2 cups dry red wine
2 tablespoons balsamic vinegar
5 cloves garlic, minced
2 teaspoons ground cumin
1/2 teaspoon ground cinnamon
1 teaspoon salt
1/2 teaspoon black pepper
1/4 teaspoon crushed red pepper flakes
2 pounds beef flank steak
For marinade, in a medium bowl combine wine, vinegar, garlic, cumin, cinnamon, salt, pepper, and crushed red pepper. Set aside.
Score the flank steak to allow the marinade to penetrate. Place the meat in a resealable plastic bag set in a shallow dish. Add marinade. Seal the bag and marinate in the refrigerator for 4 to 8 hours, turning occasionally.
Place beef on the rack of an uncovered grill directly over medium coals. Grill 17 to 21 minutes or until an instant-read thermometer inserted in center registers 145 degrees for medium-rare doneness or 160 degrees for medium doneness. (Or preheat gas grill. Reduce heat to medium. Place meat on rack over heat. Cover; grill as above.) Thinly slice meat against grain. Season to taste with salt and pepper.
As prepared, each serving contains 290 calories, 8g total fat, 50mg cholesterol, 480mg sodium, 4g total carbohydrate and 33g protein.