PreparationFor pork: Mix first 8 ingredients in a large bowl. Add pork and toss to coat. Cover and chill, tossing occasionally, at least 8 hours or overnight. Heat 2 tablespoons oil in a large heavy pot over medium-high heat. Working in batches, brown pork on all sides, lowering heat if meat begins to scorch, about 5 minutes per batch. Using tongs, transfer pork to a medium bowl. Add remaining 1 tablespoon oil and onions to pot; sauté until slightly softened and golden brown, about 5 minutes. Add wine; cook, scraping up browned bits, until reduced by half, about 2 minutes. Add broth; return pork to pot. Reduce heat to low, cover pot, and simmer, stirring occasionally, until pork is tender, about 2 hours. Reserve 3/4 cup braising liquid for radicchio. Set pork in remaining liquid aside. DO AHEAD: Can be made 2 days ahead. Chill pork and reserved 3/4 cup braising liquid separately (uncovered) until cold, then cover and keep chilled. Rewarm before serving. For radicchio and salad: Heat 1 tablespoon oil in a large skillet over medium-high heat. Working in batches, add radicchio and sauté on each cut side, adding more oil to pan between batches if needed, until browned, 2-3 minutes per side; transfer radicchio to a plate. Place all cooked radicchio back in skillet and add reserved pork-braising liquid. Cover and cook until crisp-tender, about 3 minutes. Add 2 tablespoons vinegar; bring to a simmer and cook, uncovered, until juices have thickened, about 1 minute. Season to taste with salt and pepper. Toss arugula, remaining 3 tablespoons oil, and lemon juice in a large bowl. Season to taste with salt and pepper. Divide pork with juices among plates. Arrange radicchio alongside. Divide arugula salad among plates. Drizzle radicchio with oil and a small amount of vinegar.
PreparationFor pork: Mix first 8 ingredients in a large bowl. Add pork and toss to coat. Cover and chill, tossing occasionally, at least 8 hours or overnight. Heat 2 tablespoons oil in a large heavy pot over medium-high heat. Working in batches, brown pork on all sides, lowering heat if meat begins to scorch, about 5 minutes per batch. Using tongs, transfer pork to a medium bowl. Add remaining 1 tablespoon oil and onions to pot; sauté until slightly softened and golden brown, about 5 minutes. Add wine; cook, scraping up browned bits, until reduced by half, about 2 minutes. Add broth; return pork to pot. Reduce heat to low, cover pot, and simmer, stirring occasionally, until pork is tender, about 2 hours. Reserve 3/4 cup braising liquid for radicchio. Set pork in remaining liquid aside. DO AHEAD: Can be made 2 days ahead. Chill pork and reserved 3/4 cup braising liquid separately (uncovered) until cold, then cover and keep chilled. Rewarm before serving. For radicchio and salad: Heat 1 tablespoon oil in a large skillet over medium-high heat. Working in batches, add radicchio and sauté on each cut side, adding more oil to pan between batches if needed, until browned, 2-3 minutes per side; transfer radicchio to a plate. Place all cooked radicchio back in skillet and add reserved pork-braising liquid. Cover and cook until crisp-tender, about 3 minutes. Add 2 tablespoons vinegar; bring to a simmer and cook, uncovered, until juices have thickened, about 1 minute. Season to taste with salt and pepper. Toss arugula, remaining 3 tablespoons oil, and lemon juice in a large bowl. Season to taste with salt and pepper. Divide pork with juices among plates. Arrange radicchio alongside. Divide arugula salad among plates. Drizzle radicchio with oil and a small amount of vinegar.