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Step 1
In a large heavy pot or Dutch oven, cook the bacon until browned and crisp. Drain on a paper towel drained plate. Remove all but 1 tablespoon of the bacon grease from the pot. Add in the onion and cook until softened, about 8 minutes. Stir in the water, maple syrup, vinegar, brown sugar and Dijon mustard. Bring to a boil, then reduce the heat to a simmer. Add the bacon back in. Cook, stirring occasionally, until thickened, 1-2 hours. If it gets too thick, add in a little more water.
Step 2
Transfer the mixture to a food processor. Pulse a few times to break it down into a spreadable consistency.
Step 3
Butter the outsides of each of the pieces of bread. Place a slice of Cheddar cheese on the unbuttered side of 4 pieces of the bread. Spread some of the bacon jam on top of the cheese. Divide the Brie between the sandwiches and layer on top of the jam, followed by a slice of American cheese. Place the remaining bread on top of the cheese, buttered side out.
Step 4
Heat a griddle over medium-low heat. Cook the sandwiches until golden brown and the cheese has melted.