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Preheat oven to 400°F. Trim fat from chops. Place chops in a large self-sealing plastic bag set in a shallow dish. For marinade, in a small bowl whisk together bourbon, maple syrup, soy sauce, tomato paste, lime juice, and serrano pepper. Pour marinade over chops in bag, turning bag to coat evenly. Marinate in the refrigerator while preparing squash hash, turning bag occasionally.
For squash hash, in a large bowl combine the squash, sweet pepper, leeks, 3 tablespoons of the olive oil, the jalapeño pepper, salt, and black pepper. Spread the squash mixture in a 15x10x1-inch baking pan. Roast, uncovered, for 25 to 30 minutes or until vegetables are tender and browned, stirring twice.
Meanwhile, drain chops, reserving marinade. In a very large skillet heat the remaining 1 tablespoon oil over medium-high heat. Add chops to hot oil; cook for 6 to 8 minutes or until browned, turning once. Place chops in a shallow baking pan. Place chops in oven on the rack below squash. Roast for 10 to 12 minutes or until an instant-read thermometer inserted in chops registers 145°F. Let chops stand for 5 minutes before serving.
For sauce, place the marinade in a small saucepan. Bring to boiling; reduce heat. Simmer, uncovered, about 5 minutes or until reduced by half (1/3 cup). Transfer chops and squash mixture to serving plates. Drizzle chops with sauce.