Fill a large container with water. Add the salt, sugar, fennel seeds, garlic, fennel tops and onion. Add the pork chops and allow to sit in the brine for 2 hours.
Preheat the oven to 400 degrees F.
Arrange the delicata rounds and butternut chunks on separate sheet trays. Drizzle with the olive oil and sprinkle with salt. Roast until tender, 25 to 30 minutes.
Heat the apple cider in a medium saucepan over medium heat. Cook to reduce for 20 minutes. Add 2 cups chicken stock and continue to reduce for 20 minutes.
Preheat a large cast-iron pan with some olive oil on medium-high heat. Remove the pork from the brine and pat dry. Sprinkle with the fennel pollen and salt. Place in the pan and sear until golden brown and it reaches an internal temperature of 145 degrees F, 4 to 5 minutes per side.
Coat a high-sided saute pan with olive oil. Add the shallot and some salt and sweat over medium-high heat until translucent, about 5 minutes. Add the apples and cook until they start to soften, 3 to 4 minutes. Add the warmed apple cider and remaining cup chicken stock and season with salt. Cook until slightly reduced, a few minutes, then add the golden raisins. Continue to reduce the sauce, adding a bit more chicken stock every so often, until the sauce is slightly thickened, 10 minutes. Finish the sauce with the butter.
To a separate saute pan, add the pancetta and turn on the heat to medium. Slowly cook the pancetta, stirring occasionally, until the fat has rendered and the pancetta is crispy. Add the crushed red pepper flakes. Add the sliced fennel and kale and season with salt. Stir to combine, then add the apple cider vinegar. Add the roasted butternut squash and gently toss to combine. Season to taste with salt and a drizzle of olive oil.
To plate: Plate two slices of roasted delicata squash. Top with the sauteed kale and butternut squash. Top with a pork chop, then another slice of delicata squash. Spoon the sauce over the top and garnish with the pepitas and fennel pollen. Repeat to make 3 more servings.
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