- Captain Obvious Reveal: In the second book, Jean was just conning the mooks and isn't betraying Locke. Who really fell for that one? It doesn't help that there is zero evidence given throughout the book that Jean is growing dissatisfied enough to betray Locke.
- Complete Monster: The Falconer of Karthain became the leader of the magical supremacist wing of the Order of the Bondsmagi to spite his mother, and is the worst person that even that faction has to offer. A petty sadist who sees himself as part of a Superior Species, Falconer persuades the rest of the Bondsmagi to accept Capa Raza's black contract, then offers to carry out the contract himself, murdering seven of Capa Barsavi's garristas, his daughter Nazca, and finally Barsavi himself for Raza, and torturing Locke Lamora into assisting with Raza's plot. Following Barsavi's death, Falconer murders Locke's friends Calo and Galdo, and his apprentice, Bug, and hypnotizes Dona Vorchenza into allowing statues full of Wraithstone to placed at Duke Nicovante's ball, all as part of Capa Raza's plot to "gentle" the nobility of Camorr. Captured and crippled by Locke and Jean after his final attempt at murdering them goes awry, Falconer survives, and makes a comeback, murdering the nurse-attendant who had kept him alive, and then having his mother, Archedama Patience, eaten alive by crows.
- Cry for the Devil: Prior to the final duel in Lies, readers are treated to a section from the perspective of the Gray King. While it in no way excuses his actions, his lifelong trauma is made very clear - and with his scheme failing utterly and his family and crew all dead, he's essentially lost every reason he ever had to live. Twice.
- Does This Remind You of Anything?: Karthain is ostensibly a democracy with a two-party system, but the parties are interchangeable and always serve at the pleasure of a small group of elites. It's a common criticism in Scott Lynch's native United States that the political theater of elections is just to provide the illusion of choice, and that all politicians will ultimately serve special interests who finance their campaigns and keep them in office.
- Genius Bonus: Camorr was no doubt named for the Camorra, a Neapolitan crime syndicate with a more horizontal hierarchy than its Sicilian Mafia rival. Like Camorra clans, Camorr gangs are independent of one another, aside from being under Barsavi.
- Magnificent Bastard: Luciano Anatolius, alias the Grey King, alias Capa Raza, used Locke Lamora and the other Gentleman Bastards as disposable pawns in his campaign against Capa Barsavi and the Camorri nobility, forcing Locke to impersonate him so that he might fake his own death, and then killing off most of the team with ease. With twenty-two years to plan out his revenge on Barsavi and the nobles for the death of his family, Anatolius leaves few details unattended to, killing off Barsavi's gang bosses and inserting his own men into leadership positions, hiding his Co-Dragons among Barsavi's personal bodyguard, and hypnotizing the chief of the Secret Police into bringing his hidden Wraithstone weapons into the Duke's ball. Successful at taking over the Barsavi organization and killing off Barsavi's entire family in the process, the newly minted Capa Raza comes within a hairsbreadth of taking out the whole of the Camorri nobility, before Locke and Jean manage to halt his rampage.
- Squick: Selendri's disfiguration and Requin's revenge. Also, the horse urine thing.
- Tear Jerker:
- The scene of Bug's death.
- Ezri's Heroic Sacrifice
- Unintentionally Sympathetic: Maxilan Stragos, one of the main antagonists of Red Seas Under Red Skies. The narrative treats him as truly detestable but he doesn't really do anything all that heinous on screen, has a number of redeeming qualities, and his actions are those of a Well-Intentioned Extremist trying to fight against the pirates plaguing his territory. For this reason the Fate Worse than Death that Locke and Jean give him at the end of the book, which is supposed to be karmic, can be seen as unnecessarily cruel. He's not even responsible for the death they're punishing him for. That was another, independent villain.
- On the other hand he's a pompous ass, an insufferably self-righteous blackmailer and poisoner, and it's heavily implied that he cares far more about keeping/hoarding power than the pirates, which aren't really a danger to Tal Verrar. Not to mention the entire plot happens b/c he wants a war to shore up his power base.
YMMV / Gentleman Bastard