01 -
In a medium mixing bowl, whisk together ketchup, Jack Daniels, brown sugar, Worcestershire sauce, honey, and red pepper flakes until consistent. Refrigerate and seal if possible.
02 -
Set your smoker to 225°F (107°C) and use apple wood chunks for smoking.
03 -
In a large mixing bowl, combine ground chuck, milk, grated red onion, Jack Daniels, Worcestershire sauce, crumbled saltine crackers, cayenne, garlic powder, beaten eggs, and 2/3 of the prepared Jack Daniels glaze. Mix until just combined, taking care to not overwork the meat.
04 -
On a medium grill pan with drainage holes, shape half of the meat mixture into a solid base. Create a dent in the center to add folded cheese slices. Cover with the remaining meat mixture, shaping it to ensure there are no gaps or holes.
05 -
Brush 2/3 of the Jack Daniels glaze over the shaped meatloaf for an even coating.
06 -
Place the meatloaf in the smoker and cook for 4 hours, or until the internal temperature reaches 165°F (74°C). Brush with another layer of glaze halfway through cooking (at 2 hours).
07 -
Let the meatloaf rest under aluminum foil at room temperature for 8-10 minutes. Slice into 1/2 to 1-inch thick portions and serve.