Recipe courtesy of Rick Massa

Heirloom Grilled Cheese Sandwich and Chunky Tomato Bacon Soup

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  • Level: Easy
  • Total: 20 min
  • Prep: 5 min
  • Cook: 15 min
  • Yield: 4 servings
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Grilled Cheese Sandwich:

1 stick unsalted butter, softened

1 tablespoon grated Parmigiano-Reggiano

1 tablespoon Dijon mustard, plus 4 tablespoons

8 slices Shephard's bread

8 ounces white Cheddar cheese, shredded

1 heirloom tomato, sliced into 3 (1/8-inch) slices

8 strips thick sliced apple wood smoked bacon, fried

Tomato Soup:

1 (28-ounce) can crushed tomatoes

2 tablespoons extra-virgin basil olive oil

3 tablespoons finely diced shallots

2 garlic cloves, finely diced

2 tablespoons finely chopped thyme leaves

2 tablespoons finely chopped basil leaves

3 strips thick sliced apple wood smoked bacon, fried and diced

3 ounce tomato paste

1/2 cup heavy cream

1 cup chicken broth


Sugar, to taste

1 tablespoon chiffonnade basil, for garnish


  1. To make the grilled cheese sandwich: In a small mixing bowl, combine butter, Parmigiano-Reggiano, and 1 tablespoon Dijon mustard. Spread a liberal amount of butter mixture on 2 slices of bread. Flip over slices and spread some Dijon mustard on other sides. Place Cheddar cheese on the Dijon side of both slices. Place bacon on top of cheese on 1 slice and sliced tomatoes on top of cheese on other slice. Combine both sides together and place in a medium skillet over medium heat. Cook until golden brown and crusty. Flip sandwich and place a weighted cast iron pan on top. Cook until golden brown and cheese has melted. Remove from skillet and serve immediately with tomato soup.
  2. To make the soup: Puree the crushed tomatoes and set aside. In a heavy stainless steel pot, heat basil olive oil. Add shallots and cook until soft. Add garlic, thyme, chopped basil, bacon, and tomato paste and continue to cook, stirring with a wooden spoon. Add tomato puree, cream, chicken broth, and salt and sugar, to taste. Bring to a simmer. Pour soup into bowls and garnish with chiffonnade basil. Serve immediately with grilled cheese sandwich.