind of clear-eyed and you're like, well, a lot of this was disastrous. A lot of this did not go very well. Getting drunk and having your documents stolen will just be one story among many.

40:40David:But the Brits are also going to do more than just influence him to be supportive. They're also going to give him an idea. And this is the idea of having a single or centralized intelligence agency. and they are kind of feeding him this pan. Now, interestingly enough, Donovan is introduced to Admiral John Godfrey, who is the Royal Navy's Director of Intelligence, and Godfrey is accompanied by his aide, Commander Ian Fleming, the future creator of James Bond. And Fleming and Donovan, again, maybe unsurprisingly, get on. And Fleming is going to plant the idea in Donovan's head about the need for a kind of single integrated intelligence service.

41:23David:And the two men are going to travel. Fleming takes Donovan around Gibraltar during this kind of famous tour. And eventually, Ian Fleming is going to draft a memorandum to Donovan, which lays out the structure for an American intelligence agency. And as a token of his appreciation, Donovan gives Fleming a Colt 38 revolver, symbolically inscribed for special services. I love that. And Fleming would boast that this gun was his reward for writing the blueprint of the CIA.

41:56Gordon:See, British hands all over this. I mean, here's another one from Bill Stevenson, codenamed Intrepid, MI6 agent, who had been tasked with getting close to Donovan. He actually cables C back at head office at London and writes, quote, Donovan accuses me of having intrigued and driven him into the appointment. you can imagine how relieved I am after months of battle and jockeying for position in Washington that our man is in a position of such importance to our efforts. Of course, writing after Donovan will take over OSS. But I guess the point here with all of this talk of what would the blueprint be, what would a central intelligence agency or even just a kind of more formalized U.S.

42:37Gordon:intelligence agency even look like, is that when Donovan returns to DC in March, it's just a bureaucratic mess, isn't it? Because there's a bunch of different intelligence services tucked into pockets of different federal agencies around Washington. And it's not at all clear, from the American perspective, what that blueprint would be.

42:58David:I mean, it's crazy, isn't it? You've got army intelligence, you've got an office of naval intelligence you've got hoover at the fbi you know fdr is clearly a bit frustrated by this piecemeal and stovepiped intelligence system he's got so he's going to take up this idea and initially create uh something called the office of the coordinator of information which is going to be created in july 1941 and he's going to put donovan in charge of it so that is that is donovan's first job. It's not quite the OSS because technically this is just a kind of person whose job it is to be a presidential advisor, I guess, and corral the information from different places.

43:38David:And, you know, Roosevelt says publicly this office won't supersede or duplicate other departments, which is, I think, clearly a bit of a fiction because it is clearly the genesis of a new thing. It's like the proto-DNI, isn't it?

43:53Gordon:Yeah. Yeah.

43:53David:Director of National Intelligence. Exactly. But of course, you know, immediately, who's back is that going to put up? It's Hoover and the FBI, because Hoover is such a kind of wily operator, isn't he? And he really did think that the FBI had the potential to be not just a domestic investigative service, but actually the worldwide intelligence gathering service, you know, to be much broader than we think of it.

44:19Gordon:That was his vision and what he was trying to achieve. Well, I guess Hoover, I mean, he's got a massive counter espionage service within the FBI that's got millions of records and files. Of course, he doesn't want to give that up. I mean, he's even got, which I guess is not really surprising given what we know about J. Edgar Hoover, but he's got a dossier on Donovan himself, right? He's looking at Donovan's extramarital affairs. So Hoover's tracking all of this as dirt, kind of hold it as potential dirt on Donovan.

44:48David:I mean, Hoover is even tracking the kind of travels of Donovan around Europe, because he's kind of going, who's out there? What's he up to? He's kind of trying to understand who's influencing him. He's building that kind of dossier on Donovan. And also, you've got the military who are not very happy with Donovan suddenly appearing on the scene and giving up their intelligence outfit. But I guess FDR, the way he managed intelligence, and what managed all this kind of, the whole way he ran his government was he liked to kind of have different power centres, play people off, not have it very structured.

45:19David:And I think you can see that he kind of views Donovan as very useful in this role. Initially, it's more like a personal emissary. as a kind of an intelligence advisor.

45:29Gordon:And maybe it also helps that Donovan is so bad at the politics. He's just kind of a guy that Roosevelt can use to collect interesting information and who Donovan himself is not going to be capable of creating, knitting together all of these different agencies into one, and which potentially, I guess, could be threatening to Roosevelt himself, right? So Donovan is kind of, he's useful also because his source of legitimacy and power Donovan's is his relationship to FDR. And there's really nothing else in the system that allows Donovan to carry weight.

46:05David:Yeah. And so initially, it's just this one office. And I guess the pivotal moment, which will shift things again, will be Pearl Harbor in December 1941, when America is attacked by Japan.

46:18Gordon:Gordon, I did not know this. Donovan's at a football game that day. He's at the Polo Grounds in New York on Sunday, December 7th, 1941. 55 ,000 fans there are watching the New York Giants play the Brooklyn Dodgers. And I have to admit, Gordon, when I read this in your outline, I thought that you had mistaken the Dodgers, which are, of course, a very legendary baseball franchise, with a football team. And upon my further researches, and I hope to entrap you with baseball trivia, I discovered that, no, in fact, the Brooklyn Dodgers were a football team between the early 30s and 1943. So there we go.

46:54Gordon:And Donovan is summoned over the loudspeaker at this game.

46:58David:But during the games, and it's big games going on, 55 ,000 people, a voice comes on the loudspeaker and it goes, attention, please. Here's an urgent message. Will Colonel William J. Donovan call operator 19 in Washington immediately? You know, dramatic message. And it sends him to a phone booth under the bleachers to actually make the call. And then he hears that Japan's hit Pearl Harbor, and that means he's needed in Washington.

47:27Gordon:Oh, Gordon, that's a good cliffhanger. So maybe there with William Donovan making the phone call of his life. Let's end the episode when we come back next time on Christmas Eve, no less. We will see how William Donovan creates the Office of Strategic Services, America's first intelligence agency.

47:48David:But if you can't wait, if you can't wait till Christmas Eve, if your Christmas Eve is busy with wrapping presents and you want to listen now, you can. Put on your smoking jacket, join the Declassified Club at therestisclassified.com and you can get early access. And of course, you can get access to tickets for our live show. Don't forget that, 31st of January at the South

48:09Gordon:Bank here in London. That's right. Oh, and also, maybe follow us on Instagram, Gordon, as a little holiday treat for yourself. You can follow us at the handle at rest is classified. But happy holidays. And we'll see you on Christmas Eve. See you then.

48:35Gordon:In intelligence, information is only as reliable as the source behind it. It can sound convincing, but the real test is whether it holds up under scrutiny.

48:43David:And for brands, the same principle holds. It may not be called tradecraft in a media plan, but a message is only as credible as the channel it moves through.

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From the publisher

“Wild” Bill Donovan laid the template for the formation of the modern CIA, but this wasn’t the way his life was supposed to turn out. A working class boy from Buffalo, Bill dreamt of something better for himself. These dreams took him to the trenches of Belgium and the beaches of Normandy, then to the halls of power themselves. 

This is the story of the man behind the CIA. From decorated war hero to an eccentric establishment figure, listen as David and Gordon tell the story of Wild Bill Donovan.

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