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1
Prepare the bacon: Place rack in the center of the oven and preheat to 400 F. Line a large rimmed baking sheet with foil.
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2
Arrange bacon slices in a single layer on a flat ovenproof rack, then set the rack atop the prepared baking sheet.
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3
Put it into the oven.
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4
Bake bacon for 10-15 minutes, until crispy.
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5
Once cooked, carefully remove the pan from the oven, set bacon between two paper towels and pat dry.
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6
Cut each slice in half and set aside.
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7
Preheat a cast-iron skillet to medium low.
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8
Melt half of the butter in the skillet.
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9
In a small bowl, gently smash and stir the raspberries, jam, and chipotle powder with the back of a spoon.
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10
The mixture should remain fairly chunky.
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11
Assemble the sandwiches (makes 2 sandwiches): For each sandwich, layer one slice of bread with a quarter of the cheddar, a quarter of the berries, four half-slices of bacon (2 full slices), an additional quarter of the berries, then one additional quarter of the cheese.
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12
Carefully set one loaded bread slice down in the buttered skillet.
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13
Place one remaining bread slice on top of the stack, then spread half of the remaining butter on the top of the bread.
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14
Cook slowly until the bread is golden and the cheese is hot and melted, flipping once.
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15
This will take about 4 to 5 minutes per side.
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16
(I find it helps to place a lid or another heavy skillet directly over the pan.)
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17
Repeat cooking the second sandwich.
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18
Slice and serve immediately.
