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- Yield:Makes 4 sandwiches
- Active time: 30 minutes
- Total time:30 minutes
- For the Candied Bacon:
- 16 strips thick-cut bacon
- 1/4 cup packed dark brown sugar
- 3/4 teaspoon ground cinnamon
- 3/4 teaspoon ground ginger
- 1/2 teaspoon ground black pepper
- For the Tomato Jam:
- 3 tablespoons olive oil
- 1 1/2 pounds cherry tomatoes, halved
- 3 tablespoons packed dark brown sugar
- 3 medium cloves garlic, minced (about 1 tablespoon)
- 1 small shallot, minced (about 2 tablespoons)
- 2 tablespoons red wine vinegar
- 2 tablespoons Worcestershire sauce
- 1 teaspoon red pepper flakes
- Kosher salt and freshly ground black pepper
- For the Assembly:
- 8 slices (about 3/4-inch thick) brioche loaf or other soft loaf bread
- 2 tablespoons mayonnaise
- 8 thin slices cheddar cheese
- 4 teaspoons Dijon or spicy mustard
- 8 small iceberg lettuce leaves
For the Candied Bacon: Adjust oven racks to upper middle and lower middle positions and preheat oven to 400°F. Line 2 rimmed baking sheets with foil. Arrange 8 bacon strips in single layer on each sheet. Combine brown sugar, cinnamon, ginger, and pepper in small bowl. Rub sugar mixture all over both sides of bacon strips and bake until crisp, 16 to 18 minutes, alternating sheets’ positions and turning bacon strips with tongs halfway through baking. Transfer sheets to cooling racks and transfer bacon to large plate. When cool enough to handle, discard rendered fat and foil.
For the Tomato Jam: While bacon cooks, heat oil in large skillet over medium-high heat until shimmering. Add tomatoes, brown sugar, garlic, shallot, vinegar, Worcestershire, red pepper flakes, 1/2 teaspoon salt, and 1/2 teaspoon pepper, and cook, stirring until tomatoes are softened and lightly browned, about 15 minutes. Transfer to bowl and let cool to room temperature.
For the Assembly: Spread both sides of each bread slice with mayonnaise. Arrange bread on now-empty baking sheets and bake until browned, turning once halfway through cooking, about 6 minutes.
Transfer bread to cutting board. Spread 4 slices with mustard. Top remaining 4 slices with 1 slice cheese.
Spread mustard-spread slices with tomato jam, then top with 4 slices bacon, and lettuce. Press remaining 4 slices, cheese-side down, onto lettuce. Slice on the diagonal and serve.