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The love story of Bright Mac and Pear Butter is one known to many residents of Ponyville, with the intensity of their love for one another breaking traditions and ending a generations-long feud between their families. The unfortunate, miserable, end that came for the two lovers is much less widely known. Pear Butter, now Buttercup, was anemic and diabetic. She was known as a frail, delicate thing, unsuited to a life of hard labor. Each of her pregnancies was a waking hell, marked by fainting spells and nightmarish labors that lasted many hours. None of the children were planned, and Bright Mac made Buttercup promise him that after the birth of their third child, they would both seek out medical intervention to ensure that Buttercup bore no more children. This promise, however, came too late.

Buttercup labored for nearly two days, her lastborn refusing to come. When the foal finally came, poor Buttercup was a hollow shell of her former self. Her own health problems compounded with the difficult, traumatic labor, and a nervous young physician who used unclean tools on the mare, led to a steady but swift decline. Buttercup lived for a week after the birth of Apple Bloom before infection and exhaustion finally took her.

Bright Mac was never the same. He threw himself into his work, hoping that if he saved up enough money, he would be able to pay for a nanny and wet-nurse to care for his children without their mother. Each season without Buttercup was spent toiling in the fields, harvesting, and peddling goods. Bright Mac was destroying himself with his work. He was reckless, working long into the night when timberwolves were about, going out into storms to deliver goods, and spending his free hours wandering the fields, alone in his grief.

On a horrible night in August, when summer storms threatened to blow the entire orchard down, Bright Mac ventured out alone to secure the trees while his mother and foals slept. In his attempts to secure the trees, a branch fell, pinning him underneath a tree limb and puncturing his lung. He lay there all through the night, calling out for his wife, for his family, only for his cries to be drowned out by the storm. Big Macintosh was the one to find him, and he has never been the same since.