Artist’s description from DA:

I REALLY liked how these guys came out so I decided to go ahead and upload it here. This is straight from the Headcanon book, featuring my versions of the original founders of Equestria. I think of all of them here, Pansy’s probably my favorite. :3 But anyway, a small summary for these puppies:

Clover the Clever-

Clover in my headcanon is the direct servant (and somewhat bodyguard) to the Princess Platinum, in addition to being the apprentice of Starswirl the Bearded. Despite her lower rank and hardship, Clover is devoted to both her mentor and her princess. She goes on to become one of the most well known unicorn mages in all of Equestria. As a small note, she’s actually an ancestor of Twilight Sparkle, hence why she kinda looks like her.

Princess Platinum-

Platinum was very well known for her beauty and her treatment toward those of lower-ranking than her. Unlike her father, Platinum was more willing to accept the blending between the unicorns, pegasi, and earth ponies, as well as better listen to the plights of her subjects. As such, she was a more popular ruler than the likes of her father. It is often rumored that she and Clover were secret lovers (this was back when same-sex couples weren’t as widely accepted) but not much could be used to confirm this. Platinum is a distant ancestor of Rarity’s.

Commander Hurricane-

A gruff, strong, and impatient pegasus, Hurricane obtained his place of power mostly through being completely bull-headed and stubborn as a jackass. That’s not to say he wasn’t a good leader, but he certainly wasn’t the best. So deep was his racism against other breeds that he outright refused the aid from the other kingdoms when his own kingdom needed it the most. It’s his racism and overbearing pride that eventually forces him to step down as leader. He has sired several illegitimate foals from many mares, so he may or may not be an ancestor of sorts to Rainbow Dash.

Lieutenant Pansy-

While Pansy allowed the use of male pronouns (different gender identity wasn’t widely accepted at this time either), they’re actually non-binary. The use of male pronouns was mostly to protect themselves from the violence that often came with not conforming to what was considered “normal”, especially among the pegasi back then. Pansy isn’t their real name, but it’s the name they were often called due to their very timid and skittish nature. However, one of the defining traits to Pansy is the fact that, despite being scared most of the time, they never hesitated to do what they thought was right. Pansy, in short, was a brave pegasus. Possibly the anscestor of Fluttershy.

Smart Cookie-

Most-definitely an anscestor to Applejack, she was quite possibly the origin of the Apple clan. Smart Cookie is called such because she’s exactly that: intelligent, very resourceful, and reliable. It’s no wonder why she was Chancellor Puddinghead’s secretary. She and Puddinghead aren’t related however they considered each other kin, their relationship often likened to that of a father and daughter’s.

Paddock (Puddinghead)-

While Paddock is his real name, the Earth pony leader of that time was often referred to as Puddinghead. So much so that records of his real name are very rare; why that is, no one really knows. Of the leaders of that time, Puddinghead was possibly the most progressive; he treated anyone equally despite their breed, and was far more willing to listen to ideas and concepts that was probably considered ahead of his time. A beloved leader of the Earth Pony tribe. He and Smart Cookie aren’t related but they do treat each other like father and daughter, and as such he was possibly an “honorary member” of Smart Cookie’s clan, just as much as she was a part of his own. Possible ancestor of Pinkie Pie–