Italian Mother-In-Law Dressing
['1/4 cup (1/2 stick) unsalted butter plus more for baking dish', '1/4 cup golden raisins', '3 cups low-sodium chicken broth, divided', '1 pound good-quality day-old country bread, torn into 1/2" pieces (about 10 cups)', '8 tablespoons olive oil, divided', '1 bunch red Swiss chard, center ribs and stems removed and cut into 1/2" pieces, leaves torn', '2 1/2 cups chopped yellow onions', '5 garlic cloves, chopped', '1/4 cup red wine vinegar', '1 tablespoon sugar', '1 cup pitted green olives, 3 coarsely chopped', '4 ounces pine nuts (about 1/2 cup), toasted', '1 tablespoon chopped fresh oregano', '1 tablespoon chopped fresh rosemary', '2 teaspoons kosher salt', '1/2 teaspoon crushed red pepper flakes', '2 large eggs']
Preheat oven to 250°F. Butter a 13x9x2" baking dish; set aside. Soak raisins in 1 cup broth in a small bowl for 30 minutes.
Scatter bread in a single layer on a rimmed baking sheet. Bake, stirring occasionally, until dried out, about 1 hour. Let cool and transfer to a very large bowl.
Heat 2 tablespoons oil in a large skillet over medium-high heat; add Swiss chard leaves and stir constantly until just wilted. Transfer to bowl with bread. Heat 2 tablespoons oil in same skillet; add stems and cook, stirring often, until crisp-tender, 3-5 minutes. Add to bowl.
Heat 4 tablespoons oil and 1/4 cup butter in same skillet; add onions and garlic. Stir often until just beginning to brown, about 10 minutes. Stir in vinegar and sugar; cook until vinegar is almost evaporated, about 5 minutes.
Add onion mixture to chard in bowl. Add raisins with broth, olives, and next 5 ingredients; gently fold into bread mixture until thoroughly combined. Drizzle in 1 cup broth and toss gently. Let cool completely.
Preheat oven to 350°F. Whisk remaining 1 cup broth and eggs in a small bowl. Gently fold into dressing until thoroughly combined. Transfer to prepared dish, cover with foil, and bake until an instant-read thermometer inserted into the center of dressing registers 160°F, about 40 minutes. DO AHEAD: Dressing can be made 1 day ahead. Uncover; let cool. Cover; chill.
Bake dressing, uncovered, until set and top is browned and crisp, 40-45 minutes longer (if chilled, add 10-15 minutes).
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