The Rest Is Classified - 111. The Man Behind The CIA: Shooting In The White House (Ep 2)

Episode Date: December 24, 2025

Bill Donovan has set himself up across an entire floor of the swanky London hotel, Claridge’s. From here he is now running international intelligence operations and laying plans for the future of espionage in the United States. But, his arch nemesis, J. Edgar Hoover has an alternative vision for how these lofty ideas should play out. Listen as David and Gordon continue their tale of Wild Bill Donovan: the man who laid the foundations for the modern CIA.  ------------------- Make someone a Declassified Club Member this Christmas – go deeper into the world of espionage with exclusive Q&As, interviews with top intelligence insiders, regular livestreams, ad-free listening, early access to episodes and live show tickets, and weekly deep dives into original spy stories. Members also get curated reading lists, special book discounts, prize draws, and access to our private chat community. Just go to ⁠⁠https://therestisclassified.supportingcast.fm/gifts⁠⁠ And of course, you can still join for yourself any time at ⁠therestisclassified.com⁠ or on Apple Podcasts. ------------------- THE REST IS CLASSIFIED LIVE 2026: Buy your tickets ⁠⁠⁠HERE⁠⁠⁠ to see David and Gordon live on stage at London’s Southbank Centre on 31 January. ------------------- Try Attio for free at ⁠⁠⁠https://www.attio.com/tric⁠⁠⁠ ------------------- EXCLUSIVE NordVPN Deal ➼ ⁠⁠https://nordvpn.com/restisclassified⁠⁠ Try it risk-free now with a 30-day money-back guarantee  ------------------- Email: ⁠⁠[e-mail]⁠⁠ Instagram: ⁠⁠⁠⁠⁠⁠⁠@restisclassified Social Producer: Emma Jackson Producer: Becki Hills Head of History: Dom Johnson Exec Producer: Tony Pastor Learn more about your ad choices. Visit podcastchoices.com/adchoices

For exclusive interviews, bonus episodes, ad-free listening, early access to series, first look at live show tickets, a weekly newsletter, and discounted books, join the declassified club at the rest is classified.com. This episode is sponsored by HP. Most people are not counter-espionage experts, but that won't stop them getting targeted by cybercriminals, seeking to extract their secrets. HP understands that approximately 4 in 10 UK businesses have reported cyber breaches in the past 12 months alone. That's why HP business laptops, desktops, and workstations bought directly on HP store

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Find out more about how HP can protect your business at HP.com forward slash classified. Podcast listeners benefit from a 10% discount on all business PCs, printers and accessories using the code T-R-I-C-10, Terms and Conditions Supply. Ensconced in his fabulous clericest suite, he spent his days holding court to a host of colonels, ambassadors, movie directors, and pals from the old days. Like some all-potent oriental Swami, he would with a wave of a hand dispense justice to all within his orbit. and deliver an unending stream of conflicting policy decisions that brought his subordinates

to the verge of collapse. While he pondered the problems of state, he doodled. At night, he would read as many as a half-dozen books at one sitting, jotting down excerpts that appealed to him. Brilliant, energetic, imaginative, and resourceful. He was unfortunately also selfish, petty, extravagant, and something of a racketeer. Well, welcome to the rest is classified. I'm David McCloskey. And I'm Gordon Carrara. And that is unfortunately, or fortunately, a description of how I like to spend my time at Clerges when I visit London. That was not a description of you. I was thinking, resourceful, energetic, imaginative, but also something of a racketeer. That's right. That's right. I don't know where you got this description of my time spent

in my fabulous. It's perfect, isn't it? Sweet to Clerges. but it's perfect and it's on the nose. That is in fact not about David McCloskey. Is that right, Gordon? I don't know. No, it was not David McCloskey. It was Walter Lord. That's Walter Lord, who rank over operations for the OSS,

the Office of Strategic Services in London, describing Wild Bill Donovan, the founder of the OSS, the forerunner of the CIA. But it is a great description, isn't it, of the character who we're looking at in this special two-parter for Christmas? I would not have thought that I would want to be described as something of a racketeer, but after reading that paragraph, I would be okay.

If this entire paragraph were just about me, I would be fine with that being the ending. But we did look last time, Gordon, didn't we, at the earlier life and the early career of Wild Bill Donovan, who is going to become the founder of the OSS. And last time we looked at how he got his nickname in the trenches of the First World War, his work for FDR as kind of an emissary, and importantly an emissary to Great Britain to determine how the U.S. might support the Brits during the Second World War. We looked at Wild Bill Donovan's early battles with J. Edgar Hoover at the FBI, and we actually left him at a proper American football game, didn't we not, Gordon, when he is receiving a phone call that will summon him to

Washington because the Japanese have just hit Pearl Harbor and FDR wants wildbill services in the war effort in an intelligence capacity. That's right. So he rushes to Washington. He gets to FDR's study around midnight. FDR's eating a sandwich. Interesting enough, the question FDR's got for him is, you know, were the Nazis in on Pearl Harbor?

It's a bit like the president going, who's behind this? And they agree probably not. And FDR says to Donovan something interesting, he says, it's a good thing you got me started on this. And I think what he's talking about there is the idea of needing a centralized intelligence agency. Because clearly they've had an intelligence failure at Pearl Harbor. And I think that's demonstrated the need for an organization. You know, there are going to be questions, of course, about who'd missed it and why and whether the Navy had missed some intelligence. But whatever it is, now there's this need, isn't there, for intelligence reports to be.

in some way coordinated and centralized and to get to the president himself. And, you know, FDR's going to want them delivered to his bedroom in the morning when he's reading his morning papers. I mean, this is the, it feels like this is almost the first time you get the president being briefed on a daily basis, you know, which is something you ended up involved in when you were at CIA, wasn't it? I think the modern, what became the president's daily brief doesn't really start until the Kennedy administration. But you do start to see. In this case, with FDR, certainly with Truman, the very earliest stages of the idea that there should be some kind of consolidated report that the president sees in the morning that

summarizes kind of what's going on in the world, right? And so you certainly don't have anything like the modern PDB in this delivery to Roosevelt, but you do, I think, start to see the idea that there needs to be some kind of system or process for helping the U.S. president understand what in the world is actually going on. in the world, which makes eminent sense. And Donovan, I mean, as we've seen from sort of just his personality at character, a lot of the ideas that Bill Donovan will push to FDR are not always sensible. Yeah, because that's the thing. He takes advantage of being this intelligence advisor to also start pushing more ideas and saying, we can do more aggressive action, we can

carry out commando raids, we can do, you know, sabotage behind enemy lines. He starts suggesting, expanding his team into something that does more than just gather intelligence, but also carries out these clandestine operations, which means a kind of new organization effectively. So they come up with this title, which is the OSS, the Office of Strategic Services, which I guess it's a great title because it's a classic intelligence agency title, isn't it? Because it's grand, but doesn't really tell you what they do, strategic services. I mean, what does that even mean? That's right.

Yeah. I think that impulse in the world of intelligence to create or to name a bureaucracy or the part of a bureaucracy and to actually reveal no information about it in the name is it takes some real skill. And if you actually walk around the CIA or go down to the basement floor and you look at some of the name plates on the doors. I mean, sometimes the doors don't literally don't say anything. It's just a number. But you know, in other cases, it'd be like the Office of Technological Resources and Support. Yeah, Special Activities Division. Special Activities Division. It's very hard to understand what they actually do. And I like the OSS name. It's better than the Silk Stocking Boys, which was the name of one of his fighting regiments in the First World War. So Roosevelt was going to agree June from 1942 to create this OSS, which immediately there's a bit of tension with the military, you know, how close is it going to be?

Also, of course, as we looked at last time, tension with his arch enemy at the FBI, Jayekah Hoover. One of the thing Hoover says is keep out of the entire Western Hemisphere, so including kind of Latin and Central America, because that is kind of FBI domain. It's kind of interesting, I find it. It's quite interesting in the modern world as well, that that is seen almost as domestic. Monroe Doctrine, Gordon. The Monroe Doctrine, yeah. It's your backyard. So Donovan gets this new job, and he's going to be kind of leading this new organization. And I guess the OSS is an extension of his own personality. He is a terrible administrator, but actually an inspiring leader who loves to be on the front line. Well, and I guess one of the first questions

that Donovan has to wrestle with is what sort of person do you recruit into this organization? And I guess the answer is obviously people who don't have any experience with anything that you're going to be doing. It's funny, is there? He basically goes for amateurs. I mean, glorious amateurs is what he calls them. What could go rock, right? Yeah, I mean, it's really interesting.

I mean, the way he decides to do that. I mean, he calls them the League of Gentlemen, his people. And there's social misfits, spoiled rich kids, military cast-offs. You know, that's how they're described. I mean, Douglas Waller's book, While Bill Dollivan, there's some great descriptions, just of the kind of unusual types of people he wants. And he also, he wants rule breakers like him, doesn't he? He says, I'd rather have a young lieutenant or lieutenant with guts enough to disobey an order than a colonel too regimented to think and act for himself. That's what he wants.

Well, again, I guess signs of the British influence operation that has been ongoing over Bill Donovan's heart and mind is that it reminds me a lot of the type of person that Mansfield Cumming was trying to recruit to join the early MI6, which were sort of naughty public school boys. I mean, this is kind of the same bottle, isn't it, that Donovan is deciding to replicate inside the OSS. I like this. OSS was said to stand for oh, so social. Because it was like, everyone's in the social register, right? Yeah, so they're all these upper crust socialites. You've also then got the kind of professors, you know, the idea that half of them were faculty meetings and half of them are cops and robbers. So you've got a mixture of kind of safecrackers with mafia ties and,

you know, professors from Ivy League universities, all all as part of it. I mean, it's a kind of crazy mix. It is. And, you know, it's interesting because the other thing I didn't, I didn't fully know was how bad everyone's eyesight was in the early OSS. They were called the Bad Eyes Brigade because so many of them were wearing glasses and had been rejected from, I guess, normal military service because of their eyesight. At its peak, the OSS employed over 13,000 military personnel and civilians. This is also interesting to me. 35% of its employees were women. Yeah. Quite an interesting role, including not just back office functions, but they were sending people out on the ground in operations as well. Julia Child was a OSS member.

Future CIA directors, Alan Dulles, shadowy spymaster, as we know, from Marj JFK episodes. Richard Helms, William Colby, William Casey, four future CIA directors, Hollywood figures, Hollywood director John Ford, intellectuals. It's kind of crazy mix, isn't it? There's your classic secret intelligence gathering, the kind of work we associate with in Britain, MI6, you know, sending officers undercover, you know, maybe posing his businessman to Casablanca or Istanbul. Then you've got research and analysis. Mini McCloskey's. The Mini McCloskey's, correct. Paramilitary, special operations. sabotage, dirty tricks, resistance groups. So that's like in the UK, SOE, special operations executive.

Then you've got operational groups, so uniformed commando-style units, the forerunner of US special forces in the army. So that's the equivalent of like, I guess what the SAS were doing in the UK and including in World War II. Then you've got black propaganda, psychological warfare, and you've got counterintelligence security and espionage. So it's everything, basically. And the, I mean, the morale operations, that there's, this is just one of the many crazy ideas that seemed to come out of the OSS. But there, there was a plan, which I don't think actually was, was implemented to try to expose Hitler to an insane quantity of pornography so that he would become a useless sort of leader. This was an example of the kind of ideas that are coming out of these sets, like sort of smoke-filled rooms inside the morale operations. operations department at the OSS. I mean, it does feel like a lot of the operations, they were pretty mad. I mean, he is dispatching agents on kind of crazy missions to scout routes around Tibet and

things like that. I mean, it's full of slightly reckless, slightly imaginative operations, I think. And it feels like lots of them kind of do go wrong. It's fast and loose, but they get things done. They're doing something. I guess that's the feel of it, isn't it? They are doing things. This was another great example, which came from Tim Weiner's book, Legacy of Ashes,

where he was describing how, I guess, at one case, Donovan sent guards to protect a captured German ammunition dump in France, and then they were blown up. I mean, so there are all kinds of, he said, and he mistakenly dropped commandos into neutral Sweden. I think there was another case of him losing a briefcase at a cocktail party that got turned over to the Gestapo by a Romanian. Indian dancer. So all kinds of, all kinds of sort of insane things were happening inside this

organization. But the other thing worth dwelling on is still this kind of really interesting relationship with the Brits. He remains this kind of anglophile. There are times when he is sharing more with the Brits than with his own military. And the Brits are sharing more, for instance, about code breaking with him than his own military shares with him. And he spends a lot of time in Britain as well. I do love the fact, as we heard in that opening quote, that he stays at Claridge's when in London, which we should say, David, is your favorite hotel. We talked last time about how me and while Bill were so similar, but this is what you two have in common, isn't it? Because whenever you're in London, I always find you in Claridge's, don't I? I'm always at Clerges.

I can be found at the Fumoir Bar, having wonderful martinis. Clareges is a very, very lovely place, Gordon. I'm now convinced that I must have been routed there. through some kind of social engineering to make me more amenable to the UK. Like, it's all part of a massive influence operation. We should say it because actually Claridge's plays an important part in the history of our podcast, doesn't it? Because it is actually where the two of us first met was breakfast at Claridge's. I mean, so if one was to be, as you said, conspiratorial about it,

one could think that one of us was recruiting the other Donovan style by running an influence operation by inviting the other clarets. I think you were there and I was visiting. So I like to think it was that way round. I don't know. I don't know who's running who in this operation. I think you take one look at this video and you got the guy in the velvet smoking jacket who definitely had the idea that we should spend $200 on oatmeal and have a wonderful,

have a wonderful breakfast at Claridge's. VAT not included in that number. But that was actually, it was where we first. met long before this podcast, long before this podcast actually was even an idea. Long before it was a twinkle in Gary Linnaker's eye, Gordon. You and I, you and I sat down and had breakfast. We were following in the footsteps of Donovan, weren't we? I need to find the room that he stayed in. Next time I'm visiting clerages. But London, I guess, becomes kind of a beating heart in many ways of the OSS. The London station for the OSS is absolutely massive.

isn't it? It's almost 3,000 people at one point. So it's like nearly 25% of the OSS's manpower is camped out in London, probably, you know, with coolers full of Fumoir Martini's in the office. Yeah, I know. I like this. One point he throws, Donovan throws a party to boost morale for the London staff. And one of the people there says, the injection of some 300 cocktails and untold bottles of scotch into our systems did the trick. But it's interesting. Because You know, we talked a bit last time about how Britain was pushing for OSS and backing Donovan and, you know, definitely trying to build its influence and relationship. But there's a bit of tension during the war.

I mean, because in that classic way, the Brits wanted the Americans on side. They want the OSS. They want Donovan there. But then when they actually start doing stuff, they're a bit like, hang on a sec, you want to drop people into France? That's kind of what we do in SOE or in other places. And, you know, you're just going to kind of blunder into our operations and it will get into trouble. And you kind of, it's described the OSS as kind of playing cowboys and Indians.

You can sense this slight kind of jealousy, slight friction as the OSS increasingly scale up and become doing what MI6 and SOE were doing. Yeah, be careful what you wish for, I guess, in your influence operations corded. The organization, though, really reflects the recklessness of the boss, because, I mean, Donovan, he's not sitting around in a desk. Is he during the war? I mean, you would think he's sort of sitting at his HQ in London or in D.C. and kind of making decisions and sitting behind a desk and talking to Roosevelt. But that's not really what he's doing, is it. Right from the start, he is out there in the field. He is taking every opportunity he can to get into war zones. He would alarm his own staff and the Joint Chiefs because he wanted to see his guys in action. And I mean, his own special assistant, Fisher Howe, in an interview, described his boss as iriscipline. responsibly adventurousome. He was doing things that no head of intelligence should have been doing. I mean, there's one great story about the way he operated, because one of the things in the

research and development wing at OSS they were doing was doing gadgets. And under this guy, Stanley Lovell, who Donovan called Professor Moriarty, you know, he's developing different kind of gadgets. Amongst other things, explosive powder made to look like flour, which could be needed and baked into bread, which was codenamed Aunt Jemima for some reason. And during one test, explodes and sends shards of steel close to Donovan's head. And the lab is also developing female sex hormones, which they want to inject into Hitler's food. They've got K-pills to knock people out, L-pills, cyanide pills, truth drugs, which they're going to try out on people, looking at biological weapons. But then one of the things that they try and develop is a silenced pistol to use

for assassinations and covert actions. And by 94, they've got a breakthrough by fitting a silencer to a pistol. Donovan brings it to the White House, because he wants to show it to FDR. FDR's busy, you know, in a meeting. And Donovan thinks to himself, well, this is my chance to show off how good these silences are. So he, in the White House, he sets up a sandbag and across the room fires 10 rounds into the sandbag in the White House using this silenced pistol. And then, you know, FDR finishes his meeting, comes in the room, and Donovan pulls out this sandbag and goes, hey, look, I just fired 10 shots into this sandbag. And no one noticed because our silencer is so good. I mean, he's literally shooting guns in the White House.

Well, in FDR, you might think, well, you know, as the president sort of angry about gunfire in the White House. And it's the exact opposite, isn't it? I mean, FDR is actually so impressed that he decides to keep the silencer. And it is actually now on display at his presidential library in Hyde Park, New York. So job well done, Wild Bill. Job well done. Way to read the first customer there. That's perfect. Yeah, exactly. I don't think I don't think Clarence CIA directors would try that these days.

Well, maybe. I don't know. But this idea if he wants to be where the action is, D-Day is approaching 1994. It's so funny because all the senior military specifically say Donovan must not take part. in D-Day, like, you know, the fact they have to say that and give orders not to do it. And yet Donovan is still like, I'm going. Douglas Waller in his book on Donovan, you know, talks about Eisenhower agrees that there is no way that America's top intelligence officer should be doing the D-Day landing. On the beach. We're not talking about coming in later. On the beach.

No, no. He's trying to get there on the beach. So Donovan is kind of going around. And even though he's been ordered not to do it. He turns on his charm and kind of goes round Navy friends going, can you get me onto one of the ships? And so by D-Day, June 1944, he is off Utah Beach in Normandy as the invasion comes. He can't get on immediately. So eventually, within hours, he's basically commandeering a boat, straps on his helmet, pins on his Medal of Honor, climbs down a rope onto a launch and tells the kind of helmsman, get me to the beach. And then it looks like he might have to swim the last 20 yards, but then he hails one of these amphibious trucks, which is like a duck to get him to land. Do you know, I was reading about these ducks. Do you know these duck

boat things, which are kind of both boats and they can go on land? Have you seen those? Oh, sure. Because they used to have them as tourist boats. They have them in the States, too. Yeah, they used to be tourist boats on the Thames. You could go on one of these duck boats. And I was looking it up. And I was thinking, well, are they copies? They were like, those were the actual World War II duck boats that they just kept. So it's not even the same type. It's just an actual boat. It's not even the same type. They're actual World War II duck boats. And then they're taking tourists around the kind of Thames in London. So, you know, Donovan gets onto one of those. And so he runs into some trouble on the beach, though. Yeah, because then four German

Messerschmitts strafe him on the beach, rolls off, uses the duck for cover. he's there with his London station chief from OSS, who kind of falls on him and draws blood. The pair of them start walking miles, and it's just the two of them. This is America's top intelligence officer, and with his head of station in London, walking basically a day after D-Day through the war zone, at one point they enter a field, enemy machine guns open up from a hedgerow, and then Donovan says to David, his assistant. You understand, of course, David, that neither of us must be captured. We know too much. Donovan is saying we're going to have to use our L pills to kill us if we're captured, which is kind of obvious.

And then I love this fact. You know, his station chief says he hasn't got his. And Donovan says he's got two. And then he realizes if he's left them at clarages. Well, who hasn't left their suicide pills at clearages before, Gordon? I mean, it's just, you know, it's just something that happens. I'm always leaving them behind and putting them, you know, on the bathroom counter. But, I mean, Donovan is kind of thinking that someone might get killed at Clarges, right?

Because he says, you know, never mind, you know, we could do without them. But if we get out of here, you must send a message to Gibbs, the Hall Porter at Clarages in London, telling him on no account to allow the servants in the hotel to touch some dangerous medicines in my bathroom. Could you imagine? I mean, that's what he's worried about. He's in this water. worried about someone taking his pills. And then, and then they still think they're going to get shot. And Donovan says, I must shoot first. And, you know, David's assistant says, you know, yes,

but we can't do much against the machine guns with our pistols. And Donovan goes, no, you don't understand. I mean, if we're about to be captured, I'll shoot you first. After all, I'm your commanding officer. So he's basically saying, you know, with our pistols, we're going to take each other out. But luckily, I think at that point, Allied planes and artillery open up and they escape. And And eventually they find a command post. But, you know, that is pure Donovan, isn't it? And there was zero logic to doing any of this, right? I mean, there's no value for DOS, period, in having Donovan on the beach.

But it makes for a great story, and it adds to the lore. I mean, there was this great line from David Bruce later on about Donovan. And on D-Day, Donovan apparently told David Bruce that he had arranged to be buried at Arlington Cemetery and asked Bruce if he had done the same. And when Bruce said no, Donovan replied, you should get a plot near mine, then we could start an underground together. This was one of these great Donovan sort of exchanges where you wonder how much of it's true and how much of it's not. And it all sort of adds up to this, you know, because this is a story that an aide of his is telling three decades later about the man. The legend. Give you a sense of, yeah,

the legend that has built up around him. Yeah. So as the war comes to an end, you know, he's still coming up with these wild plans and he wants to send out 22 assassins to kill senior Germans, including Hitler and Goering, but just before they plan to do that, Donovan reconsiders, you know, thinking it would be a mistake. So the war is coming to an end. I mean, there have been amazing operations in Europe, people behind enemy lines, also a lot of really interesting stuff in Asia as well. But now, with the war coming to an end, the battle is not over for Donovan because he's going to fight the biggest battle, I guess, in his career. And it's going to come in Washington. Oh, and maybe there, Gordon. Let's take a break.

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And I guess Gordon, sadly, for William Donovan, wow, Bill, the war is over. This actually is a very, very sad moment for him. and eventually, I guess, for the OSS. The question is, what's going to happen next? And even as the war is drawing to a close, in the kind of period up to the end of it, Donovan is spending his time, yes, in London, in his kind of command center in Clareges, which I love the fact, takes up an entire floor of Clareges, an entire floor. It would be very expensive today.

It would be very expensive today. As you'd know, he's thinking, what happens after the war? And November 1944, he sends a memo to Roosevelt outlining what became known as the Donovan Plow. And this is a proposal for a permanent civilian-run worldwide intelligence service, a central intelligence agency for the president. Makes sense, but the problem is, Donovan has a lot of enemies, doesn't he? And they're going to go for him. And I guess top of that list is going to be Hoover and the Phoebes. Yeah, the Thebes really don't like it

And you look at it during the war They've been all of these battles Hoover is also trying to build his own intelligence service around the world So Thebes are going out to embassies to kind of track threats against the US But also secretly to kind of build Hoover's network Also, Donovan is going, he goes to Moscow And he gets an agreement to set up intelligence liaison With the NKBD, the forerunner of the KGB

You know, both of them are trying to do that But then Hoover is also unhappy about that because he doesn't want more liaison and Soviet spies running around, and he's going to spread rumors that the OSS is full of Karmies. Hoover's got the kind of gossip about the private life of Donovan, and he's kind of spreading that gossip. And Hoover has got his own plan. You know, Hoover wants the FBI to basically take charge of a peacetime intelligence service, which is not just domestic, but throughout the world, with the Navy and the military just supporting it in war and in theaters of war. So you can sense the kind of the intrinsic bureaucratic as well as personal

tension between those two sides. And I guess it's not just tension with other civilian intelligence services or little pockets of other federal agencies that are civilian that have an intelligence capacity, but it's also with the Pentagon, with the military. Because, I mean, Donovan, he's actually had more of a struggle getting information from some parts of the military than he has from, say, the Brits, and he's got that really consequential rival in General Douglas MacArthur, who, I guess, had more or less kept the OSS or tried to keep the OSS out of the Pacific theater during the war. And it's interesting as well how far some of the kind of tension and resentment with

MacArthur goes back to World War I. There's actually tension back to the very start, one of the battles in World War I that Donovan is decorated for. MacArthur is also involved in that. And, you know, there's some question about whether Donovan resents MacArthur for not supporting him in battle at Landre at Saint-George, but others thinking that MacArthur is jealous and thinks that, you know, Donovan is a kind of reckless operator and is also jealous that Donovan got the Medal of Honor and he hadn't.

So you can see, actually, with a lot of the military guys, they just don't like him. The military are going to, particularly the army, going to draw up this 59-page memo, which is going to really lay into Donovan and OSS. I mean, I guess there's also the accusation that Donovan, Donovan's organization has been penetrated by the Brits, right? Yeah. And that's another one of the kind of smears that his rivals put out against him is that basically he's too close.

He's virtually owned by the Brits. And I guess he's also totally dependent on his relationship with FDR. And that obviously is going to be a weakness, but throughout the war it's made a lot of people very resentful of Donovan's influence over the president. Yeah, and I think there are lots of resentments, you know, in rivalries, and they're going to leak his plan to the press. And then there's going to be the classic sensationalist headlines that the plan is to create an American Gestapo under Donovan, which is going to pry into everyone's lives. It's going to be a kind of political secret police. All of this is making it

hard for FDR to support it. It's interesting because with some of those leaks, Donovan thinks, well, it must be, you know, Hoover who's done this. There are some claims. It could have even beat FDR and people around him as well. They were also trying to kill the plan and not have their finger prints on it because actually they don't, they don't actually want this guy to be running it either. So he's hitting some pretty big headwinds. Do you know who Donovan had breakfast with the morning after he discovered FDR had passed?

Was it a shadowy British spymaster? It was a shadowy future American. By-master. It was not other than William J. Casey, who will lead the CIA under Reagan and who at that point is an OSS officer. And Casey and Donovan are breakfasting. And this news, obviously, the FDR has passed, has just come to Paris. And Casey asks, what do you think it means for the organization? And Donovan says, I'm afraid it's probably the end. And he's so right. And he's so right. He's so right. Because FDR's gone. His protector's gone. And the new president, Truman, he doesn't know that. much about intelligence. Famously, he didn't know that they'd been developing the atomic bomb, which is so... He's a haberdasher. He's a haberdasher from Missouri. Yeah. And so Donovan had relied on that personal kind of relationship and friendship with FDR. And now Truman is looking at this guy, who is this kind of Republican kind of reckless guy? The first meeting, I think,

is really chilly, just goes on for 15 minutes. And of course, Truman is smart enough to think, I don't want a spy service run by either Hoover, Jay Edgar Hoover, or Donovan. I don't want either of these guys to be running my global spy service. Well, and I guess then, sadly, the OSS is formally shut down because on September 20th, 1945, I mean, really just weeks after the end of the war, Truman signs Executive Order 9621, which dissolves the OSS components get scattered about. I do love this, though. So there's obviously a frantic shutdown here, right?

Sources are terminated, operations are stopped, but what do you do with all the paperwork? And Donovan basically creates 131 roles of film that he then copies of these documents, pictures of the documents, and he sends him to his law firm so he can hold on, hold on to as many files as possible, maybe in the hopes of making a comeback. Yeah, and it's really interesting, isn't it? Because he does spend the next few years thinking he's going to make a comeback. I mean, his first job, he's in it, after this kind of dissolution, he's sent to the Nuremberg trials as an assistant to the U.S. chief prosecutor. But what's interesting is he doesn't give up hope that he will return as the kind of spymaster.

Because, of course, you know, Truman has deliberately decided, I don't want this spy service run by Donovan and Hoover, but he quickly realizes, I am going to need a central intelligence agency. You know, I'm going to need that. So within a year or two of dissolving OSS, he has created. the central intelligence group and then the CIA, isn't he? Yeah, it's, I guess, kind of ironic and probably was very frustrating to Donovan because it's more or less what gets created is exactly what Donovan had suggested, right? It's a central agency that's part of the executive branch that reports to the president. It is going to inherit a lot of OSS veterans because they were part of the wartime spy service

and have that experience. It makes perfect sense. But not Donovan. He's out. He's still kind of. seems to be hoping that he might come back. So 1952, he's campaigning for Eisenhower to win, the Republican, hoping that therefore, you know, when Eisenhower wins, Donovan might get appointed a CIA director. And instead, Eisenhower chooses, I mean, it must be really painful because he chooses one of Donovan's subordinates, Alan Dulles, to be the head of the CIA. I mean, more of a bureaucrat, more of a kind of political operator, I guess, than Donovan. but must have been pretty disappointing.

Well, and then Donovan gets sent to Thailand, which I find to be a very random sort of coda at the end of the Wild Bill Donovan story because Eisenhower appoints him as the U.S. ambassador to Thailand. He serves there from 1953 to 54, but I guess at this stage, his health is really starting to decline. I think he was a big fan of drinking and also a big fan of eating steaks.

And those two things, I think, do catch up to you over time. So he's showing signs of dementia and sort of overall physical deterioration by the mid-1950s. Yeah, so he ends up at Walter Reed Hospital in Washington with dementia. It gets lots of visitors from his OSS days. Eisenhower visits him and later tells someone that, you know, Donovan was the last hero. But then I love this detail. You know, he often tries to escape his bedroom at the hospital and has to be coaxed back by the nurses.

And he's reliving those World War I battles. And he's reliving kind of D-Day and being on Utah Beach. he's reliving flying over Burma, and he starts to see these visions of the Red Army coming over the 59th Street Bridge and into Manhattan. And in his last mission, he's kind of fleeing the hospital and walking down the street in his pajamas to kind of contrompt the invading Red Army. But he's approaching the end, but still living out this kind of fantasy life, I guess, as this great hero, which he was in many ways. Must have been really rough on the nurses. This sounds like a terrible patient to have

with these insane kind of visions and stories. But, you know, he passes at the age of 76 on the 8th of February 1959. And I think this is kind of remarkable because he never led the CIA, as we said up front. But when he does pass, the CIA sends a cable out worldwide to all station chiefs saying, quote, the man more responsible than any other for the existence of the Central Intelligence Agency has passed away. Yeah, it's quite a tribute, isn't it? Here's an extraordinary character. I mean, you can argue about how successful the OSS was.

I think a bit like Britain's SOE in the war, it made a lot of noise and, you know, distracted a lot of Germans, how strategically successful the Office of Strategic Services was. I think, you know, is perhaps a kind of open question, I think it's fair to say. But that's kind of not the point, is it, with Donovan? Yo, don't you think it basically had no impact, though? I mean, that's what some people say, isn't it? I think Helms, you know, who later runs the CIA, says, I don't think it made any difference or much difference. There were some successes, but, you know, he says it was not a howling success as an organization.

I mean, I mean, maybe that is true. Individually, you know, did this operation shorten the war by this much or that much? I think some of these resistance groups and sabotage groups, they helped. They did play a role, though, I think, in kind of supporting morale and encouraging resistance on the ground. Did they change the course of the war? bit less obvious, I think, when it comes to the kind of paramilitary groups, I think. I mean, what certainly is enduring, though, is the legacy that Donovan and the OSS created, and I think really bequeathed to the early CIA as it's developing as an organization

in the late 40s and early 50s that kind of this, you know, the height of the Cold War. I mean, Donovan's character and personality were sort of deeply imprinted on the way the organization worked. And I mean, the number of CIA directors who came out of the OSS, I think is really a static. This wartime experience really shaped the first three, four decades of the agency's life and existence. And that was all built, you know, the personality cult makes it sound too creepy and weird, but it's all built around the personality of Wild Bill Donovan. Yeah, I think that's absolutely right, isn't it? Because I think the combination of different elements into what become the CIA and are there in OSS, again, are quite unique, and it's

different from MI6, because I think MI6 is really quite single-mindedly an intelligence gathering organisation. Paramilitary stuff is it there in SOE in Britain and in the SAS, whereas in US, it's all there in OSS under Donovan, because of his personality, because of his military background, because of what he's into. And you see that kind of go into CIA. And that is also one of the differences between CIA and MI6 today, you know, is that the CIA has this kind of paramilitary wing. He's more interested and more willing and greater history of going into kind of combat operations and being the kind of tip of the spear in a way that MI6 has never quite done, I think. So I think that's one of the interesting, you know, differences there. I

I mean, other kind of bits that come out of it, I think bureaucratic warfare, you know, the battle with the Thebes, you can see right from the earliest days, you know, the FBI-CIA rivalry, which is definitely there for decades onwards. You can see the roots here, can't you, as well as some of the other tensions that exist. And, of course, the ability of the Brits to happily manipulate the Americans. Another great legacy of Donovan's time. It is, it is. I don't think I understood the full extent of how involved. the Brits were in shaping the idea, the American idea of a centralized intelligence agency. And it is also, you know, I think there's a big question in my mind, Gordon, around we are now in a new century, right, from the creation of the original CIA back in 1947.

and you kind of think, okay, well, I think probably somewhere around the 80s, we sort of lost a lot of the kind of cultural connection between the age of Bill Donovan and the OSS and the sort of CIA was really gone by the time you get into the late Cold War. You know, the CIA had become something much different. But you wonder nowadays with, I think maybe the need to reshape the agency into something different, given the challenges from. China, given the challenge of kind of reimagining a lot of the tradecraft, given, you know, sort of the technological environment around us, which, by the way, is something we'll be talking about on a couple episodes next week with a very special guest. Do you have a system where you can have a founder like Bill Donovan who can imprint the organization in such a strong way? Like, is that even possible anymore? Or have we just moved, have we moved beyond the ability of of a single-minded, really colorful, somewhat deranged person to kind of remake an intelligence

agency in his or her image. I don't know. I think maybe it's not possible anymore. The scale is just so, so different. Yeah, they're bureaucratized in a different way that I just don't think you could shape it in that same way. And I certainly can't imagine current chiefs being like Bill Donovan or surviving. You know, you've got to be a bureaucratic player. You've got to be a bureaucratic player. going to be a manager. You've got to know how to play those games in a way that Donovan didn't in order to kind of survive now. I think, you know, he was that kind of wartime leader. He was the right leader of an intelligence agency at wartime, given his record, but not necessarily one for the Cold War and the relative piece that came afterwards. You required a kind of different

type of intelligence. You can see Donovan wasn't the right man for that. It did need to move on and you needed someone different for him. So, yeah, I think it's a really interesting kind of question about leadership and culture and spy agencies. Well, yeah. And his legacy certainly does live on. I mean, there's, you know, Casey who was having breakfast with him the morning that found out that FDR died. He commissioned a statue of Donovan, which is up at Langley. And I think that tip of the spear mentality that Donovan lived and breathed, I mean, lives on. I mean, the logo for the CIA's Directorate of Operations today is tip of the spear with a gold spearhead and a black background. So you can still see that sort of legacy of Donovan.

of in just the way the agency sort of attempts to portray itself and talks about itself today. And I like to think you're living out the legacy, David, staying at Claridge's in London. I'm doing my small park, Gordon. You are living the legend. I'm doing what I can. I'm staying at Clarages. I'm in the middle of a vast goalhanger-funded influence operation to affect my very heart and mind. I'm just doing what I can. Live in the legacy of Wild Bill. That's right. So there we go. That's right. There was the story of Well, Bill. Just a reminder that if you are a club member, if you're a member of the Declassified Club, we have got a very special episode, which is the best of the Rest is Classified in 2025,

which you can list to it. If you're not a member, why not? It's Christmas time. Spread some Christmas cheer. Join the club at Restlessclassified.com. It's not too late because this episode is going out on Christmas Eve. So, you know, it's Christmas Eve. There's still time to stuff a Restis Classified membership for your nearest and dearest into

your Santa sack and give that to them for a trip down the chimney tonight. That sounds wrong. We should also say that these will not be the last episodes of the year. We will return in that horrific week between Christmas and New Year's where all seems lost. And we will be back with some final episodes next week to kind of close out 2025. And as I said, we'll have a very special guest who will be with us to talk about how human espionage is changing in a world of phones, cameras, sensors, cheap storage, and AI. So do tune in for those. I think we've also got some tickets remaining for our live show in London

on 31st of January, that last few. So be one of the lucky ones to get that. Go to the rest is classified.com and grab yours. If not, Merry Christmas. Ho, ho, ho. And ho, ho. We'll see you next time. See you next time.