Spicy Tomato and Cheddar Soup

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4 tomatoes, halved

2 tablespoons olive oil 

2 cloves garlic, thinly sliced 

1 small red onion, chopped 

2 teaspoons fresh oregano leaves, chopped 

2 cups chicken broth 

1 teaspoon hot sauce

One 28-ounce can diced fire-roasted tomatoes 

Kosher salt and freshly ground black pepper 

Kosher salt and freshly ground black pepper

2 cups grated sharp Cheddar

Croutons, recipe follows

Croutons:

2 cups cubed day-old French bread

2 tablespoons olive oil

Kosher salt and freshly ground black pepper