History YMMV / Diggstown

* SignatureScene: The movie has no shortage of memorable scenes, but the SugarWiki/MomentOfAwesome final bout is probably the hardest to forget. [[spoiler: Roy narrowly defeats the tenth boxer, a SuperRinger who beat him twice when he was in his prime, only for Gillon to use some painstaking LoopholeAbuse to make the exhausted Roy fight ''another'' boxer. That boxer is an undefeated fighter brought in from the nearby prison who is established as a known enemy of Caine's in the first scene. Then, just as the fight starts, Caine conspicuously has that ringer throw the fight, revealing that the other boxer was never his enemy and he's been manipulating Gillon and the corrupt warden into picking that man as a ringer from the first scene of the movie.]]

* MoralEventHorizon: Boss Gillon is a CorruptHick, 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.]]

* 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 [[CorruptHick 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.

* MoralEventHorizon: Boss Gillon is a CorruptHick, 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 executable 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.]]

* 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 [[CorruptHick 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 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.

* AwesomeMoment: Caine's final con against Gillion.

* CompleteMonster: John Gillon, all the way. He tried fixing the last fight of Charles Macom Diggs by betting against him while the whole town bet on him, and when Diggs wouldn't go along, doped his nasal spray, which essentially turned his brain into a vegetable. And that's not even mentioning what he does to [[spoiler: Slim after Ham loses his fight with Roy]].
-->'''John Gillon:''' (''after Caine has made him bet his entire fortune'') Sounds like you know quite a bit about me, Mr. Caine.
-->'''Gabriel Caine:''' What I know about you, Mr. Gillon, would make Charles Macom Diggs himself stand up and walk.