Raffles

Raffles is the Gentleman Thief protagonist of a series of stories by E.W. Hornung, Arthur Conan Doyle's brother-in-law. Intended as a sort of dark reflection of Sherlock Holmes, rather than an asocial Bunny Ears Lawyer who works toward law, Raffles is a seemingly respectable gentleman who commits crimes, and rather than the bluff Watson, he is assisted by his chronicler, "Bunny" Manders, something of a Cowardly Sidekick.

Contains examples of:

 * Affably Evil: Raffles is this trope---he's charming, funny, a good friend to have and a very valuable man to have on your side in a tight pinch...and an unrepentant thief.
 * Ambiguously Gay: Raffles and Bunny, who have lots of Ho Yay. Raffles is described as associating with Oscar Wilde's aesthetic movement and dressing according to that fashion, but being surprisingly macho.
 * Anti-Hero / Villain Protagonist: Raffles varies between the two
 * Black and Gray Morality: While Raffles is presented as Affably Evil, some of his victims are no saints, and could be said to deserve some comeuppance...
 * Even Evil Has Standards: Raffles will not steal from a home while he is a guest there (stealing from other guests is OK by him, though); he will not cheat at games; he will not betray a fellow thief, even one who's blackmailing him (he despises blackmailers); and in many ways, thieves or no, he and Bunny retain most of their late-Victorian upper-class code.
 * Evil Counterpart: As noted above, Raffles and Bunny are this to Holmes and Watson.
 * Gentleman Thief: One of the first, although Raffles steals because he needs the money- he couldn't keep up his front as a gentleman-of-leisure without the profits from his crimes.
 * Have a Gay Old Time: Although there would be plenty of Ho Yay without it, it's definitely furthered by Bunny's references to himself as being Raffles' "fag" while they were at school together. There is also some straight-faced talk of man-diddling.
 * Hero Antagonist: Inspector Mackenzie of Scotland Yard.
 * Important Haircut: Raffles used to have a mustache, but he shaved it off after his first heist.
 * Master of Disguise: Raffles, in a dept to Sherlock Holmes.
 * Of Course I Smoke: Mirabel Renny in "The Raffles Bombshell".
 * Pay Evil Unto Evil: Raffles often steals from nasty, new-money people. And although he does not normally kill, he does cause the deaths of some very nasty Camorra men through an inadvertent Plan. He also connives in allowing a murderer to escape, but the person in question killed a would-be blackmailer, which, by the standards of the time, "didn't count," according to Orwell's essay on Raffles.
 * Seme / Uke: Again, the pair aren't explicitly gay, but Raffles and Bunny fit rather well into these respective tropes.
 * Sensitive Guy and Manly Man: Bunny and Raffles.
 * Strangled By the Red String: "An Old Flame", also a Psycho Ex-Girlfriend
 * Unbuilt Trope: While Raffles isn't the first Gentleman Thief, he comes from an era where people weren't as accepting of criminal heroes (who got away with it), and so he reads like a nastier version of the Gentleman Thief we are familiar with (Arsène Lupin is the straighter version of that trope).
 * The Watson: Bunny, of course.