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Literature / Grandmaster of Theft

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“The reality I’ve found is that sometimes doing what’s conventionally considered good – being friendly, adhering to the laws, showing mercy, telling the truth – is not enough to ensure that the right things occur. Sometimes the only options people are left with are to either yield to their tormentors, to allow them to prosper in spite of why they’re prospering, or to do something ‘bad’ to set things right. It’s when predicaments such as these arise that we become a factor. We’re ‘the villains’ so people like you don’t have to be.”
Cassidy Cain

The Grandmaster of Theft series is a Criminal Procedural which follows the life & adventures of Cassidy Cain, the titular Lady Thief. Initially just a phantom thief who targeted white collar criminals, con artists, and the like to assist their victims or expose their transgression, one of Cass’ jobs finds her contending with a criminal mastermind far beyond her usual escapades. The end result of this conflict compels Cassidy to make them pay for what they've done.

To do so, she expands her own operations to form The Grandmaster Gang. She has the crew take on various jobs, partially to assist the various victims out there who cannot depend on the law and partially to strengthen and prepare her organization for Deus. Of course, cultivating a true team isn’t easy when there is pressure from both sides of the law, not to mention within the crew itself.


The first story, The Confessions of Cassidy Cain, can be read here.

This series wouldn't deserve to be called The Grandmaster of Theft if it didn't contain the following tropes:

  • Action Adventure Series
  • Arch-Enemy: Deus actively seeks to be this to Cassidy as a means of dealing with their boredom.
  • Asshole Victim: Narcissa Richmond, who is a jerkass Attention Whore who will do anything for publicity.
  • A Taste of Their Own Medicine: Cassidy is a firm believer in turnabout being fair play and she makes it a point to make her own actions as a criminal mirror those of her marks.
  • Battle of Wits: The series entire plot is based around these between The Grandmaster Gang & whoever the opposition at the time is.
  • The Bet: Cassidy ropes Narcissa into one regarding the events of the train challenge.
  • Bitch Alert: Narcissa's debut immediately makes clear where she stands.
  • Advertisement:
  • Black-Tie Infiltration: Cassidy's scheme during The Grandmaster's Gala Grift is to convince the mark to host a gala specifically so she can perform an infiltration.
  • The Caper: Jobs typically involve running a combination of heists & cons.
  • The Chessmaster: Cassidy, Deus, and Alana are all this, each of them progressively moving everybody and reacting to the other's schemes.
  • Clear My Name: Invoked by Cassidy as a pretext for why she wanted to work against The Grandmaster and assist Narcissa.
  • The Con: See The Caper.
  • Confess in Confidence: A priest example: Gerard Turner is a priest for The Followers of Yewel who Cassidy turns to for advice on how to proceed and to convince her not to kill Deus.
  • Covert Group: The Grandmaster Gang is this on account of everything they do being illegal.
  • Defeat Means Friendship: Invoked by Cassidy. She pretends to do this to infiltrate Narcissa's forces for The Con
  • The Everyman: Gerard Turner, who is extremely average in contrast to Cassidy and Wynn.
  • Experienced Protagonist: Cassidy & Wynn are already established vigilante thieves who have run successful capers and knowledgeable about the criminal underworld when the story starts.
  • Face Your Fears: Cassidy's counterphobic side leads her to continuing the job once Deus is involved and her desire not to be out of control again.
  • Fame Through Infamy: Narcissa's actions in the backstory are guided by this, with her belief that there is no such thing as bad publicity.
  • Family Business: Cain International
  • Fakin' MacGuffin: Brought up as a possibility about the copy of Adora's Tear they steal being a fake and later confirmed that Narcissa hide the real one and brought a fake.
  • Faked Kidnapping: How Cassidy comes up with a plan to trick her friend/love interest Rebecca into helping her scheme without her finding out.
  • Fake Weakness: Cassidy fakes being easily rattled by her schemes failure in front of Deus as a form of preloading for the future in case she ever needs to convince him that a defeat is real. She later exploits when trying to appear desperate when she's actually a step ahead.
  • Gambit Pileup: The Confessions of Cassidy Cain storyline progressively evolves into this. It starts as a straightforward caper, with Cassidy deciding to target Narcissa after Narcissa challenged her. Then Deus is revealed to be the mastermind of the challenge, Alana Arkland sends her chevalier Gale after Cassidy with a scheme to recruit her to work as her secret operate, Narcissa betrays the deal, and Cassidy is progressively playing Xanatos Speed Chess to turn everything around. All four sides are doing their best to play the circumstances to their advantage.
  • Genius Thriller
  • Good for Bad: The crew swaps Narcissa's replica of Adora's Tear with the real one.
  • Hero Secret Service: The Grandmaster Gang are this to Cass, serving as her support and assistants so she can survive in the criminal underworld.
  • Honor Before Reason: Gale's Fatal Flaw, according to Cass, is that he can be shamed into defeat.
  • Investigator Impersonation: See Clear My Name.
  • I Surrender, Suckers: Cassidy uses this to escape capture from Gale during the train heist.
  • Just Like Robin Hood: See We Help the Helpless
  • Kansas City Shuffle: Narcissa & Deus are led to believe with a fake con that The Grandmaster is desperate and her first open move against them with trying to turn Narcissa was her best try when in truth she had already completed the job.
  • King of Thieves: The Grandmaster of Theft title, which she made as a boast and impressive sounding title to threaten others with.
  • Lady and Knight: Cassidy & Wynn serve as a version of this, with Cass being a high society heiress & lady thief while Wynn is her bodyguard and enforcer.
  • Latex Perfection
  • Let No Crisis Go to Waste: Criminal mastermind trying to bait you? Use the fact they're even around as a bigger fish to distract the Sympathetic Inspector Antagonist from pursuing you.
  • Locked Out of the Fight: Inverted. Cassidy arranges this to happen on the train to lock out Narcissa's bodyguards so they can have a one on one.
  • MacGuffin: Adora's Tear serves as this for Confessions of Cassidy Cain. The crew's main objective is to steal this from Narcissa Richmond and return it to The Followers of Yewel while Narcissa is trying to keep it away from them.
  • The Mark: Due to her having direct access to Adora's Tear, Narcissa is this for Confessions.
  • The Man Behind the Man: Deus is this to Narcissa, creating the entire plan that she claimed credit for and being the one to actually move her as a piece.
  • Monumental Theft: The first heist of Confessions, by stealing the train itself.
  • Morality Kitchen Sink
  • Moving the Goalposts: Narcissa did this to The Followers in the backstory. She claimed she would sell Adora's Tear to them for half a million crowns and when they managed to gather that amount, she increased the price.
  • Must Let Them Get Away
  • Name of Cain: The Cain family as a whole, with Cassidy herself being the heir to their fortune and the heiress to Cain International.
  • Never Hurt an Innocent: One of Cassidy's rules on how the crew operates is that innocents can't be harmed in the course of their actions. Cass also uses this as the line that separates her from those she targets.
  • Obstacle Exposition
  • Pragmatic Hero: The mission statement of The Grandmaster Gang, with them being committed to doing the unpopular things for the common man.
  • Private Military Contractor: Sharpe Security is one, with it hiring out resources and bodyguards.
  • Redemption Rejection: Cassidy spends the earlier parts of Confessions trying to show mercy and reason with Narcissa to change as a person. Narcissa pretends to go along with it only long enough to get to safety then rejects her offer.
  • Refuge in Audacity: This is the reason why Cassidy doesn't cloak her true identity before the train heist occurs and why she openly runs a propositional con in front of a huge audience. She feels that by making a move that is so overt that others will conclude she can't actually be The Grandmaster of Theft because it's not the conventionally smartest move to make.
  • Secret Identity: The Grandmaster Gang keep their criminal side secret so as to avoid being arrested or being targeted by enemies.
  • Steal the Surroundings: The crew steals an entire train so Cass can have a face to face chat with Narcissa while she's on board.
  • Sympathetic Inspector Antagonist: Gale Crawford is a serious version of this. He pursues The Grandmaster Gang out of a sense of duty to the law.
  • Successful Sibling Syndrome: Brought up with Narcissa's backstory and as part of the reason she acts as she does to gain attention.
  • That's What I Would Do: Used all the time by Cassidy, who deduces her opponents all the time to figure out their most optimal moves and think around it.
  • Train Job: Narcissa challenges Cassidy to complete one of these early on in Confessions.
  • Traintop Battle: A very brief one between Cass and Gale. The terrain overall plays against her and so Cass avoids fighting as much as she can. Once she does, it's a short exchange.
  • The Unreveal: Since the Confession as narrated by Cassidy to someone, she makes it very clear she won't reveal what's inside her secret safe. It's implied to be something very intimate, but we don't get any detail.
  • We Help the Helpless: The stated reason for running cons and capers. Cass is primarily interested in supplying her power to those who lack and need it.
  • Xanatos Gambit: Cassidy's train heist plan. If they succeeded into frightening Narcissa into surrendering, she'd have been coerced into donating Adora's Tear to The Followers, ending the conflict. If Narcissa betrayed her and The Grandmaster Gang failed to retrieve Adora's Tear, the failure of the first plan triggered the start to the next plan because Narcissa is on guard and they can exploit that as an opening to get close.
  • Xanatos Speed Chess: While she is no slouch at figuring out things well in advance, Cassidy adapts on the fly to any new information or complications quickly and finds ways to adapt to or exploit any problems that come up.

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