The story so far  
When the prohibition started, Octavia was forced out of the pubs she used to perform in, and thrust into the criminal underworld of cider smuggling.
 
Act I:
 
Ambushed by Lyra and Bon Bon, Octavia found herself smuggled off to Manehatten to be disposed of, overcoming a her own mental battle while unconscious. Meanwhile, Vinyl Scratch was lured back to Ponyville, chased by hitponies, and finally cornered and fed false information to convince her that it was Octavia who wanted her dead. Reluctantly, she joined Lyra and Bon Bon in the Flim Flam Mafia, convinced it was the only way for her to survive, while meanwhile her (now former) friend was being sent to a watery grave in the bays of Manehatten.
 
The characters
 
The Apple Family
 
Octavia, Tavi - A runner, and sometimes hitmare, for the Apple Family, as well as our anti-heroine. Shes very cold, efficient, and possibly on the edge of insanity, considering she often hears voices in her head. Shes very detached from most everyone she works with. Her weapon of choice is a classic Thompson submachine gun, though she longs for a time when she wasnt caught up in the underworld.
 
Applejack, Jack - Leader of the Apple Family Mafia. For as serious and intense of an individual she is, shes quite merciful and honorable for a mob boss. In a fight, quite capable in her own right. Threats and promises alike are always kept. Her .45 long Colt is always on her.
 
Big Mac - Big Mac is the muscle when its needed, and often oversees shipments himself. Hes clumsy under pressure, but tries to play safe. Hes incredibly hard to stop in a fight, often getting in close to use a lever action shotgun.
 
Applebloom - Applebloom is constantly watched over by the Family. Though shes known to have affiliations, no one dares touch her for the wrath that would be incurred shortly thereafter. Shes actually quite sneaky, and acts as a set of eyes for the Family.
 
Nautical - A former navy officer, now a smuggler in the Manehatten branch of the Family. Hes very rough, and often disagrees with decisions made by the Family, but carries them out without hesitation.
 
The Oranges - The Oranges are much more white collar in their crimes, and finance a majority of the Apple Family operations right out of Manehatten. Their covert, widespread control has led to an easy life in their hometown, and few conflicts from rival mafias.
 
The Flim Flam Mafia
 
Lyra, Heartstrings - Lyra is Flim and Flams top hitmare. Shes evidently got a history with Octavia back from their days as musicians, as well as a grudge. Perhaps thats why she went to such great lengths to screw with Octavia and manipulate Vinyl Scratch? Regardless, Lyra is very calculating and vicious, and doesnt care who she harms to get her way.
 
Bon Bon - Bon Bon (jokingly sometimes referred to as Don Bon) is Lyras partner. She is a lot more patient, manipulative, and persuasive, offsetting Lyras hotheaded, careless attitude, but can be just as vicious, if not more so than her partner.
 
Flim and Flam - The notorious twin brothers who are in charge of the rival mafia. Theyre rarely seen up front, but are known for being incredibly hasty, which has resulted in innocent bystanders being hurt, and reduced control in Ponyville.
 
Trixie - Another of Flim and Flams hitmares. Little is actually known about her, other than shes very good at getting around, and is very charismatic
 
Ponyville PD
 
Twilight Sparkle (Badge 1247) - Twilight Sparkle is hell bent on purging corruption from Ponyville, yet so far has been unsuccessful in pinning the Apple Family with any crimes.
 
Pinkie Pie - Twilights partner, though not the most trustworthy shes easily bribed and has frequently hidden evidence right under Twilights nose, leading her away from the Apple Family.
 
Other Appearances
 
Pirate Dash - Pirate Dash is a loyal customer to the Apple Family, frequently relying on them to supply alcohol to her crew.
 
Vinyl Scratch - A lot has changed, hasnt it? She always was a little on the naive side, and was a bit reckless. What turned into a mission to find her long lost friend turned into a fight for her own survival.