* AdaptationDisplacement: The movie is both better known and better liked than the 1978 novel which inspired it, due to its screenplay having more quotable dialogue and better plot twists for TheCaper.
* AnticlimaxBoss: Played intentionally as part of TheCon. [[spoiler:Palmer is barely able to stand after defeating his old nemesis in the final fight, only to learn that he must face ''another'' badass boxer, Minoso Torres. Unbeknownst to him, however, Torres and Caine have already arranged a fix, and Torres lays down after one punch.]]
* EnsembleDarkhorse:
** Hambone Busby only has about ten minutes of screen time, but he's probably the best-liked of the boxers Honey Roy fights due to his decent skills in the ring and his RootingForTheEmpire moment fighting in an effort to save his brother's life (who is facing being murdered for taking a dive during his fight).
** She may be a DesignatedLoveInterest who doesn't appear until about halfway through the movie, but Emily still brings a lot of charm to the movie for her sympathetic reasons for helping Caine and her AwesomeByAnalysis deduction of how he, Wolf, and Fitz are working together to con Gillon. It helps that a young Creator/HeatherGraham plays her.
* MagnificentBastard: [[LovableRogue Gabriel Caine]] is a cheeky con artist introduced helping other prisoners escape despite the scrutiny of the warden for a hefty sum. After being released, Caine deliberately gets into a rivalry with Gillon, and then, seemingly on a whim, decides to back up a drunken "stranger" who wagers Caine's friend, retired boxer "Honey" Roy Palmer, can beat ten local men in one day. Caine deliberately gets into debt with a loan shark so that Roy will feel obligated to come out of retirement and help him. Starting with a small bet, Caine repeatedly ups the ante to bankrupt Gillon, and takes great advantage of the ExactWords of the tournament's rules. While he suffers some genuine setbacks, Caine has been manipulating Gillon into selecting a SuperRinger who barely even qualifies as a legal resident of Diggstown, since long before the initial wager Just when Gillon thinks he's won, Caine [[spoiler:signals for the ringer to take a dive]], [[IronicEcho deliberately mimicking how Gillon did so earlier.]] [[EveryoneHasStandards Caine shows a deal of shock and sympathy for Gillon's various victims]], is friendly to his allies, and is prepared to throw in the towel if Palmer can't take any more punishment in the ring.
%%* SugarWiki/MomentOfAwesome: Caine's final con against Gillion.
* MoralEventHorizon: Boss Gillon is corrupt, but his intelligence, cordial demeanor, good relationship with his son, and treating Honey Roy as a WorthyOpponent initially make him seem AffablyEvil at worst. Then it turns out that [[spoiler:he drugged his own fighter, hometown hero Charles Macon Diggs, and bet against him, robbing his neighbors who bet on Diggs of their land and causing Diggs permanent brain damage.]] This ''might'' be excusable by the fact that Caine implies that [[spoiler:no one expected the drugged Diggs to last so long and take so much punishment]]. But any remaining sympathy Gillon has is thrown out the window when [[spoiler:he threatens to murder Slim Busby unless his brother defeats Honey Roy after catching the two ThrowingTheFight. He remorselessly carries out that promise when Hambone loses, even though Hambone tried his hardest to win.]]
* SignatureLine: Caine's InsistentTerminology about what he does is pretty well-quoted.
--> '''Caine:''' Do you know the difference between a hustler and a good con-man? ... A hustler has to get out of town as quick as he can, but a good con-man - he doesn't have to leave until he wants to.

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