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A Recursive Fanfiction of The Life and Times of a Winning Pony, Chengar Qordath's My Little Pony: Friendship Is Magic fanfic, The Freeport Venture follows the misadventures of Sunset Shimmer after she flees Celestia and Equestria and winds up in the lawless island city of Freeport. There, she seeks to make a name for herself as a powerful mage — and, perhaps, an alicorn — in her own right, while also contending with the threats and complications that come with being Freeport's only certified wizard-for-hire.

The currently published stories, in publication order, are A Moment in the Sun, The Freeport Venture, More Equal than Others, Auction Night, The Hunted, A Thousand Masks, Blood and Iron, Shimmer-Mare's Birthday!!!, Blood Debts, Come and See and Northern Venture.


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Tropes in this work include:

  • Asexuality: Implied in Sunset's case. Strumming points out how she had never been interested in boys or girls as far as they knew, despite having gone through the phase where most ponies go gaga for girls/boys.
  • Adult Fear: In The Hunted, Kukri’s parents have to deal with the fact that there’s something that can pass any defense, is unhinged at best and actively sadistic at worst, has very likely ties to someone who wishes their family harm, and seems to have a marked interest in their eleven-year-old daughter.
  • All Trolls Are Different: In Come and See, Heritor Azurite's palace is guarded by enormous ice trolls. Going by the description, they resemble fairly typical mythological trolls, with shaggy hair and thick fat to ward off the cold.
  • An Arm and a Leg: One of Sunset's front legs after the battle against Blackfyre.
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  • Artificial Limbs: Sunset gets one after her leg got royally messed up by Blackfyre.
  • Base on Wheels: In Come and See, Heritor Azurite has a mobile crystal fortress pulled by a hundred yak thralls. Its mobility means he can move it to reinforce whatever battle he needs to be at, while also making it impossible to attack it with conventional siege weaponry.
  • Badass Bookworm: Sunset definitely qualifies. She's well-read enough to identify most magical threats at a glance, and, though she can be naïve about the real world, she more than makes up for it with sheer magical prowess. By Freeport Venture: A Thousand Masks, she has worked up enough of a reputation to scare of at least a dozen guards with a mere threat.
  • Bad Future: First discussed in Blood and Iron, before being explored in the side-story Come and See. In the timeline where the war against Sombra takes place, Sunset Shimmer (before she becomes a lich and renames herself Magus Rising Fire) successfully convinces Freeport to join the conflict and helps Equestria turn the war around... only for the events told in Blood and Iron to occur.
  • Black Magic: Mind control and necromacy are specifically stated to be illegal black magic. Unlike other cases, black magic here is not stated to be inherently corruptive or addictive — rather, it’s more of a case of Slowly Slipping Into Evil, since dark magic provides such quick, easy, and (at first) cost-free options, it becomes too tempting to indulge in to resist.
  • Breather Episode: Freeport Venture: Shimmer-mare's Birthday. The two sequels revolved around, respectively, an undead monster hunting a child for being a Free Mind and an attack by time-traveling necromancers. This is a story about a child panicking over being unable to find the perfect gift for her mentor.
  • Cool Sword: Chainbreaker, the legendary sword wielded by a revolutionary leader from Freeport. It's sort of deconstructed, in that though it has some enchantments, and it's even hinted that Sunset may have some natural or supernatural claim to it, but without the proper training or arcane knowledge, it's just a historically significant sword, no different from a sword you could find in the present day.
  • Curb-Stomp Battle: In A Thousand Masks. Strumming and Puzzle are pinned down. At least a dozen guards are between them and the exit, with a bunch more rapidly closing in. Then Sunset the hired muscle arrives. It's not even a battle, she just casually points out that the Mooks are carrying pouches with very flammable alchemical substances, and they decide to high tail it out of there.
  • Curse Cut Short: In Blood and Iron, the bokor doesn't get the chance to get past the first letter of his curse, but the rhyme makes it clear what he meant to say.
    "You didn't even tell me what you want!" the bokor snarled through a heavy accent. "You have some nerve attacking my home, you upstart c—"
  • Demoted to Extra: In Freeport Venture: Shimmer-mare's Birthday, everyone but Kukri and Sunset are demoted. Puzzle and Strumming both only play a minor role, with only a few lines each.
    • Reversed in A Thousand Masks. Strumming and Puzzle take centerpiece. Kukri is only indirectly mentioned as Sunset's apprentice, and Sunset herself only serves as muscle backup to the love doves' stealth mission. She does get her Big Damn Heroes moment by scaring of at least a dozen guards (several armed with primitive firearms) solely with empty threats.note 
  • Dark Is Evil: In Freeport Venture: The Hunted, Kukri swiftly develops this view, since the Monster prefers to attack in the dark.
  • Dramatic Irony: The Equestrian Intelligence Service intends to keep tabs on Sunset on the off-chance she might go off the deep end and, say, return to Equestria as a false alicorn at the head of an army of brainwashed minions or something like that.
    Sunset Shimmer: "Yeah, there’s no way that would ever happen."
  • Eldritch Abomination: The demon in Freeport Venture: Auction Night is positively Lovecraftian.
    There were tentacles. There were claws. There were gaping mouths full of needle-like teeth. And none of them were arranged in anything remotely resembling natural or sane anatomy.
  • Elemental Embodiment: Numerous elemental spirits appear, and in their natural state they seem to be formless beings inhabiting their native element, but can adopt and maintain physical form as long as they're in contact with their element. They're usually seen when they've been bound by magic to serve as magical security systems, such as a wood spirit bound within a door or a stone spirit in a wall. So far, stone, air, wood, water and metal spirits have all appeared or been mentioned.
  • Even Bad Men Love Their Mamas: The feared pirate Metal Mome was apparently rather fond enough of his mother, Granite Mome, to name his ship, the Granite Heart, after her. Insulting his mother is also one of the few ways to get him visibly pissed.
  • Eye Scream: Inflicted on Starlight by Sunset.
  • Famous Ancestor: Discussed and ultimately deconstructed in Northern Venture. Even if Sunset was related to a famous Freeport revolutionary leader, something very unlikely, it wouldn't mean much. Taking his last name would just seem like a power play, and even if she found irrefutable proof, most of Freeport would deny it or just not care.
  • Foil: Starlight Glimmer is one of sorts to Sunset. Both are very powerful unicorns, both are extremely dedicated to a goal (equality or alicornhood) and won’t shut up about it, and both have gone back on their ideals when faced with imprisonment (Starlight using her family’s wealth and connections, Sunset using dark magic). The main difference is Sunset is more aware of her failures and much less of a hypocrite.
  • Future Me Scares Me: The necromancer in Blood and Iron is heavily implied to be Sunset Shimmer from an alternate future, which is later confirmed in Come and See. Said character isn't too fond of this notion, preferring to believe that the nercomancer was just insane.
  • Half-Human Hybrid: Ponies and griffins can interbreed to make hippogriffs. Zyphons are specifically zebra-griffin hybrids.
  • Handicapped Badass: Sunset becomes this after losing her leg.
  • Healing Factor: The Monster has one. It only works as long as its target is afraid of it.
  • He Who Fights Monsters: It’s mentioned that warlock hunters are the likeliest demographic for becoming warlocks themselves.
  • Kill It with Fire: Ice trolls turn out to be rather vulnerable to pyromancy, as the thick hair and fat they use to ward off the cold are both highly flammable.
  • Mage Tower: Sunset ends up building one made of obsidian to live in in Freeport, partly because it’s traditional, partly because it means she has to buy less land.
  • Mind Rape: Most forms of mental magic edge at least somewhat into this. For a specific example, in The Freeport Venture there’s Sunset destroying Metal Mome’s mind and reducing him to a permanent vegetable state.
  • The Nicknamer: The independent changelings/Free Minds are a bit odd about names, and prefer to use titles or nicknames on most occasions. They refer to themselves as "this one", other Free Minds are some variation of "the other one", Chrysalis is "the Old Mind", ponies are nicknamed with constructs of their name and gender (such as "the Shimmer-mare" or "the Heartstrings-mare"), and Celestia is "the White Pony".
  • Not-So-Safe Harbor: Freeport, run by greedy merchant-princes and with guards so corrupt they are expected to supplement their income with bribes, is a notorious haven for Black Market deals in every sort of banned good, a hotbed of espionage and counterespionage, and a nest of organized piracy.
  • Only the Chosen May Wield: Zigzagged. It does have some enchantments, and it's hinted that Sunset may have some claim to it, but even without the proper arcane knowledge or claim, anyone can still use it as a sword.
  • Things That Go "Bump" in the Night: The Monster in Freeport Venture: The Hunted. Numerous species of such beings are stated to exist.
  • Tome of Eldritch Lore: The Black Codex, written by a cabal of warlocks and lunar cultists during the Lunar Rebellion and containing information on every form of Black Magic in existence.
  • Revenant Zombie: The skeletal revenant of a pegasus with metallic wings appears in Blood and Iron as an elite soldier in the undead horde. Besides being self-aware and able to talk, it is an extremely fast and agile flier, and is single-mindedly obsessed with killing Starlight in revenge for Starlight having killed her friends. In life, it was the Rainbow Dash from the Sombra timeline seen in "The Cutie Remark", which was retconned out of existence by Starlight and Twilight, and was part of a small group of "survivors" who went to the "main" timeline for revenge.
  • Shout-Out: One of the perks Strumming lists for being a spy is the right to be really snooty about ordering your milkshakes shaken, not stirred.
  • Slavery Is a Special Kind of Evil: Slave-owning and the slave trade are noted to be some of the few activities to be completely illegal in Freeport, a city that otherwise fully deserves its reputation as a Wretched Hive. Though you could most likely convince a constable to look the other way with a well-placed bribe.
  • Slowly Slipping Into Evil: Black Magic works this way, rather than being actively addictive: at first, a pony might use dark magic to escape an otherwise hopeless situation, then maybe use it in another dangerous or desperate moment, eventually using it more readily and more often, without necessarily realizing what’s happening. Eventually, it starts becoming their preferred recourse to issues, and by then there’s no turning back.
  • The Undead: Mutiple varieties of undead exist, including basic zombies and skeletons (mindless corpses controlled by necormancers), draug (feral undead created from the bodies of drowning victims), revenants (intelligent if single-minded undead obsessed with righting wrongs they suffered in life) and liches.
  • You Killed My Father: In Blood Debts, the zebra who tried to assassinate Strumming did so to avenge the death of his uncle, the bokor Strumming murdered in Blood and Iron.
  • Weakened by the Light: Direct sunlight interferes with necromantic energy, and as a result undead creatures are weakened (or in some cases outright destroyed) by being exposed to daylight or daylight-based spells.
  • Wretched Hive: Freeport is a Not-So-Safe Harbor ruled by greedy merchant-princes, its guards are so corrupt they are actually expected to supplement their income with bribes, most people prefer personal blood feuds to get “justice” anyway, and it’s a haven for mercenaries, spies, and legalized piracy. There’s a fairly good justification for why a major port city is allowed to go on like this — it sits on an archipelago right between Equestria, Gryphonia, and Zebrica, meaning none of the nations can make any move on it without the other two seeing it as a threat.

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