Chef Linda's taking grilled cheese sandwiches to the max!
Preheat oven to 425°F.
Place peeled and halved squash on a sheet pan. Rub with olive oil and season with salt and pepper. Roast for 30 minutes, or until tender and beginning to brown. Set aside to slightly cool. Once cooled, slice thin.
Heat a grill pan with butter.
Butter one side of all 8 slices of bread. Place 4 slices of bread (butter side down) onto grill pan. Build each sandwich by layering on the Brie, squash slices, onion slices, and kale. Top each sandwich with bread (butter side up).
Cook sandwiches until browned. Carefully turn the sandwiches and press down slightly, cooking until bottom side is browned.