->'''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.
-->-- ''Webcomic/GirlGenius''

TheHandler of handlers, moving spies about all over the world. Often TheChessmaster. 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 KnowledgeBroker for when the Spymaster is operating freelance.



[[folder: AnimeAndManga]]
* In ''Manga/ShoukokuNoAltair'', 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.

* ''Comicbook/TheLeagueOfExtraordinaryGentlemen'' features Mycroft Holmes (Franchise/SherlockHolmes' brother), then later Harry Lime from ''Film/TheThirdMan'' 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 Franchise/TheDCU.
* ''ComicBook/NickFury'': Director of S.H.I.E.L.D. takes a [[RefugeInAudacity very]] [[BoisterousBruiser hands-on approach]] to this job. He's pretty much the MemeticBadass of the Marvel Universe
** Pete Wisdom, while not the head of his agency, serves as the closest thing to a counter-part Nick Fury has in MI-13, Britain's paranormal agency.
** Recently, [[ComicBookCaptainAmerica Steve Rogers]] served his country in this manner upon returning to life, operating as a Nick Fury-esque spy.
* Recurring ''ComicBook/IronMan'' 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 ''ComicBook/StarWarsLegacy''.
* Paul Crocker, Director of Operations, from ''ComicBook/QueenAndCountry''. Very much a SpiritualSuccessor to [[TheSandbaggers Neil Burnside]].
* The ComicBook/RedSkull more or less had this job when he was with ThoseWackyNazis.

* Arthur from ''Film/KingsmanTheSecretService''. He's the movie's answer to [[Franchise/JamesBond M]]. As the head of the agency, every Knight answers to him.

[[folder:Fan Works]]
* ''Fanfic/WhatAboutWitchQueen'' 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 ''FanFic/BadFutureCrusaders'', Featherweight serves as this to [[BigBad Queen]] [[FallenHero 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 ComicBook/NickFury, ''Fanfic/ChildOfTheStorm'' also has Peter Wisdom (Fury's protege and counterpart at [=MI13=]), Lucius Malfoy (who served this role for Voldemort), and Loki (who felt, as part of his [[TheAtoner reformation]], that this was the best way to serve Thor and Asgard).

* Varys "the Spider" in ''Literature/ASongOfIceAndFire'' is the Master of Spies and likes saying he gets his information from his "little birds".
* "Control" in the George Smiley books by Creator/JohnLeCarre 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 [[SecretIntelligenceService SIS]], also the basis for "M".
* Javelin from ''Literature/TheBelgariad'' 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 TheChessmaster, 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. [[spoiler: 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 ''Literature/MattHelm'' novels. "Mac" (Helm's boss).
* [[http://tinyurl.com/6qe5yq "M" (Sir Miles Messervy, later Admiral Hargreaves, then Barbara Mawsley)]] of [=MI6=] in the ''Franchise/JamesBond'' novels and movies.
* In Creator/LoisMcMasterBujold's Literature/VorkosiganSaga, Simon Illyan is the head of [=ImpSec=] the spying and counterspying organisation of Barrayar. He also plays the role of DaChief to Miles.
** Illyan's predecessor, the legendary Captain Negri, was this in spades.
* Rufus of the ''Literature/BlackfordOakes'' series by William Buckley.
* Dr. Harold Smith from the ''Literature/{{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 Sigizmund Dijkstra is the Spymaster of Kingdom of Redania and one of the principal players in Andrzej Sapkowski's ''Literature/TheWitcher'' 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 [[spoiler:the fence Thraller is actually head of intelligence and the secret police.]]
* ''Literature/TortallUniverse'':
** 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 ''Literature/DaughterOfTheLioness'' books when she works for the raka in the Copper Isles. She eventually becomes the rebels' spymaster, takes down the Rittevons' own spymaster, and [[spoiler:becomes the spymaster for the country when the revolution succeeds]].
* ''Literature/SixteenThirtyTwo'' 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 [[Literature/TheSpellmongerSeries Spellmonger Series]]. She maintains a sinister alter ego known as "The Mother", the head of the castali intelligence apparatus known as "the Family".
** [[TheSpock Father Mutio Vitelleschi]], Superior General of the Society of Jesus, pretty much serves this function for Pope Urban VIII.
* "The Spider," a.k.a. [[spoiler: Dona Angiavesta Vorchenza]], in ''[[Literature/GentlemanBastard 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 [[spoiler: because she's a seemingly harmless old widow]].
** At the end of the book, the position is handed off to [[spoiler: ''two'' people, Don and Dona Salvara.]]
* Thufir Hawat in ''Literature/{{Dune}}''. One of the few intrigue tales that shows TheSpymaster's perspective.
* Salthar in the ''Literature/{{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 ''Literature/TheWheelOfTime'', where Pedron Niall's well-known spymaster, Omerna, is an incompetent decoy, and all the spying is actually done by his secretary.
** [[DirtyCoward Moghedien]] plays this role for [[QuirkyMinibossSquad 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, [[TheDragon Moridin]].
* Each of Creator/JamesHSchmitz's milieus has a spymaster:
** For ''Agent of Vega'', the Third Coordinator of the Vegan Confederacy.
** In ''Literature/TheWitchesOfKarres'', there's Sedmon of the Six Lives.
** In the ''Literature/FederationOfTheHub'', [[ColonelBadass Senior Commissioner]] Holati Tate, and (eventually revealed to be the grandmaster of them all) [[ReallySevenHundredYearsOld Pilch]].
* 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 ''Literature/BelisariusSeries''.
** 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.
* Reliable sources within ''Literature/TheDresdenFiles'' identify ArchangelUriel as {{God}}'s personal spymaster and "black ops guy".
** [[MagnificentBastard Nicodemus Archleone]] is the bearer of Uriel's opposite number, [[FallenAngel Anduriel]], who has the title "Master of Shadows."
* Imperial Inquisitor Meng Ki in the ''Literature/JudgeDee'' novel ''The Chinese Lake Murders".
* Angleton from ''Literature/TheLaundrySeries''. Notably, it's not his real name; Bob notes that only he could have gotten away with using [[http://en.wikipedia.org/wiki/James_Jesus_Angleton James Jesus Angleton]] as a ''MomDeGuerre''.
* In ''Marque And Reprisal'', the second book of the ''Literature/VattasWar'' series, it is revealed that [[spoiler: 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 [[spoiler: [[ExactlyWhatItSaysOnTheTin The Family Spy.]]]]
* The BigBad of the first four books of the ''Literature/XWingSeries'' is Ysanne Isard, Director of Imperial Intelligence, the de facto head of the Empire. Her fearsome skill at breaking captives down into {{Manchurian Agent}}s, and the ruthlessness shown when she [[KlingonPromotion 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 ''[[BattleTechExpandedUniverse 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 Franchise/TolkiensLegendarium, 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 MasterOfDisguise. 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 ''Literature/TheHobbit''. As a spymaster, Radagast would understandably be very low key and indirect by necessity.
* Louis Goliath of ''Literature/DoctrineOfLabyrinths''. Although he's perfectly willing to use hideous methods, from physical mutilation to MindRape, 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 ''Literature/SomewhereBeneathThoseWaves''. He's a particularly nasty example, since he [[spoiler: deliberately sets up one of his own spies in order to discredit an honest investigator]].
* Earth's spymaster in Creator/IsaacAsimov'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 [[spoiler: 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 [[EarthThatUsedToBeBetter looks down on Earth]] and so tend to have something of a blind spot when it comes to Earth's advantages.
* Bob Ritter from Creator/TomClancy's Literature/JackRyan 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 ''Literature/{{Safehold}}'' series, nearly every member of royalty we meet as TheGoodChancellor 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 ''[[Literature/HeraldsOfValdemar 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 ''Literature/ASymphonyOfEternity'' 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 LightningBruiser, 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 ''Literature/TheZombieKnight'', Ivan "[[RedBaron 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 [[PersonOfMassDestruction fearsome combatant]] in his own right, [[AsskickingEqualsAuthority as is anyone in the Abolish or Vanguard inner circles]].

[[folder:Live-Action TV]]
* Michael Coldsmith-Briggs III, CodeName "Archangel" in ''Series/{{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.
* ''Series/{{Alias}}'' had a villainous example in Arvin Sloane, and heroic examples in Jack Bristow and Marcus Dixon.
* ''Series/BabylonFive'':
** 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 BadassArmy.
** 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 [[TheLancer 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, [[spoiler: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 CityOfSpies, you run into a lot of characters being TheSpymaster for various governments and organizations over the years.
* The Ancient in ''Series/{{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 ''Series/BurnNotice'' (probably- we still don't know all ''that'' much about them...)
** [[spoiler:Anson Fullerton]] along with Management. It helps to be the one all agents confide in.
* Colonel Hunter from ''Series/{{Callan}}''.
* ''Series/{{Chuck}}'' has General Beckman.
* "Control", Robert [=McCall=]'s former boss in ''Series/TheEqualizer''.
* The Chief in ''Series/GetSmart''.
* Mary Spalding on ''Series/{{Intelligence 2006}}''.
* Mycroft Holmes in ''Series/{{Sherlock}}''. In "[[Recap/SherlockS02E01AScandalInBelgravia 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 [[GenreSavvy "They all spy on people for money."]]
* Clayton Webb on ''Series/{{JAG}}'' was this. He was also a chessmaster.
* Mr Waverly in ''Series/TheManFromUNCLE'' and ''Series/TheGirlFromUNCLE''.
* In ''Series/TheSandbaggers'', 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}}''.
* ''Series/StarTrekDeepSpaceNine'': Enabran Tain, the only head of the [[GovernmentAgencyOfFiction Obsidian Order]] to ever survive long enough to retire. When the Dominion decided to crush the Obsidian Order and [[GovernmentAgencyOfFiction 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.
* ''Series/TheGameUKTV'' has 'Daddy'.

[[folder:Religion and Myth]]
* {{Satan}}: As presented he acts so much like a typical spymaster that sometimes one wonders if some Ancient Spymaster did a DealWithTheDevil.
* Zhuge Liang in ''Literature/RomanceOfTheThreeKingdoms''.
* [[Myth/NorseMythology Odin]], god of trickery, deception and [[GuileHero cunning]], compensated for his [[ByTheEyesOfTheBlind sacrificed eye]] by sending his [[CleverCrows ravens]] Huginn ("thought") and Muninn ("memory") into the world to spy for him.

[[folder:Tabletop Games]]
* ''TabletopGame/ForgottenRealms'' has a lot of CloakAndDagger 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 ''TabletopGame/StarFrontiers'', 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 ''TabletopGame/RogueTrader'' roleplaying game, the Seneschal player class is half this, half BattleButler, with the FlavorText describing him as the man that creates vast intelligence networks on every port for his IntrepidMerchant master, as well as managing the day-to-day nuances of an interstellar trading empire (which in ''TabletopGame/{{Warhammer 40000}}'' fashion includes the assassination of enemies of his master or even the deployment of armies).

* Caius Cosades from ''VideoGame/TheElderScrollsIIIMorrowind'' is the local Blades (Tamriel's CIA) Spymaster. Normally, he poses as a stoner.
** Bonus points for "spymaster" literally being the name of his rank within the organization.
* The announcer in ''VideoGame/TeamFortress2'' 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.
* ''VideoGame/GuildWars''[='=] 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 CrazyPrepared leader is known only as [[NoNameGiven The Master of Whispers]]. Lucky for you, he's also a BadassGrandpa - he joins your team once the time comes to stop spying and start kicking ass.
* In ''VideoGame/WorldOfWarcraft'' 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.
* ''VideoGame/FalloutNewVegas'' 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, [[spoiler: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.]]
* ''VideoGame/RadiantHistoria'' 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.
* ''Franchise/DragonAge'':
** Varric Tethras is referred as "Dwarven Spymaster" in ''VideoGame/DragonAgeII'', though it can be a borderline InformedAbility 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 ''VideoGame/DragonAgeInquisition'', the [[VideoGame/DragonAgeOrigins Warden's]] [[TheFellowshipHasEnded former]] [[NonPlayerCompanion companion]] Leliana takes over this job for the title organization, having worked in more-or-less that same capacity for [[UsefulNotes/ThePope 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 ''VideoGame/NeverwinterNights'', a female PlayerCharacter 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 ''Videogame/AlphaProtocol'' (the former runs the eponymous GovernmentConspiracy, the latter runs TheConspiracy).
* In ''VideoGame/CrusaderKings'' there are five council positions: Chancellor, Marshal, Steward, Lord Spiritual and Spymaster. Having a better spymaster than your enemies is [[DeadlyDecadentCourt crucial to discover plots and execute your own]]. Oh, and you better make sure he ''stays'' loyal to you, or ''[[TheStarscream else...]]''
* Produce enough Spies in a ''VideoGame/TotalWar'' campaign and your faction leader might pick up a Spymaster as part of his StandardRoyalCourt. Though this does provide a global bonus to your espionage efforts, such tactics will increase your leader's [[KarmaMeter Dread rating]].
* Hiram Burrows in ''VideoGame/{{Dishonored}}'' was the former Spymaster of Dunwall before he staged the assassination of the queen and took over as the new ruler.
* ''Videogame/StarWarsTheOldRepublic'' 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 [[ChronicBackstabbingDisorder habitual betrayal]] and [[CardCarryingVillain psychotic supervillainy]] doesn't completely fall apart. Compared to most other Imperial figures in the game, he's largely an AntiVillain who avoids the dog-kicking evil prevalent among other Imperial/Sith figures and is usually a ReasonableAuthorityFigure to the Agent.

[[folder:Web Original]]
* Ayla from the ''Literature/WhateleyUniverse'' gives us the inside scoop on how a Spymaster is made. Mostly, Ayla uses [[TheCharmer Charisma]], [[TeenGenius Intelligence]], and [[ScrewTheRulesIHaveMoney Boatloads of Money]].

[[folder:Western Animation]]
* Mr Socrates from ''WesternAnimation/ButchCassidyAndTheSundanceKids''.
* Number One from ''WesternAnimation/CoolMcCool''.
* J. Gander Hooter from ''WesternAnimation/DarkwingDuck''.
* ''WesternAnimation/{{Transformers}}'' has Soundwave, Decepticon Communications Officer and the master of a loyal cadre of spy cassette minions.
* ''WesternAnimation/StarWarsRebels'' gives us Agent Kallus of the [[StateSec 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.

[[folder:Real Life]]
* This page might as well have the picture of [[http://en.wikipedia.org/wiki/Markus_Wolf 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 BoisterousBruiser 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 WorldWarII was to make it as [[RefugeInAudacity 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 [[TheMole 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.
* [[{{FBI}} J. Edgar Hoover]].
* Creator/BenjaminFranklin. When he returned from France after UsefulNotes/TheAmericanRevolution Congress did an audit of his expenses. When asked about some money that was missing Franklin replied effectively that they [[PlausibleDeniability 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. [[NotMakingThisUpDisclaimer 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, UsefulNotes/GeorgeWashington skirts this trope. He was known for actively deploying spies during UsefulNotes/TheAmericanRevolution to bring him back information about the British on top of his role as FourStarBadass. In a case of self-lampshading, 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.''
* In the 19th century, the UsefulNotes/DukeOfCaxias acquired some fame for pioneering modern [[http://en.wikipedia.org/wiki/Counter-insurgency 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 [[PlayingAgainstType was also]] quite [[JewishComplaining nebbish]] and his [[HenpeckedHusband 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 WorldWarTwo, WinstonChurchill had William Stephenson as his spymaster, better known by his CodeName, 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.