Preheat oven to 350 degrees. Tear bread into pieces; pulse in a food processor to make fine crumbs (or use plain breadcrumbs) set aside.P

Cook the Onions: Pulse onion in food processor until finely chopped (or do so by hand). Heat 2 tablespoons olive oil in a large skillet over medium-high. Add onion and 1 teaspoon kosher salt to skillet; cook, stirring occasionally, until onion is softened, about 8 minutes. Stir in Worcestershire sauce, broth, and 1/4 cup ketchup. Remove from heat; let cool completely.

Prep the Meat and Glaze: In a small bowl, stir together 1/2 cup ketchup and brown sugar for glaze; set aside. In a large bowl, combine onions with ground chuck, 1 egg, 1/2 cup reserved breadcrumbs, 2 teaspoons salt, and 1/2 teaspoon freshly ground pepper. Mix with your hands until well combined. Gently fold in cheddar.

Bake and Let Cool: On a rimmed baking sheet, form meat mixture into a loaf that's 10 inches long, 4 inches wide, and 2 inches high, packing firmly to prevent cracking. Coat top and sides with 1/2 of glaze, then top with bacon, overlapping slices slightly. Brush remaining glaze over bacon. Bake until top is caramelized and a thermometer inserted into thickest part registers 165 degrees, 55 to 65 minutes. (If top is browning too quickly, tent with foil.) Let cool at least 25 minutes.