Perhaps the Capo retired recently, and he was more of a community style guy who asked for 'donations' but plowed it back into the neighborhood, and his successor has become more violent and greedy? Giving them an avenue to find the retired Capo and talk to him?
I'm thinking having a bunch of rival bosses, each controlling a turf in different parts of Manehattan. Some names for you:
Little Seedser (should be obvious)
Don Coltleone, a.k.a The Godstallion (again, beyond obvious)
Based on real-life mobsters:
Dapper Dock
Double Dutch
Lucky Strike
Thrillson Risk
Cutting Board (a cookie for anybody who can guess the inspiration for this one)
Bumpy Road (a cookie here too)
For those of you who think this is a bit dark to be playing with a 9 year old kid, the comics have established that intimidation and extortion do indeed happen in parts of Equestria. Not quite as idyllic as shown on the TV show.
And FYI this is a kid who in one of our previous games insisted that Celestia face an ultimatum where she had to eat a potentially lethal poisonous mushroom.
cheers,
Gabe
EDIT: and how could I forget? Pony Contralto