Bacon-wrapped meatloaf is a wonderful thing and it's only more wonderful when the beefy meatloaf is amped up with cheddar cheese. Try slices on buns with iceberg lettuce and Russian Dressing.
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.