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Put your brisket in a smoker and pour the bourbon and maple syrup over it. The liquid should mostly cover the meat. Set it to cook on low for 8 hours.
After 8 hours, your brisket should be super tender and fall apart easily. Take it out and shred it with two forks. Save some of the cooking liquid.
Heat up a big skillet over medium heat. Butter one side of each slice of bread.
Put one slice of bread in the skillet, butter-side down. Pile on some cheddar cheese, a good amount of that amazing shredded brisket, more cheese, then top with another slice of bread, butter-side up.
Cook the sandwich for about 3-4 minutes until the bottom is golden brown, then carefully flip it over. Cook another 3-4 minutes until the other side is golden and all the cheese has melted.
While you’re making the sandwiches, heat up your waffles however the package says.
Take one hot waffle and put a whole grilled cheese sandwich on top. Then put another waffle on top of that. Press down gently.
Cut each wafflewich in half and serve immediately while everything is hot.