For the roulade: Preheat the oven to 375 degrees F. Spread the pine nuts onto a small sheet tray and place in the oven to toast, 5 to 7 minutes.
Set up a large pot of well-salted boiling water. Set up a large bowl of well-salted ice water. Blanch the broccoli rabe for 1 minute until bright green and tender, but still crisp. Remove from the boiling water and plunge immediately into the ice bath. Once cool, remove from the ice bath and use your hands to squeeze out excess water. Finely chop the broccoli rabe and add to a large bowl with the sausage, pine nuts, parmesan, breadcrumbs, egg and crushed red pepper. Sprinkle with salt.
Heat a small saute pan over medium-high heat with a little olive oil. Take a small amount of filling and cook a small tester patty to test for seasoning. Adjust the seasoning on the remaining raw mixture if needed.
Trim any excess fat from the pork chops. Cut the pork lengthwise to butterfly, then pound to an even thickness of 1/4 to 1/2 inch. Lay a large piece of caul fat out on a large, flat work surface. Place 4 slices of prosciutto over the caul fat, followed by the pounded pork loin on top of the prosciutto. Set half the broccoli rabe and sausage filling on top of the pork loin and shape into a thin log. Wrap the prosciutto and pork loin around the filling and roll into a tight log. Wrap the caul fat around the stuffed pork, cutting off any excess from the ends, making sure the caul fat is in one even layer around the pork. Tie with butcher’s twine to secure and trim any excess string. Repeat with the remaining pork and filling.
Heat a large saute pan with olive oil over high heat. Sear the roulades, turning on all sides, until golden brown, 5 to 7 minutes. Transfer the pork to a sheet tray and place into the oven and reserve the pan that the pork was cooked in. Roast the pork at 375 degrees F for 15 to 20 minutes, or until an instant read thermometer registers 150 degrees F. Let rest for 5 to 10 minutes, then remove the string.
Place the pan that the pork was cooked in back onto medium-high heat and drain off any remaining fat. Add the shallot and cook for 2 minutes until tender. Deglaze the pan with the white wine and stir, making sure to scrape the bits from the bottom of the pan. Cook until almost all of the liquid has reduced, then add half the chicken stock. Continue to cook until the liquid has reduced by half, then add the remaining chicken stock. Cook until slightly reduced then remove from heat.
Slice the pork into 1/2-inch-thick rounds. Plate alongside the mashed potatoes and a drizzle of sauce over the pork.
Mustard Mashed Potatoes:
Place the potatoes in a large saucepan. Add cold water to cover the potatoes by 1 to 2 inches and generously season with kosher salt. Bring the pot of water to a boil and cook until the potatoes are fork-tender, 20 to 25 minutes.
Meanwhile, heat the heavy cream in a small saucepan over medium-low heat. Drain the potatoes and add back to the large saucepan. Using an electric hand mixer, mix the potatoes and gradually add the butter and warmed heavy cream, alternating, until the potatoes reach a creamy and silky consistency. You may not need to use all the heavy cream. Add the whole-grain mustard, Dijon mustard and kosher salt to taste and mix thoroughly to combine. Makes 4 servings
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