Pour 2 teaspoons oil in a medium pot and heat over medium heat. Saute onion 10 minutes. Stir in cranberries, wine, oregano, chile, and garlic and cook 10 minutes or until the liquid absorbs.
Preheat oven to 375 degrees F.
Add 1/2 teaspoons salt, cumin, and chile powder to a bowl. Slice turkey lengthwise, cutting to, but not through the other side. Open halves flat and cut again, to, but not through the other side. Lay plastic wrap over turkey and flatten to 1/2 inch thickness using a meat mallet or heavy rolling pin. Season turkey with spice mixture and spoon 1/3 cup cranberry mixture on each tenderloin. Roll tenderloins up and secure with toothpicks. Season the turkey with salt and pepper.
Pour 2 teaspoons oil in a frying pan and heat over medium-high heat. Cook turkey in pan 3 minutes, browning on all sides. Bake at 375 degrees F for 25 minutes or until a meat thermometer reads at least 165 degrees F. Take turkey out of oven and let rest 10 minutes before slicing. Garnish with oregano.