the main 6 decided to play monopoly, this is the results:
1st Place: Fluttershy as the dog 
Everyone, including Fluttershy herself, was very surprised that she managed to win. The secret to Fluttershy's success was the pink properties. Fluttershy managed to land on all three pink spaces fairly early in the game. She spent as much money as she thought reasonable upgrading her pinks, and everypony kept landing on them. With all the money Fluttershy was earning from Free Parking, Community Chests, and her pinks, it wasn't long before she had hotels. Eventually, everypony got bankrupt at the hooves of Fluttershy's pinks.
2nd Place: Twilight Sparkle as the top hat 
Now this one wasn't quite as big of a surprise. What would be surprising is if Twilight, the master of strategy, came in any place lower. As is common in monopoly, you don't usually land on the same colored spaces. Instead, most ponies just end up with properties from all different sorts of sets. Twilight took advantage of this with her trading. Twilight targeted the poor offering money and the properties ponies needed for the really expensive properties. Twilight made sure to do her trading earlier in game when there wasn't a big risk of getting bankrupt. As ponies slowly started giving her money with her new greens and dark blues; she got enough money to start upgrading. Twilight had made a pretty good living, she had the reds, the yellows, the greens, the dark blues, the railroads, and she even had the browns. She even managed to bankrupt Applejack. However, she didn't have quite enough money to safely upgrade her monopoly’s. She didn't stand a chance with the thousands of dollars and hotels that Fluttershy had. Eventually, Twilight had spent too much money on upgrading in an attempt to catch up to Fluttershy. In the end, it only made her easier to bankrupt.
3rd Place: Pinkie Pie as the thimble 
Pinkie Pie… she… I, I don’t even know where to start. I’m not sure what I expected from Pinkie, but it wasn’t this. So, what happened was Pinkie got zero properties. The entire game, she didn’t have a single property. It wasn’t because she was too stubborn to buy one. It was because she literally never landed on any. The entire game she avoided landing on any unowned properties. I’m not sure how, but the dice always made sure she was either on Go, on a Chance or Community Chest, on Free Parking, visiting jail, in jail, or on an owned property with very low rent. She never really got the chance to earn or lose very much money. If she went to free parking, somepony already beat her to it. If she lost 20 bucks on a property, she’d just get it back with a chance card. During one part of the game, Pinkie managed to land on the very last unowned property. However, Twilight had beat her to it the turn before. Eventually it was only Pinkie and Fluttershy left. But Pinkie refused to land on any hotels, or anything that would make her lose a large amount of money. After a while we decided to stop waiting for Pinkie’s luck to run out. Fluttershy was declared 1st place and Pinkie was declared 3rd; we felt Twilight deserved 2nd more than her because Pinkie didn’t really contribute anything to the game. So in the end Pinkie didn’t really do much except give everypony a lot of laughs. Which is very fitting for her.
4th Place: Applejack as the wheelbarrow 
Applejack lost because of her stubbornness. She had four properties. Two reds and two yellows. Applejack was pretty poor, not as poor as Rarity or Dash, but still pretty poor. Twilight had the last red and the last yellow. Twilight kept offering her money and the red property for the two yellow properties, but Applejack was too stubborn to give Twilight any properties. A little after Rarity and Dash got bankrupt, Applejack was really low on money. AJ eventually gave in to Twilight’s trade. However, the money Applejack earned wasn’t enough to save her. She got bankrupt by Twilight the turn after the trade.
5th place: Rainbow Dash as the racecar 
Dash lost because of bad luck and desperation. Dash was doing okay on money and she had two orange properties. Dash had landed on quite a few money losing spaces and had about $800 left. That was when Twilight landed on the last orange space and bought it. All the other spaces had already been bought and Dash was really desperate for that last orange. Twilight took advantage of the situation and set the price for the last orange to about $600. Dash agreed to the trade because she knew that she didn’t have a chance at winning if she didn’t have at least one monopoly. Dash prayed to Celestia that she would get to pass Go before landing on any dangerous spaces, but it was in vain. She landed on Fluttershy’s most expensive hotel and got bankrupt easily. One funny thing that happened was that Dash kept getting doubles and going to jail over and over again for speeding.
Absolute last place 6th: Rarity as the Iron 
Rarity lost from being cursed and unlucky. For the first half of the game Rarity could have sworn she was cursed. She landed on literally every single space that Pinkie landed on. When Rarity finally managed to stop following Pinkie, she managed to land on a railroad, a water works, and a light blue space. Rarity then got the other two light blues through trading; but she became extremely poor afterwards. Rarity had very horrible luck and she kept landing on spaces with houses. Rarity had to do a lot of mortgaging and trading for money to survive. After a marathon of landing on bad spaces, Rarity had only two light blues left and $1. That was when she landed on Fluttershy’s newly placed hotel. Rarity snapped. She didn’t even try trading her spaces for money. Instead, she got up, threw her hooves in the air, and declared with a shout “I HATE THIS GAME!!!” She then ran off back to her boutique and to her secret ice-cream stash.
