As one of those things I ponder following the end of the show, I ask myself, “How did the Mane 6 fare financially? Who is the wealthiest of them all?”

First, I want to discount Twilight Sparkle. She would’ve inherited the coffers of all Equestria when she ascended the throne, which automatically makes her the richest pony in the world, if not the richest being. I wouldn’t weep for Celestia or Luna, because I’m sure they’re set for several more lifetimes.

Next, on a more imaginable scale, most people would think of Rarity. This isn’t a bad choice. Long before the finale, she had a chain of haute couture boutiques from Ponyville to Manehattan to Canterlot. She might’ve thrown in a few more locations before she finished. Rares was also shown to be successful, as ponies – at least in the bigger cities – shopped her stores.

One thing prevents me from putting her at second, though. Most ponies don’t wear clothes. Rarity’s fashions would be seen by the majority as formal wear only, and how often have you worn your Sunday best?

Therefore, my choice as the next wealthiest pony to the Purple Princess would be – Pinkie Pie. Think about it. She married Cheese Sandwich, who founded and owns a very successful novelty factory. Cheese Sandwich whoopee cushions and gag glasses are sold all over the world, and in this setting, more ponies buy joke items than clothes. Pinkie’s the Melinda to Cheese’s Bill Gates.

Next would be Applejack. Sweet Apple Acres may not be rolling in dough, but I’ll be damned if Twilight wouldn’t cut a deal to make SAA the official apple provider to the crown. Also, I wouldn’t be surprised if AJ insisted Big Macintosh and Sugar Belle be the main proprietors of the farm, as AJ wouldn’t want her niece to go without.

It’s a toss-up between Rainbow Dash and Fluttershy as to who is the least financially successful of the Mane 6. Military personnel, even officers, don’t get paid much, which is why they get so many great deals at restaurants, stores, auto dealerships and such in the U.S.

However, I can’t imagine a nature preserve makes much of a profit, either. Unless she charges ponies to see exotic animals, I’ve no clue how ’Shy makes any bits.

Fluttershy has discord. He could just make money out of thin air, if not then she probably has subsidies from the crown.

Addendum: Each of the Mane 6 are on the Council of Friendship. They probably draw a salary and hefty pension as Co-Rulers of the nation.

Counterpoint to each: Rarity (being the Element of Generosity) gives most of her income to charity, Pinkie probably eats her profits in cupcakes, Applejack is too honest to do what most farmers do these days (cheat on taxes and claim huge government subsidies), Fluttershy is basically an herbal medicine gal (so anywhere from "Scam-levels of moolah", to "just makes ends meet") but she's pretty much confirmed with Discord so her bits are in the infinite number ranges.

Rainbow Dash is a world-famous athlete. Sponsorships alone make her wealthier beyond the dreams of your average pony.

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My bet would probably be:

1. Rarity
2. Twilight
3. Rainbow Dash
4. Pinkie / Applejack
5. Fluttershy

Rarity because she already owned a few prosperous shops, and the ending shows she kept expanding all the ways to Crystal Empire and Yakyakistan.

Twi - because she's a ruler and probably get a nice stipend and has access to the royal treasury when needed. BUT, at the same time, she doesn't own the money.

Assuming she's not a tyrant, then aside from her stipend, she cannot just spend bits from the treasury on wherever she wants without reason. Princess or not, the nobles and even ordinary ponies would eat her alive for something like that.

Dash , because being in the elite squad, probably pays well, plus she gets some cash for every show they perform.

Pinkie /AJ - because their bakery/farm business probably doesn't earn them very much (not saying they're poor, but I doubt they're swimming in bits either).

Fluttershy - because... she's jobless ? I guess she got some stipend for taking care of animals or something.

Of course, since they're all on the 'council of friendship' that probably earns them some cash too...

And when it comes to Celestia and Luna, I think they earned themselves a nice pension for their service (especially Celestia, but since nepotism is magic... ).

Here's the order I would do:

Twilight: She's the reigning monarch, and can levy taxes however she likes. And she can decide to pay herself whatever she thinks the princess of Equestria deserves.

Rarity: Rarity has a high-end fashion empire.

Rainbow Dash: Famous Wonderbolt. She probably has her own awesome fashion line named after her, and tons of merchandise.

Applejack: Applejack probably doesn't have much cash on hoof. Like most farmers, they are cash poor. But AJ has a historic farm house, several acres of rich farm land, and renowned cider that sells out every year.

Pinkie Pie: It is hard to figure out what Pinkie is worth. She is a master baker, and seems to do other odd jobs around town.

Fluttershy: It isn't exactly clear how much money Fluttershy makes, if any, taking care of animals. She lives the most modest of the six.

7035206 I would probably rank Rainbow Dash much higher, because she's not really a 'soldier' and more a world-class athlete performing in a world-renowned team, and also sometimes a soldier historically speaking, plus weatherpony when she's not on duty, and the theory went that she wasn't exactly poor before she was a Wonderbolt either (you seen her pad?).

That out of the way, it's important to separate what they'd have as disposable income and just simple worth. Rarity is probably insanely rich for owning many stores across the world, but if most of that money is sunk into said stores, she might not be as able to spend her cash on stuff as, say, Rainbow Dash, who likely has nothing but money and no capital. Same goes for Twilight; just because her nation Equestria is worth more than all of what the others are worth combined a hundredfold, she might not herself have much disposable income (and that's not counting the idea that the money isn't even hers, but the nations).

In terms of disposable income, I'd probably argue that Rarity and Rainbow are likely in the same ballpark, followed by Twilight. Applejack then comes next, then Pinkie, then Fluttershy (how does Fluttershy make money?!). Yeah yeah, she has Discord, but that's Discord's chaos money, not Fluttershy's. We're separating Rainbow and Applejack so we might as well split the other couples up. If we're not, then I'd argue the Applejack/Rainbow duo might edge out over Rarity, but it's still unclear to me.

In terms of capital and income, then it's probably going to go Twilight, Rarity, Applejack (she does own a massive farm, guys, one that's probably worth quite a lot) Rainbow Dash, then Pinkie and Fluttershy, because chaos illusion currency doesn't come rated by HapHazred. But that's just how I interpret it. It's not hard to come up with reasons why a few of those might be mixed up rather credibly.

Spike

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"How much disposable income do you have?"

"Why would I dispose of my income?!"

"I mean, what do you buy with your money?"

"What's 'buying'?"

Dragon economy.

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7035242 Funnily enough the whole buried treasure pirate thing was because of one pirate who tried to bribe the British Navy with buried treasure locations. If they'd let him go or pardon him he'd tell them where the treasure was buried.

Pretty Big Brain 300+ IQ strat, trying to bribe the wealthiest nation on the planet at the time with some chests of cheap crap, but at least he could console himself knowing that he tried as the brits hung him anyway...

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Huh. And here I always thought it was a legitimate strategy of pirates/smugglers to hide their stolen/ illegal goods when they were anticipating getting boarded and searched by the navy. They'd get boarded and searched, get the all-clear, and then go back and retrieve their goods and be on their way, free of suspicion.

7035246 Ooh, that's good. Perhaps there was more than one reason for burying treasure I'm not aware of?

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Oh, but in the Best Gift Ever special, Applejack actually did had bits on hoof and a lot of it too. She bought a bunch of those expensive dolls, and she still had enough money left for Fluttershy and herself for a train ride. Meanwhile, Fluttershy only bought one doll, but she claims it used all her bits, thus enabling her to have to borrow from AJ. Just something I'd like to add there.

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Taxes for Twilight, the rest of them have jobs

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One headcanon I've heard is that Fluttershy still gets royalties from Photo Finish using her images.

Hmm... Not counting shared income, like mission rewards or royalties on the Journal...

Twilight went from "student stipend" to "Princess Stipend" which probably went up over time, to "the Royal Treasury". I doubt her personal expenditures, however, ever far exceeded the middle-class Canterlot lifestyle she was born into.

Applejack has a share in a farm that I suspect became more prosperous and secure as time went on. Thing about farms, though, is they're cycles - you use the profits from the harvest to invest in next year's harvest as well as tiding you over the winter. So probably not that much ready cash, but it's not like she has expensive tastes.

Pinkie Pie draws a pretty modest salary from the Cakes and only charges for her parties half the time at most, yet somehow never seems short. This has at various times worried both the populace of Ponyville and the investigators of the Royal Mint, but nopony has ever found evidence of things or bits going missing anywhere to match her ready supply. This might have led to more worries, except at this point all involved decided to go home and not think about it very hard instead for some reason.

Rainbow Dash drew a decent salary as weather manager and a better one as a Wonderbolt, but seems to consider it's purpose to be as thourouglhy disposed of as possible by next payday - savings are for old ponies.

Fluttershy had an adequate salary as Animal Manager (seriously, stop calling her jobless!), though not as good as if she'd actually negotiated (in the end Rarity had a few words with Town Hall on her behalf), but there were always needy creatures to spend it on. What personal luxuries she has mostly come from having generous friends, culminating in Twilight arranging a royal grant in perpetuity to fund the Sweet Feather Sanctuary.

Rarity is probably the most finacially-minded of the group, splitting her growing income into various slices after paying her employees. The biggest one is Safe Investments, followed by Good Causes, Business Improvements, Personal Luxuries and Risky Investments. The fact that she still lives a top-drawer lifestyle shows how profitable both her business and her investments are - and if she does it partly on credit, who could ask for better guarantors?

So some of them are well off, some off the scale, and others doing alright. And the ones with money will support the ones without if it comes down to it.

If you run a really successful farm in the real world, you can do very well financially. So I seriously doubt AJ is poor, like some people seem to think.