The Spymaster

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.

Comic Books

 * 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
 * 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, Steve Rogers served his country in this manner upon returning to life, operating as a Nick Fury-esque spy.
 * 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.

Literature
""If Dijkstra says it's midday, but it's pitch dark on the street, start to worry about the sun's fate.""
 * Varys "the Spider" in A Song of Ice and Fire is the Master of Spies and likes saying he gets his information from his "little birds".
 * "Control" in the George Smiley books by John Le Carre and his Soviet counterpart "Karla". Arguably Smiley himself at times, especially in Smiley's People.
 * 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.
 * 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.
 * 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 Sigizmund Dijkstra is the Spymaster of Kingdom of Redania and one of the principal players in Andrzej Sapkowski's The Witcher series.


 * And in the game based on them
 * Sir Miles of Olau, George Cooper of Pirate's Swoop, and eventually Alianne Cooper (George's daughter and Miles's adopted granddaughter) are this in Tamora Pierce's Tortall series, particularly in the two Trickster novels.
 * The Trickster series also introduces a evil Spymaster in the form of Topabaw, the spymaster for the Copper Isles whose Shadow Man status has made him a terrifying figure in the isles and concealed the fact that he has grown lazy over the years and is much less dangerous than he used to be. He's eventually executed after failing multiple times to stop Alianne's schemes, Aly being new to the isles and therefore not so quick to buy the myth of his invincibility.
 * Spymaster Fransico Nasi from the 1632 novels. His job is Exactly What It Says On the Tin.
 * Father Mutio Vitelleschi, Superior General of the Society of Jesus, pretty much serves this function for Pope Urban VIII.
 * "The Spider," a.k.a., 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.
 * At the end of the book, the position is handed off to
 * Thufir Hawat in Dune. One of the few intrigue tales that shows The Spymaster's perspective.
 * 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.
 * Each of James H Schmitz's mileus has a spymaster:
 * For Agent of Vega, the Third Coordinator of the Vegan Confederacy.
 * In The Witches of Karres, there's Sedmon of the Six Lives.
 * In the Federation of the Hub, Senior Commissioner Holati Tate, and (eventually revealed to be the grandmaster of them all) 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 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.
 * Reliable sources within The Dresden Files identify Archangel Uriel as God's personal spymaster and "black ops guy".
 * Imperial Inquisitor Meng Ki in the Judge Dee novel ''The Chinese Lake Murders".
 * Angleton from The Laundry Series. Notably, it's not his real name; Bob notes that only he could have gotten away with using James Jesus Angleton as a nom de guerre.

Live Action TV

 * Clayton Webb on JAG was this. He was also a chessmaster.
 * The Chief in Get Smart.
 * Harry Pearce in Spooks.
 * 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.
 * Colonel Hunter from Callan.
 * "Control", Robert McCall's former boss in The Equalizer.
 * 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 case of Did Not Do the Research, because that happens to be whatever is in the Mediterranean at the time, not a specific carrier group.
 * "Management" from Burn Notice (probably- we still don't know all that much about them...)
 * Mr Waverly in The Man From UNCLE.
 * 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.
 * 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 was remade into a Badass Army.
 * To a lesser extent, Commander Ivonova sometimes filled this role, gathering information from different sources for Captain Sheridan, in line with her role as the station's Executive Officer.
 * And in the last season, 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.
 * Mary Spalding on Intelligence.
 * Alias had a villainous example in Arvin Sloane, and heroic examples in Jack Bristow and Marcus Dixon.
 * Chuck has General Beckman.

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.

Tabletop RPG

 * Forgotten Realms has a lot of Cloak and 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.

Video Games

 * Caius Cosades from The Elder Scrolls III: Morrowind 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 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,
 * 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.
 * 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 (which kinda means he is just that good). 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 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).

Web Original

 * Ayla from the Whateley Universe gives us the inside scoop on how a Spymaster is made. Mostly, Ayla uses Charisma, Intelligence, and Boatloads of Money.

Western Animation

 * Mr Socrates from Butch Cassidy and The Sundance Kids.
 * Number One from Cool McCool.
 * Transformers has Soundwave, Decepticon Communications Officer and the master of a loyal cadre of spy cassette minions.
 * J. Gander Hooter from Darkwing Duck.

Real Life

 * 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.
 * 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. 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.
 * 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 Two, Winston Churchill had William Stephenson as his spymaster, better known by his Code Name, Intrepid.