Wooster: What exactly does the term "Master spy" mean in this part of the world, anyway?
Krosp: Hmm "Sneaky gossip-monger"?
Wooster: That explains so much.The Handler of handlers, moving spies about all over the world. Often The Chessmaster. Typically he is cold and dour, though sometimes he has a heart of gold. Easily made a villain though sometimes at least an antihero. Few main protagonists are Spymasters. The reason, of course, is that the hero has to be where "the action" is. Which is seldom in an office. Compare Knowledge Broker for when the Spymaster is operating freelance.
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Anime And Manga
- In Shoukoku No Altair, Süleyman is the chief of spies for Türkiye. He's constantly travelling to keep in touch with the spies stationed in each country of Rumeliana and recruit other potential spies. And he works under Zağanos Pasha, who is their superior and tells them what it is they have to do directly.
- The protagonist (of a sort, though he's not the POV character) of Joker Game is Lt. Col. Yuuki: The Chessmaster, Magnificent Bastard and Spymaster, all in one.
- The League of Extraordinary Gentlemen features Mycroft Holmes (Sherlock Holmes' brother), then later Harry Lime from The Third Man as 'M'. Following on from the original 'M': James Moriarty.
- Amanda Waller and Sarge Steel have both filled this role for the U.S. Government in The DCU.
- Nick Fury: Director of S.H.I.E.L.D. takes a very hands-on approach to this job. He's pretty much the Memetic Badass of the Marvel Universe.
- He's succeeded by, among others, Maria Hill, Daisy Johnson, Norman Osborn (who replaced S.H.I.E.L.D. with H.A.M.M.E.R.) and the below mentioned Steve Rogers.
- Pete Wisdom, while not the head of his agency (at first - by Captain Britain and MI13, he's taken the job), serves as the closest thing to a counter-part Nick Fury has in MI-13, Britain's paranormal agency, and is similarly hands on.
- Recently, Steve Rogers served his country in this manner upon returning to life, operating as a Nick Fury-esque spy.
- Recurring Iron Man foe Spymaster lives up to his name, with his own organization (the Espionage Elite), as well as being a master industrial spy himself.
- Moff Nyna Calixte a.k.a. Morrigan Corde from Star Wars: Legacy.
- Paul Crocker, Director of Operations, from Queen and Country. Very much a Spiritual Successor to Neil Burnside.
- The Red Skull more or less had this job when he was with Those Wacky Nazis.
- The Pieces Lie Where They Fell: Memorizing Gaze, Secret Protector of the Hidden Guards, is officially identified as one of these in the sequel Picking Up the Pieces - the Hidden Guards are Equestria's secret intelligence division, who investigate potential threats to the nation. He even keeps Guards in his fellow Captains' headquarters to keep an eye out for other potential infiltrators.
- What About Witch Queen? has two: baron Hakan Madsen is the Royal Spymaster of Arendelle (while, at the same time, being the commander of Marines) and colonel Glenn Hunter holds the same position in Weselton. Madsen is more of a heroic example, and Hunter appears villainous, or at least Jerkass.
- In Bad Future Crusaders, Featherweight serves as this to Queen Twilight, being in charge of the Changeling spies deployed around Equestria. He even refers to himself as "the Queen's ears" at one point.
- In addition to Nick Fury, Child of the Storm also has Peter Wisdom a.k.a. Regulus Black (Fury's protege and counterpart at MI13), Lucius Malfoy (who served this role for Voldemort), and Loki (who felt, as part of his reformation, that this was the best way to serve Thor and Asgard).
- Loki, being the Magnificent Bastard he is, understands the problem of training and planting spies throughout the world would be incredibly difficult, even more so if he wished to avoid the attention of other spymasters. So he doesn't even try: Instead, he uses taxi drivers, cleaners, and the homeless as informants. All three groups are already everywhere and hear much more than people think. So not only can he set up an invisible network everywhere, he can actually help the less fortunate at the same time by paying for information.
- Ghosts of the Past adds General Aleksandr Lukin as the head of the renewed Red Room.
- Summer Crowns:
- Orton Merryweather becomes Master of Whisperers to King Stannis.
- As Lord Intendant, Tybero Istarion serves as this to the Dragonhunt after the Second Sons are reorganized to be their Secret Police within Myr.
- Varys "the Spider" in A Song of Ice and Fire is the Master of Whispers (and occasional private businessman on the side) and likes saying he gets his information from his "little birds". But, as you can tell from the title of the position, there have been several such spymasters advising the Iron Throne over the centuries, some more renowned (and faithful) than others. Take Brynden "Bloodraven" Rivers for one infamous, yet faithfully ruthless, further example of the breed. And, Not-a-Maester Qyburn for another.
- "Control" in the George Smiley books by John le Carré and his Soviet counterpart "Karla". Smiley himself at times, especially in Smiley's People. Note that "Control" is based on "C," the head of the SIS, also the basis for "M".
- Javelin from The Belgariad is the head of Drasnian intelligence (the best spy network in the world) and is also the direct handler of Hunter, a spy whose identity is known only to him. As a (borderline anti-)heroic version of The Chessmaster, he can seem a bit ruthless at times—in the sequel pentalogy, he even orders the crucifixion of his own niece as one of the cultist traitors captured during a city siege. She's actually the current Hunter, and it's all part of a plan to infiltrate the cult by letting the cultists' rescue attempt succeed.
- Donald Hamilton's Matt Helm novels. "Mac" (Helm's boss).
- "M" (Sir Miles Messervy, later Admiral Hargreaves, then Barbara Mawsley) of MI6 in the James Bond novels and movies.
- In Lois McMaster Bujold's Vorkosigan Saga, Simon Illyan is the head of ImpSec the spying and counterspying organisation of Barrayar. He also plays the role of Da Chief to Miles.
- Illyan's predecessor, the legendary Captain Negri, was this in spades.
- Rufus of the Blackford Oakes series by William Buckley.
- Dr. Harold Smith from the Destroyer qualifies because he can take on this role, although in most of the novels he rarely is seen doing this, he does this in cases he doesn't need Remo's skills.
- Count Sigismund Dijkstra is the Spymaster of Kingdom of Redania and one of the principal players in Andrzej Sapkowski's The Witcher series.
"If Dijkstra says it's midday, but it's pitch dark on the street, start to worry about the sun's fate."
- And in the game based on them the fence Thaler is actually head of Temerian intelligence and the secret police.
- Tortall Universe:
- Sir Miles of Olau is the spymaster for Tortall—at least, he's the one everyone knows about. The primary spymaster is Alanna's husband George.
- George trained his daughter Aly, and she puts the skills to good use in the Daughter of the Lioness books when she works for the raka in the Copper Isles. She eventually becomes the rebels' spymaster, takes down the Rittevons' own spymaster, and becomes the spymaster for the country when the revolution succeeds.
- 1632 series:
- Fransico Nasi takes on the role as spymaster for the newly arrived Americans by the end of the first book of the series, building on extensive information networks spread throughout 17th Century Europe.
- Duchess Grendine from Terry Mancour's Spellmonger Series. She maintains a sinister alter ego known as "The Mother", the head of the castali intelligence apparatus known as "the Family".
- Father Mutio Vitelleschi, Superior General of the Society of Jesus, pretty much serves this function for Pope Urban VIII.
- "The Spider," a.k.a. Dona Angiavesta Vorchenza, in ''The Lies of Locke Lamora. The secret head of Camorr's Midnighters, an order of secret police that reports to the Duke himself. It helps that the Spider goes unnoticed because she's a seemingly harmless old widow.
- At the end of the book, the position is handed off to two people, Don and Dona Salvara.
- Thufir Hawat in Dune. One of the few intrigue tales that shows The Spymaster's perspective.
- Salthar in the Spaceforce novels is head of the Tayshak, the 'semi-clandestine' department of the Taysan Court which conducts internal and external espionage. Given that Taysan culture is squeamish about all such things and recruits only misfits and functional sociopaths as agents, Salthar finds himself in charge of a real rabble of potential rebels and seems to have difficulty in managing them.
- Subverted The Wheel of Time, where Pedron Niall's well-known spymaster, Omerna, is an incompetent decoy, and all the spying is actually done by his secretary.
- Moghedien plays this role for the Forsaken. She's not that impressive power-wise by their standards and knows it, but is incredibly sneaky and treacherous (she's named for a kind of tiny but deadly spider from the Age of Legends). Her tendency to underestimate the "primitives" of the current Age, however, landed her in hot water on several occasions and ended up getting her severely punished by her superior, Moridin.
- Each of James H. Schmitz's milieus has a spymaster:
- Major Hogan from the Sharpe series. Nominally an engineer, but, according to Sir Arthur Wellesley "a man with very diverse duties".
- Narses and Irene in Belisarius Series.
- Irene deserves special mention because she is amiable and rather perky rather then being dour which is the normal personality for this kind of character.
- The Dresden Files
- Bob and other knowledgeable agents identify Archangel Uriel as God's personal spymaster and "black ops guy". He is, however, limited by not being able to affect a person's freewill. He cannot give information or knowledge that would otherwise change a person's choice, but rather give them help for a choice already made. Even with this severe limit on a being who states he is capable of destroying galaxies, he knows humanity well enough that a tiny nudge at the right moment will hit three or more birds with one stone.
- Nicodemus Archleone is the bearer of Uriel's opposite number, Anduriel, who has the title "Master of Shadows." He was Lucifer's second-in-command during the War on Heaven and cast out from Hell into a Coin to terrorize earth. Befitting his name, Anduriel can spy from anything that casts a shadow unless it falls within a protected domain.
- As befitting his mythical persona, Donar Vadderung aka Odin is also one of these, and implied to be even better than Nicodemus. Doesn't hurt that he also visits loads of families every Christmas night, in his alternate form as Santa Claus.
- Imperial Inquisitor Meng Ki in the Judge Dee novel ''The Chinese Lake Murders".
- Angleton from The Laundry Files. Notably, it's not his real name; Bob notes that only he could have gotten away with using James Jesus Angleton as a Mom De Guerre.
- In Marque And Reprisal, the second book of the Vatta's War series, it is revealed that Aunt Gracie was a skilled spy, going so far as to bug the President's office when it seems he might have something to do with the coordinated attacks against the Vatta family and to scout out the best places for a sniper to take a shot at their home from, booby-trapping those spots with diseased ticks. For bonus points, in the first book, Trading In Danger, this character was explicitly and dismissively described as The Family Spy.
- The Big Bad of the first four books of the X-Wing Series is Ysanne Isard, Director of Imperial Intelligence, the de facto head of the Empire. Her fearsome skill at breaking captives down into Manchurian Agents, and the ruthlessness shown when she betrayed her own father to assume his position, have earned her the nickname "Iceheart." Opposing her is the good guys' own Spymaster, Airen Cracken of New Republic Intelligence, known and feared as "the Kraken" by Imperial operatives.
- Pretty much a stock character archetype in BattleTech fiction — whenever the narration focuses on the setting's movers and shakers (or even just a commanding officer worried about operational security), it's usually a pretty safe bet that their respective spymasters won't be far away. In fact, the main plot of the now-classic Warrior trilogy pretty much revolves around Justin Xiang Allard, son of the spymaster of the Federated Suns, becoming first an arena champion, then an intelligence asset, and finally a spymaster in his own right for the Capellan Confederation.
- In the Tolkien's Legendarium, readers frequently interpret the role of Radagast the Brown as a spymaster for the Istari and White Council. His gimmick being that he would use animals (such as birds) as his eyes and ears. He is also said to be a master of shapes and hues, possibly indicating that he is a Master of Disguise. This is frequently offered as a proposed reason for Radagast's overall reclusiveness and seeming inactivity during the War of the Ring as opposed to Gandalf's conspicuous involvement and Saruman's treachery. Tolkien appeared to be inconclusive regarding his original claim that Radagast failed in his mission (he really only says that "Only Gandalf stayed true to his original mission" and it is a given that Saruman can definitely be said to have failed). Gandalf's high respect for Radagast does not seem to mesh with the any notions that Radagast was neglecting his task. Readers tend to speculate that Radagast may have been doing the job for which he was sent and that not all of the Wizards were intended to employ the same methods or even necessarily work openly or together. Radagast is occasionally credited with the unexpected appearances of the Eagles in various instances, as well as the Thrush who delivered Bilbo's message to Bard in The Hobbit. As a spymaster, Radagast would understandably be very low key and indirect by necessity.
- Louis Goliath of Doctrine of Labyrinths. Although he's perfectly willing to use hideous methods, from physical mutilation to Mind Rape, to further his ends, he never does anything spitefully or without considering the consequences— indicating a detachment that seems to scare Mehitabel more than his atrocities.
- Jules Sevier in Amante Doree from Somewhere Beneath Those Waves. He's a particularly nasty example, since he deliberately sets up one of his own spies in order to discredit an honest investigator.
- Earth's spymaster in Isaac Asimov's Nemesis has so much dirt on the politicians in charge that if he wants something, he can get it. He is integral to allowing Earth's hyperdrive project to succeed, simply because it plays to his obsessions and he has the influence to get the politicians to keep throwing money at it despite the need for secrecy. He also runs the best intelligence agency in the Solar System, for a variety of reason starting with the fact that Earth has a lot of people of pretty much any ethnicity and ending with the fact that the Settlements looks down on Earth and so tend to have something of a blind spot when it comes to Earth's advantages.
- Bob Ritter from Tom Clancy's Jack Ryan novels is the CIA's Director of Operations, which means that he's the man who manages all of the CIA's human intelligence assets.
- In the Safehold series, nearly every member of royalty we meet as The Good Chancellor and spymaster or their equivalents as their closest confidantes. Among main characters Prince Nahrmahn is made the Imperial Spymaster for the Empire of Charis, largely to focus his love of Machiavellian plotting to positive ends and because he's really really good at it.
- In The Collegium Chronicles, Herald Nikolas acts as Valdemar's spymaster, in addition to his public duties as the King's Own Herald. No one suspects him of running an intelligence ring on top of his full-time job as personal adviser to the monarch and duties as a father. The protagonist Mags is trained as a spy by Nikolas, joining him undercover as a pawnbroker and fence in the capital city's poorer districts. In the sequel series The Herald Spy, Mags begins to set himself up as Nikolas's successor, inheriting Nikolas's agents in the city and establishing his own, while Nikolas shifts his focus to the kingdom at large. In the reign of Queen Selenay several hundred years later, this duty has been passed down to Herald Alberich, in addition to his own public job as Weaponsmaster.
- From A Symphony of Eternity there's High Princess Monas’ Zulanasai de Harkonian, nicknamed ‘Cainblessing’ by her ‘allies’, and the ‘Fire Princess’ by her ‘enemies’, the most feared being in the Empire, if not the Galaxy itself. Besides being a Lightning Bruiser, she's such a great Spymaster that she's able to take informaion than may seem trivial to anybody else, but she can use it to discover the enemies greatest secrets.
- In The Zombie Knight, Ivan "the Salesman of Death" is the spymaster for the Morgunov Abolishers, as well as being involved heavily with their revenue operations and negotiations with client states. On top of that, he's a fearsome combatant in his own right, as is anyone in the Abolish or Vanguard inner circles.
- In The Traitor Son Cycle, Kronmir is a spymaster for hire, who creates and maintains networks of spies and assassins wherever his current employers want him to.
- In The Witchlands, Mathew owns a chain of cafés, which are popular not because they serve good coffee (they don't), but because they're a front for a network of spies and one can buy more than just a vaguely coffee-like fluid there.
- Michael Coldsmith-Briggs III, Code Name "Archangel" in Airwolf. It is stated in the fluff that he is able to "move the Sixth Fleet". Which is a mistake, because that happens to be whatever is in the Mediterranean at the time, not a specific carrier group.
- Alias had a villainous example in Arvin Sloane, and heroic examples in Jack Bristow and Marcus Dixon.
- Babylon 5:
- It's easy to forget that whoever happened to be in charge of the Rangers at any particular time had this as their primary mission, until the Shadow War broke out and the Rangers were remade into a Badass Army.
- To a lesser extent, Commander Ivanova sometimes filled this role, gathering information from different sources for Captain Sheridan, in line with her role as the station's Executive Officer. In fact, it's a bit of a running theme that it's very difficult for anyone to do anything over a long period of time without her finding out about it somehow, even when it's ostensibly a secret they'd rather keep from her.
- And in the last season, Michael Garibaldi, then later Tessa Holloran filled this role for the Interstellar Alliance.
- G'Kar also did this for the Narn Resistance. Needless to say, with Babylon 5 pretty much being a City of Spies, you run into a lot of characters being The Spymaster for various governments and organizations over the years.
- The Ancient in Beastmaster knows all there was, is and will be (he makes reference to humanity's future). He teaches this in a lesser extent to his sorcerers, who he gives a magic crystal ball to see anything they please, item which apparently he doesn't need to see himself.
- "Management" from Burn Notice (probably- we still don't know all that much about them...)
- Anson Fullerton along with Management. It helps to be the one all agents confide in.
- Colonel Hunter from Callan.
- Chuck has General Beckman.
- "Control", Robert McCall's former boss in The Equalizer.
- The Chief in Get Smart.
- Mary Spalding on Intelligence (2006).
- Mycroft Holmes in Sherlock. In "A Scandal in Belgravia" he hires Sherlock to take care of an delicate case regarding the Royal Family, Sherlock snarks "So why don't you have one of your men take care of it?" Mycraft casually points out that they are all untrustworthy since "They all spy on people for money."
- Clayton Webb on JAG was this. He was also a chessmaster.
- Mr Waverly in The Man From UNCLE and The Girl from U.N.C.L.E..
- In The Sandbaggers, Neil Burnside is a rare example where the spymaster is the protagonist. Of course the focus of the show was on the strategic side of espionage, so it fits.
- Harry Pearce in Spooks.
- Star Trek: Deep Space Nine: Enabran Tain, the only head of the Obsidian Order to ever survive long enough to retire. When the Dominion decided to crush the Obsidian Order and Tal Shiar as a prelude to invading the Alpha Quadrant, they lured him out of retirement to destroy him as well: even in retirement he was simply too dangerous and powerful to ignore.
- The Game (2014) has 'Daddy'.
Religion and Myth
- Satan: As presented he acts so much like a typical spymaster that sometimes one wonders if some Ancient Spymaster did a Deal with the Devil.
- Zhuge Liang in Romance of the Three Kingdoms.
- Odin, god of trickery, deception and cunning, compensated for his sacrificed eye by sending his ravens Huginn ("thought") and Muninn ("memory") into the world to spy for him.
- Forgotten Realms has a lot of Cloak & Dagger stuff. The most interesting case is Inselm Hhune, a member of Knights of the Shield inner circle. For supporting Tethyr's new queen he was given a duchy not requiring much ruling and the post of spymaster. The fun part is that Lord Hhune quietly hates his king (he planned to marry the queen himself), but knows that Haedrak works with Harpers opposing his semi-secret society and got more than enough damning information on him. Since he has no clear idea how much the king is aware of his personal spy network, Lord Hhune just to be on the safe side surrenders more information that he'd like to, which in turn raises the risk of infiltration.
- In Star Frontiers, the Sathar are more likely to operate in this manner than directly against player characters. They recruit willing agents and sometimes brainwash others to act as saboteurs and informants. They are known for their ability to hypnotize people into seeing things from their point of view. Therefore, an unsuspecting person may act normal until it is time for him to carry out his function. The backstory explains that the Sathar realized that they could not defeat the United Planetary Federation in space combat, and thus chose a more indirect way to fight them.
- On the Rogue Trader roleplaying game, the Seneschal player class is half this, half Battle Butler, with the Flavor Text describing him as the man that creates vast intelligence networks on every port for his Intrepid Merchant master, as well as managing the day-to-day nuances of an interstellar trading empire (which in Warhammer 40,000 fashion includes the assassination of enemies of his master or even the deployment of armies).
- In The Elder Scrolls series, basically any leader of the Blades, an Ancient Order of Protectors that has long served the emperors of Tamriel as bodyguards and spies, has qualified throughout history. This was actually the title of the highest ranking Blade in each of the provinces during the height of the Third Empire. In Morrowind, "Spymaster" is literally the title of the rank of Caius Cosades, Morrowind's highest ranking Blade. His cover identity is ironically that of a stoner and he acts as the primary Quest Giver for the first half of the main quest.
- The announcer in Team Fortress 2 is this to her respective team, and possibly the instigator of the battle since her voice sounds the same for both sides (which isn't out of place in the game).
- It has been recently confirmed that the announcer is indeed controlling both sides of the war, and goes so far as to cause a war-like battle between two enemies who became friends, simply to keep that fact a secret.
- Guild Wars' Nightfall campaign introduces the Order of Whispers, a secret organization tasked to watch against evil, and the return of a certain forgotten god in particular. Their Crazy-Prepared leader is known only as The Master of Whispers. Lucky for you, he's also a Badass Grandpa - he joins your team once the time comes to stop spying and start kicking ass.
- In World of Warcraft we have Mathias Shaw, leader of both SI:7, the Kingdom of Stormwind's intelligence agency, and the more secretive and morally grey Stormwind Assassins.
- Fallout: New Vegas has Vulpes Inculta as the leader of the Frumentarii, who doesn't exactly conform to the trope as he's often afield and being directly involved in the actions he commands.
- As of version 1.2, the Van Graffs are heavily implied to have shades of this, as if you complete Cass' quest the "good" way, they somehow realize you were the one who exposed their plots to the NCR and become permanently hostile.
- Radiant Historia has Heiss, head of Specint, which deals in espionage and other sneaky business. Specint's existence is not a secret, and interestingly there is some tension between them and the army.
- Dragon Age:
- Varric Tethras is referred as "Dwarven Spymaster" in Dragon Age II, though it can be a borderline Informed Ability since you don't actually see him do any spying or intelligence-gathering. In fact, he has a veritable spy network spanning Kirkwall to gather intelligence first for the Dwarven Merchant Guild and his merchant brother, then for Hawke. You do get a few hints, mostly just those few people that were just leaving as you came in to talk to him.
- In Dragon Age: Inquisition, the Warden's former companion Leliana takes over this job for the title organization, having worked in more-or-less that same capacity for the Divine in the prior decade. Varric also joins the Inquisition but freely admits that Leliana is a better spymaster than him and sticks to the field agent (read: party member) duties.
- In the later parts of the first Neverwinter Nights, a female Player Character can strike up a romance with Lord Nasher's spymaster, who is given a surprisingly complete backstory but nevertheless has approximately zero actual influence on the plot.
- Yancy Westridge and Albatross in Alpha Protocol (the former runs the eponymous Government Conspiracy, the latter runs The Conspiracy).
- In Crusader Kings there are five council positions: Chancellor, Marshal, Steward, Lord Spiritual and Spymaster. Having a better spymaster than your enemies is crucial to discover plots and execute your own. Oh, and you better make sure he stays loyal to you, or else...
- Produce enough Spies in a Total War campaign and your faction leader might pick up a Spymaster as part of his Standard Royal Court. Though this does provide a global bonus to your espionage efforts, such tactics will increase your leader's Dread rating.
- Hiram Burrows in Dishonored was the former Spymaster of Dunwall before he staged the assassination of the queen and took over as the new ruler.
- Star Wars: The Old Republic has Keeper, who serves as the head of Imperial Intelligence and the boss of the Imperial Agent. A large part of his job is to make sure that an Empire built on the foundations of habitual betrayal and psychotic supervillainy doesn't completely fall apart. Compared to most other Imperial figures in the game, he's largely an Anti-Villain who avoids the dog-kicking evil prevalent among other Imperial/Sith figures and is usually a Reasonable Authority Figure to the Agent.
- Deande from Battleborn is the Spymistress of the Jennerit Imperium and right hand of Lothar Rendain. In secret though, she's been helping Jennerit rebels who disagree with Rendain's regime, and sabotaging Rendain's plans right underneath the Lord Commander's nose.
- Ravenmark: Scourge of Estellion: Benjamin Allsworth is a nondescript, perpetually smiling dwarf who serves as the Sotran Trade Ambassador to The Empire. He also happens to be in charge of the Commonwealth's intelligence network. He frequently has dealings with his childhood friend and occasional rival Crumston Caldare, his halfling counterpart in the Empire. Both have "Spymaster" titles in their respective governments.
- Mr Socrates from Butch Cassidy and the Sundance Kids.
- Number One from Cool McCool.
- J. Gander Hooter from Darkwing Duck.
- Transformers has Soundwave, Decepticon Communications Officer and the master of a loyal cadre of spy cassette minions.
- Star Wars Rebels gives us Agent Kallus of the Imperial Security Beureau. Played with, however, in that he isn't the leader of the ISB, but he's the only one seen on the series and is responsible for overseeing most Imperial spies throughout the show's first season.
- This page might as well have the picture of Markus Wolf of STASI/HVA on top of it.
- Stewart Menzies of the British Secret Service was like the classic Spymaster of fiction too. Somehow the profession just seems to breed people like that.
- Captain Sir George Mansfield Smith-Cumming, the first head of the Secret Intelligence Service, whose particular party trick involved stabbing his false leg with a penknife. To this day heads of SIS are called "C".
- Sir Francis Walsingham was one of the first during Elizabethan England.
- "Wild Bill" Donovan led the American OSS (precursor to the CIA) during World War II. As his nickname suggests, he was anything but cold, dour, or reserved — essentially he was the Boisterous Bruiser running a spy agency.
- Alan Dulles, a somewhat stiff Boston Brahmin was Chief of Station for the OSS in Switzerland and later boss of the CIA. One of his curious tactics during World War II was to make it as obvious who he was as he could and then wait for recruits to show up. Interestingly that worked quite well and he got one or two very useful moles.
- In the USSR, being head of the KGB made you pretty powerful. Beriya made a power-grab after Stalin's death and lost, being executed. Yuri Andropov won, spending two years as General Secretary before dying.
- J. Edgar Hoover.
- Benjamin Franklin. When he returned from France after The American Revolution Congress did an audit of his expenses. When asked about some money that was missing Franklin replied effectively that they didn't want to know. Likely at least some of that was money he had spent on intrigue and strange doings.
- Chances are that at least some of that money went to him financing his pirate fleet. Yes, Ben Franklin hired out pirates on the British, you can't make that up. Sadly, it... didn't work out for a number of reasons.
- On that same note, George Washington skirts this trope. He was known for actively deploying spies during The American Revolution to bring him back information about the British on top of his role as Four-Star Badass. However, it got to the point that juggling both these responsibilities became a bit overwhelming, and wrote back to a spy who sent him a report apologizing for forgetting who he was and what he was doing, and could he please reiterate his mission. Of course, the majority of Washington's spymastering was delegated to Benjamin Tallmadge, head of the Culper Ring. Among other things, they may have been the guys who worked out Benedict Arnold's betrayal.
- In the 19th century, the Duke of Caxias acquired some fame for pioneering modern counter-insurgency tactics of espionage against his opponents to devastating effect, spreading chaos and betrayal amongst those who opposed him.
- Isser Harel, the second director of Mossad (full translated title: Institute for Intelligence and Special Operations) and the Shin Bet (usually translated as the Israel Security Agency), was one of these. He was also quite nebbish and his personal life was dominated by his wife. The story goes that his neighbors thought he was a mid-level bank employee, rather than one of the most powerful men in Israel.
- In World War II, Winston Churchill had William Stephenson as his spymaster, better known by his Code Name, Intrepid.
- Not content with being the only one among Napoleon's marshals who was never defeated, Louis-Nicolas Davout also had a very impressive network of military intelligence, which of course increased the tension between him and his fellow commanders. Joseph Fouché, Napoleon's most famous Minister of Police, was also known as the best-informed man in France and is commonly depicted as such in fiction (usually to the expense of his successor, General Savary, who is generally shown as being sinister but incompetent or just plain dimwitted).
- Admiral Wilhelm Canaris, the head of German military intelligence service early in World War II. Unique in that he both spied for and against his own government at the same time, being both a staunch German patriot and a determined enemy of Nazis. Given the circumstances, details of his wartime activities are difficult to piece together accurately.