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Pipsqueak is an earth pony, originally from Trottingham, come to Ponyville for reasons unknown. Often acts like a pirate, for reasons known only to him. He currently attends classes at Cheerilee's school.
His crew just got a lot larger, with the introduction of the Cake Twins, Smarty Pants, and Jim. Together, they pilage Ponyville for all of its treasure! Yarrrr