In terms of major comedowns, which would you say is the biggest in the bright and breezy world of Equestria?
Discord, perhaps? One minute he's happily filling the sky with chocolate-milk sodden cotton candy clouds, and blissfully herding packs of long-legged rabbits around, next he's a stone statue being regularly excreted on by feathered 'friends'. Oh dear.
Princess Luna, maybe? She had a pretty cushy job as a princess whose only real task was raising the moon every night, but jealousy and bitterness caused her to turn into Nightmare Moon. It must've come as a big shock to be stranded on a barren rock for a thousand years afterwards. Oops.
There are probably quite a few other individuals I could mention too, who sometimes through sheer selfishness, cruelty or other negative reasons end up losing everything precious to them. It's not an uncommon occurrence, which is why you should always be good and kind (or kind and good, the order doesn't really matter).
For my bits though, the most ignominious of declines has to belong to a magenta mare currently residing in a grotty motel room, slap bang in the dodgy end of Ponyville. And yes, there is actually a less appealing side to that place... there are just some things the producers would rather not show you. Did you really believe it was all small-town charm and pretty pastel colours? Geez, talk about naive!
Let me take you to a locale where the wallpaper peels, the damp rises and the toilet is forever blocked with who-knows-what. Instead of joyous songs of friendship, cries of woe can be heard all night outside, as another hapless victim is mugged of their paltry possessions. Garbage swirls through the air like dandelion seeds, edible food is scarce and if Rarity saw the tawdry rags most of the populace are attired in, it would take more than smelling salts to revive her traumatised, comatose form.
...And it is now headlong that we dive into this distinctly insalubrious community to meet the very last pony you'd expect to be dwelling there. A proud mare at heart, she'd previously been used to only the finest things in life, on account of her long term marriage to the town's premiere tycoon.
When she was his lady, she could get away with such minor indiscretions such as firing minimum wage staff at will and pushing in first place at the local spa. In her glory days, she even had a willing miniature protege to mold in her 'beauteous' image, and until a few short months ago, everything was truly perfection.
Alas and alack though, it wasn't long until things began to go pear-shaped. Or 'Apple-shaped' as the case may be, considering the identity of the leader of those accursed Cutie Mark Crusaders. They seemed to do nothing but gallop around the town all day, smashing it up (whilst still being loved for it) under the vague pretence they were trying to discover their 'destiny'.
Well they certainly did that, and a lot more besides. Like start the countdown to my downfall, when they brainwashed my own progeny into betraying and berating me publicly. And then, those parasites were 'rewarded' for ruining my life afterwards with their Cutie Marks! It isn't fair... The current occupant noted sourly, as she lit yet another candle to preserve what meagre vestiges of light remained in her squalid room due to the electrics being out again.
After Diamond Tiara's unseemly scene right outside the school where she'd worked so diligently as head of the board, things went from bad to worse to downright catastrophic. That old fool Filthy seemed to take heart from their daughter's unexpected rebellion, and began displaying an irrational side that she'd never seen before.
Terms like 'credit limit' and 'co-operative decisions' started being bandied about, and she lost a lot of her previous freedom as Filthy decided to stay home more often 'to see my darling daughter grow up'. What did he need to do a thing like that for? I already had Diamond totally under my control, his sole purpose was to go out and make more money for me to generously redistribute among international merchants. Or spend frivolously and freely in Canterlot, either explanation works.
Regardless, with the purse strings tightening and her iron grip on power rapidly loosening, both at home and in school, you'd think this tortured soul would reconsider her outlook on life a bit. Maybe tone down some of her incessant demands, learn to respect her filly's wishes to be more independent and treat her partner like a true equal instead of a walking wallet to be opened on command.
Not a bit of it. Not only did she fail to alter a single aspect of her incendiary nature, she actually doubled down on the numerous factors which made her to repellant to other equine lifeforms.
She specifically refused permission for Diamond Tiara to see her new friends, and threatened to take her crown away if she didn't 'return to her old tolerable self'.
She told Filthy she'd require triple the weekly budget she'd had before, as ponies who used to tremble with fear at her name now simply stared down their muzzles with contempt. A whole new exotic wardrobe was the answer, to demonstrate to those penniless paupers their proper place.
The last of many straws finally came during a meeting to discuss said financial arrangement. In the middle of a heated argument, in which Filthy's somewhat salient point was, because he brought in roughly 100% of the family's income, he should perhaps have a little more jurisdiction where it went, she'd made a little humorous aside.
She couldn't remember her exact wording, but it'd been something along the lines of 'Well, if you're so worried about spare cash, why don't you sell that useless old fossil Randolph to the glue factory in Phillydelphia? It's all he's good for these days after all.' Pretty hilarious, I'm sure you agree...
...And even more so because the aged retainer himself was currently within a few feet of her at the time, refilling her and his master's coffee pots. From her perspective, his subsequent tears and pathetic dash off down the corridor to cry were absolutely hysterical, and a nice bit of light relief from the ongoing squabble.
Funnily enough however, Filthy didn't quite find the callous mocking of the loyal servant who he'd known since he was a young colt quite so amusing. In fact, considering the devoted butler had helped him deal with everything from minor owies to overcoming the sudden tragic death of both his parents (much more than his wife had ever done) you might say it got him a bit hot under the collar.
Except, he wasn't wearing one at the time. Whether this was because he thought his betrothed was capable of stealing it off his back when he looked the other way is entirely speculation.
Anyway, after that thoughtless quip, it was safe to say our mare protagonist came out of the debate with a lot more than she'd bargained for.
No, not the extra money she'd been after. Instead, all her past and future bits were currently being shared among the hard-working staff there by means of a massive raise, with the long-suffering Randolph of course receiving the main percentage. It'd made him so happy, all thoughts of his mistress's undeserved abuse completely left his head, and he'd turned multiple joyful somersaults right there in the stairwell.
Randolph would have much more manoeuvrability to perform such acrobatic gymnastics soon too, as he was instantly to be located to a sleeping chamber roughly ten times the size of his old shoebox of a room. When he'd deigned to ask Filthy how such a thing'd been possible (the mansion wasn't quite as big as it appeared on the outside) the smirking tycoon replied that he'd been having a bit of a 'clear out', and in the process somehow found enough space to not only upgrade Randolph's living conditions, but the other servants too.
Yeah, by throwing out or donating to charity all the trinkets and treasures I'd purchased over the years. Who cares if I barely even gave most of them a second glance, they were mine and he had no right to do that! Our 'heroine' mulled angrily in her tiny, greasy kitchen, whilst attempting to make a... what was it the common folk called this thing again... a sand-witch? Let's see... do you put the bread slices side-by-side or back-to-back like this? And how On Equestria do you get the fillings in?! Phew, this is far too strenuous work for me. Time for a little rest...
Feeling very sorry for herself indeed, our starving mare collapsed exhausted onto her unmade lumpy mattress to briefly surmise the rest of the series of unfortunate events that'd led her to this dire predicament. Yeah, I came out of that confrontation with my ex-husband with 'more than I bargained for' alright... namely a bunch of divorce papers and a day in court. I-I lost everything in one go... never have I seen a judge more biased than Celestia was back there! She didn't even ask if I had any witnesses to speak on my behalf! W-well, it's not as if I was able to find any, and I wasn't about to waste money by bribing anypony to say they liked me, but still! It's the principle of the thing!
And now, from being the 'toast of the town' in social gatherings to a helpless recluse in a drab bug-infested cubicle living from hoofout to hoofout, her slide into irrelevance and humiliation was finally complete. Unceremoniously sacked from her job once the full facts of her rampant mistreatment of foals became public knowledge, she now survived mainly on the kindness of others... the sort of selfless altruism which she'd blatantly lacked when having a full belly and wallet. Some might call it karma, she just thought it was a nuisance.
If pride truly does come before a fall, I must've plunged so far down from the sky there's a life-size impression of me on the ground now, she told herself sadly, imagining what such an outline would look like, curved nose and all. And what makes it even worse, is its Hearth's Warming Eve today. No illustrious parties to attend, no flashy outfits to show off to the glitterati, no seasonal decorations to hang up, no family to spend i-it w-with...
As quickly as she'd collapsed onto her uncomfortable excuse for bedding, she forced herself up whilst frantically dabbing around her eyes. H-Hang on just a second! What is this unwanted fluid coming from my eyes?! After the way my skinflint husband and my treacherous daughter have treated me, they don't deserve my tears! I don't need their help, and I certainly don't need their love! I'll find my way back to the top again, mark my words! I don't care who I have to seduce or marry to get there, just as long as it's an elite standard of living about equal to what I had before! ...Well, alright then, maybe I can do without a few essentials, such as my own personal masseur and fresh strawberries five times a week, but that's a sacrifice I'm willing to make! For I... am brave! I... am bold! I... am Spoiled Ric...
Knock knock!
An unexpected rapping at the door put a premature end to the humble mare's self-aggrandising, and considering the rather unsavoury ghetto she was forced to reside in now, Spoiled's anxious thoughts rapidly turned to the worst case scenario.
Oh no, what happens if it's some uncouth hoodlum wanting to take 'advantage' of my situation? Even if I ignored him, that flimsy door could easily be broken with a strong kick. Or it might be my crazy neighbour, who keeps asking to borrow ice every hour. I told him again and again the machine is broken, but he just doesn't listen! I do wish he'd stop head-banging the wall late at night too, it's difficult enough to sleep in this rat's nest as it. I suppose I should go and see who it is, before I worry so much an extra frown mark appears on my forehead. Oh, why didn't I find space for anti-aging cream in my cardboard box before leaving Rich Mansion? Stupid, stupid, stupid!
Fortunately, one of the few modern amenities this otherwise wretched dump had was a peephole so you could see exactly who your visitor(s) were. Spoiled naturally took full advantage of this, though not without giving it a thorough wipe-down first. Hygiene, you understand.
W-What? I-It can't be them! T-they should be celebrating Hearth's Warming by now, and the joyous way they reacted when I left... no, this must be some sort of immature prank, or a false delusion brought on by hunger! I'm going to open it up now, and get to the bottom of this...
Wasting no more time, Spoiled took the initiative by flinging her front door wide open... but as it turned out, her first view as to who was outside was completely accurate.
For standing there, having travelled all this way and yet still in his well-tailored work clothes, was none other than the newly single Mr Filthy Rich. Loitering around nearby him, obviously not entirely pleased to be present, was a very surly Diamond Tiara.
"Hello, Miss Milk." Filthy said pointedly, his monotone voice free of any emotion. "I believe we have a few important things to discuss. May we come in?"
Author's Note
This'll be a two-part fic, so expect the next one soon-ish. 
And no, before you ask, Spoiled and Filthy are not getting back together, in case you missed what Filthy said at the end there. 
