Literature: Grandmaster of Theft

“The reality I’ve found is that sometimes doing what’s conventionally considered good – being nice, adhering to the laws, showing mercy, telling the truth – is not enough to ensure that the right things occur. I wish they were, truly I do, but I rather not deceive myself. Sometimes the only options people are left with are to either yield to their tormentors and be a victim or to do what’s conventionally considered ‘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.
  • 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.
  • The Con: See The Caper.
  • 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
  • Experienced Protagonist: Cassidy & Wynn are already established vigilante thieves who have run successful capers and knowledgeable about the criminal underworld when the story starts.
  • 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 swapped the real one for a fake.
  • Gadget Watch: Cassidy owns one that doubles as a grappling hook watch.
  • 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 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.
  • Hero Secret Service: The Grandmaster Gang are this to Cass, serving as her support and assistants so she can survive in the criminal underworld.
  • Hired to Hunt Yourself: The Grandmaster Gang joins Narcissa's operation against The Grandmaster.
  • I Surrender, Suckers: Cassidy uses this to escape capture from Gale during the train heist.
  • Just Like Robin Hood: See We Help the Helpless
  • 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.
  • 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.
  • 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.
  • 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.
  • 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, who sell their security services to the highest bidders.
  • 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.
  • 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.
  • Their First Time: Cassidy & Rebecca sleep with one another for the 1st time, as documented in the side story Behind Closed Doors.
  • 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.
  • 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.

Alternative Title(s):

Grandmaster Of Theft