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Prepare a grill for high heat. Brush both sides of baguette slices with 4 tablespoons of olive oil. Grill bread, turning once, until crisp and lightly charred, 20 to 30 seconds per side. Transfer to a plate.
Place brie in a cast-iron skillet. Using a sharp knife, score the top of the rind in a crisscross pattern. Stuff half of the garlic into slits; sprinkle the remaining garlic over top. Drizzle brie with wine and the remaining 1 tablespoon of olive oil. Top with thyme and season with salt and pepper.
Place cast-iron skillet on grill rack and close lid. Grill until cheese is warmed through and feels melted and gooey in the middle, 8 to 10 minutes. Serve brie in the skillet with toast alongside.
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