8 slices thick-cut smoked bacon, cut in half crosswise
2 tablespoons maple syrup
Brioche buns, cut into 16 (1 ½-inch) squares
2 tablespoons unsalted butter, melted
1 pound 80/20 ground beef
Kosher salt and freshly cracked black pepper, for seasoning
4 slices extra-sharp white cheddar, cut into 16 squares
16 dill pickle round slices
8 cherry tomatoes, cut in half crosswise
16 (5-inch) bamboo skewers
Directions
To make the burger sauce, whisk together the mayonnaise, ketchup, Worcestershire sauce, smoked paprika, and garlic powder in a small bowl until smooth.
Cover and refrigerate until ready to serve.
Preheat the oven to 375 F.
Line a baking sheet with foil and parchment paper and fit it with a rack.
Lay the bacon pieces evenly over the rack.
Brush the maple syrup onto the bacon.
Bake for about 20 minutes until caramelized and crisp, flipping the bacon once.
Remove the bacon from the oven and transfer it to a paper towel-lined plate. Set aside.
Toss the brioche with the melted butter.
Line a separate baking sheet with parchment and arrange the buttered brioche in a single layer.
Bake for 5 minutes until golden brown and crisp on the outside. Remove from the oven and arrange in rows on a cutting board.
Form the beef into 16 patties.
Preheat a large, heavy skillet over medium-high heat.
Place the patties in the skillet and season with the salt and pepper.
Press down gently to sear and cook for 2 minutes on the first side.
Flip the patties and repeat with the pressing and seasoning, cooking for another 2 minutes.
Place a cheese square on the top of each patty.
Cover the skillet with a lid for 30 seconds to melt the cheese.
To assemble the skewers, place a patty on top of a brioche toast.
Fold a bacon strip to fit on top of the cheese, then follow with a pickle slice and tomato half, facing cut-side-down.
Drive a bamboo skewer straight down through the center of the stack to the bottom of the brioche.
Repeat with the remaining skewers.
Serve the cheeseburger skewers on a board or platter with small bowls of the burger sauce for dipping.