Yield: 2 sandwiches.
3 tablespoons mayonnaise
1 teaspoon light brown sugar
1 teaspoon apple cider vinegar
2 slices fresh pineapple
2 to 3 tablespoons unsalted butter, divided, at room temperature
4 slices fresh sourdough bread
4 slices deli ham
8 slices thick-cut bacon, cooked until crispy
4 slices sharp Cheddar cheese
In a small bowl, whisk together mayonnaise, brown sugar, and vinegar. Set aside.
Heat a cast-iron skillet over medium-high heat for 2 minutes. Place pineapple slices in skillet and reduce heat to medium. Cook for 1 to 2 minutes or until pineapple is lightly charred. Flip pineapple and heat the other side for 1 minute. Remove from skillet.
Melt 1 tablespoon of butter in large skillet over medium heat.
While skillet is heating, spread mayonnaise mixture on all four slices of bread. Layer 2 slices of Cheddar, a slice of pineapple, 4 bacon slices, and 2 ham slices on 2 of the sourdough slices; top with remaining bread.
Place sandwiches in hot skillet. Cook for 3 to 4 minutes, until bottoms of sandwiches are golden brown. Spread remaining butter on top bread slice and flip sandwich over. Cook until golden, 2 to 3 minutes. Remove sandwiches from skillet and cut in half. Serve hot.