Name: Radicchio Jam Rigatoni
Yield: 4 servings
Ingredients: Freshly ground pepper; 5 garlic cloves, finely chopped; Kosher salt; 4 Tbsp. unsalted butter; 2 Tbsp. sugar; 4 oz. guanciale (salt-cured pork jowl) or pancetta (Italian bacon), cut into ½" pieces; 2 large sweet onions (such as Vidalia; about 1 lb.), quartered through root ends, thinly sliced crosswise; Extra-virgin olive oil (for pan and drizzling); 1 small head of radicchio (about 1 lb.), quartered through root end, cored, cut into 1" pieces, divided; 2 small sprigs thyme, leaves picked; ¼ cup red wine vinegar; 12 oz. rigatoni or other short pasta; 2 oz. Parmesan, finely grated (about 1½ cups); Lemon wedges (for serving)

Instructions

Cook 4 oz. guanciale (salt-cured pork jowl) or pancetta (Italian bacon), cut into ½" pieces, in a dry medium Dutch oven or other heavy pot over medium-high heat, stirring occasionally, until light golden brown and starting to crisp, about 5 minutes (don’t let pieces get too crunchy). Using a slotted spoon, transfer to a small plate, leaving fat behind.
Add 2 large sweet onions (such as Vidalia; about 1 lb.), quartered through root ends, thinly sliced crosswise, and a small pinch of kosher salt to same pot (if it looks dry, add up to 2 Tbsp. extra-virgin olive oil) and cook, stirring often, until deep golden brown, 15–18 minutes.
Set aside a small handful (about ½ cup; eyeballing is fine) of 1 small head of radicchio (about 1 lb.), quartered through root end, cored, cut into 1" pieces for serving and add remaining radicchio to pot. Add 5 garlic cloves, finely chopped, and 2 small sprigs thyme, leaves picked, and cook, stirring often, until radicchio is softened and wilted, 5–8 minutes.
Reduce heat to medium and add ¼ cup red wine vinegar, 2 Tbsp. sugar, and ½ cup water; cook, stirring occasionally, until liquid is syrupy and onions are very tender, 5–8 minutes.