Savory Bread Pudding with Tomato Bacon Jam

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Savory Bread Pudding:

Unsalted butter, for greasing

1 tablespoon extra-virgin olive oil 

4 slices bacon 

2 cloves garlic, minced 

1 bell pepper, chopped 

1 carrot, chopped

1 rib celery, chopped 

1 onion, chopped

4 ounces mushrooms, sliced 

1 tablespoon garlic powder 

1 tablespoon onion powder 

1/2 teaspoon crushed red pepper flakes 

Kosher salt and ground black pepper 

2 tablespoons chopped basil 

2 tablespoons chopped parsley 

1 tablespoon chopped rosemary 

1 tablespoon chopped sage 

1 tablespoon chopped thyme 

6 large eggs 

Splash milk 

1 loaf brioche bread, cubed

Grated Parmigiano-Reggiano, for sprinkling

Tomato Bacon Jam:

Extra-virgin olive oil, for drizzling

4 tomatoes, chopped 

2 slices bacon, cubed 

1 clove garlic, minced

1 shallot, chopped

1/2 cup frozen black cherries 

Kosher salt and ground black pepper

Bloody Mary:

Ice

12 ounces vodka

Hot sauce

Worcestershire sauce

Bloody Mary mix, as needed

Celery stalks, olives, lemon wedges, etc, for garnish, as desired