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.
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- 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... a crooked South African diamond magnate, an unscrupulous Australian land baron, and a brutal, brutish American prizefighter all fall into this category.
- 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' "f**" 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.