Fools Guild

A series of historical murder mystery novels by Alan Gordon, set at the time that the The High Middle Ages was starting to tail off, detailing the adventures of Theophilos, a jester belonging to the titular Guild, an organisation that is basically You Meddling Kids taken to Machiavellian extremes.

The Guild's self-imposed remit (executed either via subtle manipulation or just bumping the right people off at the right time) is to prevent wars, or failing that, to end them as quickly as possible, all while keeping the whole thing secret and trying not to piss off a Corrupt Church that seems to be losing its patience with them.

One of the series' more beguiling ideas is that Theophilos was Feste, the Clown from Shakespeare's Twelfth Night. He's also hinted to be the Fool in King Lear. The first book in the series is a sequel to Twelfth Night, which sees Theophilos going back to Illyria incognito to solve the murder of the Duke.

There are eight novels in total, though hopefully more will be forthcoming without readers having to resort to standing on the author's lawn with a box of cakes in one hand and a pitchfork in the other.

The series contains examples of:

 * Affectionate Nickname: Theophilos and Claudia occasionally refer to each other as  and 'Fool', though the extent to which either of them is a nickname could be debated, seeing as they're just plain descriptors as well. As far as Claudia is concerned, 'Apprentice' is most definitely not this. Claudia also mentions that she always thinks of Theo as 'Feste', sometimes when he's pissed her off, but mostly involving the fun variety of Say My Name situation.
 * The Alcoholic: Theo insists he isn't one. Everyone else seems to think otherwise. Though to be fair, the booze back then was a hell of a lot safer to drink that the water. Maybe he's just really thirsty?
 * Code Name: Taken Up to Eleven. Jesters have a Guild Name, a purely internal name which will never be used in the field. It's mainly used to identify them to other Guild members and for administrative purposes. In addition, they adopt secondary, professional codenames while engaged in fieldwork. And then there's the names they adopt for going undercover as non-Jesters. Theophilos alone has been known throughout the series as Feste, Octavius, Droignion, and Tan Pierre, but he says at one point he's had so many code names over the years, even he's forgotten some of them.
 * Crowning Moment of Heartwarming: So what if Helga's nearly thirteen; for the very first time in her life, she has a doll of her own.
 * Deadpan Snarker: All fools are this, by necessity if not inclination. Pretty much Truth in Television. Alan Gordon himself is revealled to be one in the appendix of The Lark's Lament, if the titles of an increasingly vitriolic exchange of essays with another historian are anything to go by.
 * Drinking On Duty: Terence in An Antic Disposition, after . He's stated to be so mashed that juggling as little as three clubs takes more effort than would need to be expended by the youngest of Guild trainees, and Terence is a full-fledged and long-serving Jester.
 * Drowning My Sorrows: Theophilos a few times, notably after witnessing the massacre of captives at Acre in The Widow of Jerusalem (doubles as I Need a Freaking Drink). Possibly spent the fifteen years between Twelfth Night and Thirteenth Night.
 * Five-Man Band: The Fools in Byzantium are this.
 * The Hero: Theophilos/Feste.
 * The Lancer: Claudia/Aglaia.
 * The Smart Guy: Rico.
 * The Big Guy: Plossus 'the Colossus'. Okay, it's because he's a stiltwalker, but still...
 * The Sixth Ranger: Xintziphitzes.
 * Good Parents: Theo and Claudia are most definitely this. To baby Portia, and their apparently Happily Adopted Apprentice Helga, anyway. Claudia.
 * The Jester: Indeed.
 * Jesus Was Way Cool: Most Fools, and Theo especially, have no time for the church and the clergy. But they seem to genuinely love and revere Jesus, who they refer to as 'The First Fool'. If you want to stay on his good side, do not make fun of Jesus in front of Theo.
 * Knife Nut: Theophilos. In The Lark's Lament, what was supposed to be a routine visit to convince an abbey-dwelling ex-Guildmember to assume the bishopric of Toulouse has suddenly turned into an incredibly complex murder investigation, but Theo's more pissed off at having to leave his favourite knife back at the abbey..
 * Literary Agent Hypothesis: The first half of the series was apparently based on papers discovered in an abbey in Ireland; the second half is based on more papers uncovered after an earthquake in an Italian village. Also implied to be the case for some of Shakespeare's plays.
 * Magnificent Bastard: Par for the course for a successful Guild operative, but Theo is this with bells on.
 * Mythology Gag: In Thirteenth Night, Theo is trying to work out which of Orsino's townsfolk could be the returned and revenge-seeking Malvolio. Still, at least Theo's disguised as a German spice merchant, so if Malvolio is in town, he has no idea that 'Feste' is there to look for him. When Theo arrives back at his room at The Elephant, he finds a pair of yellow cross-gartered stockings on the bed. He checks out immediately.
 * Similarly, Theo and Claudia's child, Portia is born on the sixth of January.
 * Only Known By Their Nickname: Happens to Terrence, in An Antic Disposition. After introducing himself as "Terrence of York" to the infant Amleth, the kid latches on to the wrong end of the sentence and refuses to call Terrence anything but "Yorick". Eventually, everyone ends up calling him Yorick.
 * Playing Drunk: One of Theo's specialities, used to eavesdrop, misdirect, or to illict In Vino Veritas from the person he's pulling it on.
 * Plot Hole: At the end of An Antic Disposition, Claudia speculates that Theophilos is . He isn't, he's  . And considering he says in Jester Leaps In that he had to tell Claudia his real name when they got married, she should really know that...
 * Retired Badass: Father Gerald. Retired from fieldwork, anyway. He's still pulling the strings of a spy network that spans Europe and parts of the Holy Land despite being in his seventies and stone blind.
 * Single Woman Seeks Good Man: More, but this is the main reason Claudia married Theophilos.
 * Shout Out to Shakespeare: Reasonably safe to assume that there will be many.
 * Shown Their Work: Alan Gordon is a Grand Master of this. His descriptions of life in 13th century Europe, especially Byzantium, are staggeringly detailed and evocative. Ungodly impressive when you find out he's not a professional historian. Guy's a lawyer, and is heavily involved with the Legal Aid Society. Speculation abounds as to whether he sleeps, ever. Also came up with a damn fine hypothesis as to how the life stories of Theophilos the Jester could have found their way into the hands of one William Shakespeare. If he comes across even a fleeting mention of specific jesters in any of the sources of the setting and time period he's currently working on, you can damn well expect characters either named after them or representing them to make an appearance. The sheer amount of Historical Domain Characters in general must number in the hundreds; One book, The Widow of Jerusalem, seems to contain something like half the characters of Kingdom of Heaven (albeit slightly more historically accurate versions). And that's before he starts adding Shakespeare's characters...
 * Stock Unsolved Mysteries: A rather obscure one is apparently 'solved' by Theophilos' account of the Fourth Crusade's siege of Byzantium, concerning a Venetian banner of St. Mark that was unaccountably, yet briefly, raised on one of the city's towers. This series is like porn for Medieval historians.
 * Take That: Possibly a very, very minor one against Shakespeare, in the case of Sebastian and Olivia. Yeah, turns out marrying someone on the basis that they actually fell in love with your transvestite sister doesn't make for a stable marriage. Alan Gordon swaps these with his academic rival in the Lark's Lament appendix essay-duel.
 * Tear Jerker: An extremely poignant one comes literally out of nowhere in The Lark's Lament. The Fool Family passes a herb seller, and Theo remarks quietly to Claudia that whenever he smells herbs, he imagines being a small boy being held by his mother..
 * Ugly Guy, Hot Wife: Okay, so Theophilos is by no means ugly, but he's usually described as being a bit on the tall and gangly side. I think he mentions having a slightly larger than average nose at some point. Claudia on the other hand is attractive, a kickass fighter, a crack shot with a bow, something of a Fool Prodigy and was  to marry Theo. Helga the Apprentice muses on the fact that the female novices don't understand exactly what Claudia sees in Theo, but concludes that since Claudia loves him, and he has the complete trust of Father Gerald, the guy really must be something special.
 * Very Loosely Based on a True Story: Quite a few of Shakespeare's plays are this, if the Literary Agent Hypothesis is to be believed.
 * What Happened to The Mouse?: Happens in-universe, in Thirteenth Night; apparently, Viola's always found an alleged shipwreck that leaves no actual wreckage, and the survivors' luggage miraculously intact, to be more than a little bit suspect.
 * Whole Episode Flashback: After tantalising hints in the first three books, two of these turn up at once. Book four, The Widow of Jerusalem, details one of Theo's past assignments in the Holy Land, and book five, An Antic Disposition, is kind of his Origins Episode.
 * Wholesome Crossdresser: Claudia was one for years, and is one for most of the first and second books. Though in Thirteenth Night, she seems to hint that.
 * Ye Olde Butcherede Englishe: The appendix to the first book says that some people will probably dismiss it for not being written in this, despite the original manuscripts being written in Medieval Tuscan. Translation Convention is firmly stated to be in play.