Founders of Equestria

Princess Platinum, Clover the Clever, Commander Hurricane, Private Pansy, Chancellor Puddinghead, and Smart Cookie are six ponies who first discovered and founded the kingdom of Equestria long before the series' present day. Platinum, Hurricane, and Puddinghead served as the leaders of the unicorn, Pegasus, and Earth pony tribes respectively, and Clover, Pansy, and Smart Cookie were their advisors/second-in-command.

Design and development
Commander Hurricane's cutie mark, according to illustrations in The Journal of the Two Sisters, matches at least the design of those of Compass Star and "Ponet".

Clover the Clever is named similarly to the G2 Earth pony boy Clever Clover.

Depiction in the series
The Equestrian founders' story serves as the focus of the season two episode Hearth's Warming Eve, reenacted through an annual holiday stage pageant. Long ago, before the rule of Princess Celestia, Earth ponies, unicorns, and Pegasi were divided by hatred and only cared about their own tribe. The tense peace between the pony tribes is eventually broken by a mysterious blizzard.

Princess Platinum of the unicorns, Commander Hurricane of the Pegasi, and Chancellor Puddinghead of the Earth ponies hold a summit to figure out how to cope with the blizzard, but they are unable to reach an agreement. After the three leaders confer with their subordinates—unicorn advisor Clover the Clever, Pegasus Private Pansy, and Earth pony secretary Smart Cookie—they decide to set out and find a new land.

The three pairs all meet in the same location and argue over whom has first stake over the new land, causing another blizzard to start. The six ponies take shelter in a cave, but as Puddinghead, Hurricane, and Platinum continue to argue, they are soon frozen in ice. Clover the Clever identifies the cause of the blizzard to be windigos—winter spirits that feed on hatred.

Despite the animosity between their leaders and tribes, Smart Cookie, Pansy, and Clover maintain warm relations, and they eventually break the windigos' spell through the Fire of Friendship. Their warmth thaws their leaders' bodies and melts their hearts, and the leaders decide to share the new land, naming it Equestria.

In the season five episode Hearthbreakers, the Friendship Express train offers "Chancellor Puddinghead puddings" to passengers.

IDW comics
The Hot Topic cover features Fluttershy as Private Pansy.

Chapter books
In Twilight Sparkle and the Crystal Heart Spell, Rainbow Dash mentions Commander Hurricane in chapter 9, "A Head in the Clouds".

In Princess Celestia and the Summer of Royal Waves, Princess Celestia mentions Clover the Clever, referred to as male, in chapter 5, "Lesson Number Fun".

In Princess Luna and the Festival of the Winter Moon, Princess Celestia mentions Chancellor Puddinghead in chapter 11, "Royal We".

My Little Pony (mobile game)
In Gameloft's mobile game, the Mane Six can dress up like the Equestrian founders through the Pony Editor minigame.

The Journal of the Two Sisters
In Amy Keating Rogers' The Journal of the Two Sisters, the Equestrian founders are mentioned frequently in Celestia and Luna's journal entries. Smart Cookie, Private Pansy, and Clover the Clever act as representatives of Star Swirl the Bearded and approach Celestia and Luna to be princesses of the recently founded Equestria.

When Celestia and Luna finish constructing their castle, they meet King Bullion and Princess Platinum of the unicorns. Platinum acts disrespectful to Celestia and Luna at first and calls them "blank flanks". After Luna pulls a prank on Platinum, she apologizes for her behavior, and the three princesses start over as friends.

Private Pansy, Smart Cookie, and Clover the Clever also become victims of Luna's pranks, but Chancellor Puddinghead outsmarts her. Due to Celestia and Luna's influence, Puddinghead makes better leadership decisions, and Commander Hurricane learns to control his short temper. Hurricane also helps settle a dispute between ponies and griffons.

Merchandise
The Equestrian founders are featured on cards in the Marks in Time expansion set of Enterplay's collectible card game.

In Matthew Reinhart's pop-up book My Little Pony: The Castles of Equestria, the real Chancellor Puddinghead, Smart Cookie, Princess Platinum, and Private Pansy are depicted on pages 5-6 in a pop-up of the Castle of the Two Sisters.

Princess Platinum
Princess Platinum is the leader of the unicorn tribe and the daughter of the Unicorn King Bullion. She is portrayed as considerably snobbish, viewing the other pony tribes as inferior to unicorns and treating Clover the Clever like a servant. Rarity plays her in the Hearth's Warming Eve pageant.

Enterplay collectible card game Marks in Time expansion set card #45 C of Princess Platinum gives her the description, "Princess Platinum had no idea that moving to Equestria, where gems are incredibly common, would drive the prices of jewels down so low that they're hardly worth more than several bits a piece."

Clover the Clever
Clover the Clever is Princess Platinum's royal advisor and Star Swirl the Bearded's apprentice. Twilight Sparkle plays her in the Hearth's Warming Eve pageant.

Enterplay collectible card game Marks in Time expansion set card #33 C of Clover the Clever gives her the description, "As Star Swirl the Bearded's personal apprentice, Clover the Clever had access to many magic spells early in their development that would go on to become staples of sorcery. Ponies like Twilight Sparkle still study these spells to this day!"

Commander Hurricane
Commander Hurricane is the leader of the Pegasus tribe and the Pegasus Weather Brigade. He is portrayed as very short-tempered and having a militaristic manner of speech. Rainbow Dash plays him in the Hearth's Warming Eve pageant, in which he is referred to as female in the pageant's context.

Enterplay collectible card game Marks in Time expansion set card #6 C of Commander Hurricane features the quote "This! Is! PEGASOPOLIS!"

Private Pansy
Private Pansy is Commander Hurricane's subordinate. She is portrayed as being soft-spoken and harboring a secret and extreme dislike toward her superior. Fluttershy plays her in the Hearth's Warming Eve pageant.

Enterplay collectible card game Marks in Time expansion set card #56 C of Private Pansy gives her the description, "Pansy never rose above the rank of Private. Since she usually preferred playing with cute little bunnies and squirrels rather than shining her armor, it was probably for the best."

Chancellor Puddinghead
Chancellor Puddinghead is the elected leader of the Earth pony tribe. She is portrayed as being very eccentric and random, such as trying to read a map with holes in it and having no concept of up or down. Pinkie Pie plays her in the Hearth's Warming Eve pageant.

Enterplay collectible card game Marks in Time expansion set card #23 C of Chancellor Puddinghead gives her the description "Chancellor Puddinghead is famous for thinking inside the chimney, barking up the right tree, and going on the deep end."

Smart Cookie
Smart Cookie is Chancellor Puddinghead's secretary. She is portrayed as rational and straight-thinking as a counterbalance to Puddinghead's eccentricities. Applejack plays her in the Hearth's Warming Eve pageant.

Enterplay collectible card game Marks in Time expansion set card #21 C of Smart Cookie gives her the description "After helping to fuel the Fire of Friendship, Smart Cookie went on to revolutionize farming and irrigation systems throughout the budding nation of Equestria."

Quotes
"Found you!"

- Chancellor Puddinghead, The Journal of the Two Sisters

"This! Is! PEGASOPOLIS!"

- Commander Hurricane, Enterplay collectible card game Marks in Time card #6 C