Make the roasted garlic. Preheat over to 400 degrees. Cut the root end off the head of garlic, exposing the bottom of the garlic cloves. Drizzle exposed cloves with 1 tablespoon of the olive oil and insert 4-5 rosemary needles into the garlic. Place the remainder of rosemary sprig on top of the garlic. Season with salt and pepper to taste.
Wrap the garlic in aluminum foil, then put in oven. Roast until garlic is brown and getting very soft, 30-45 minutes. Set aside to cool when done roasting. Keep the oven on.
When the garlic has cooled, squeeze the roasted garlic out of the skin into a small bowl. Whip the garlic with a spoon to achieve a consistent texture.
As the garlic roasts, lightly coat the steak with olive oil and season with salt and pepper to taste. Let stand for about 15 minutes at room temperature.
Coat an oven proof skillet with olive oil or canola spray, and place on the stove top on medium high heat. Brown the steak on the stove top, about 2 minutes per side.
Place skillet in the oven and roast steaks to desired doneness, about 7 to 9 minutes for medium rare. Note the steaks will continue to cook while you make the sauce, so take care not to overcook this lean cut.
When the steaks are done to your liking, place on a platter and tent with aluminum foil. Keep the juices and fat in the pan. Melt butter in pan on medium heat. Add the roasted garlic and cook for 2-3 minutes. Add the wine and vinegar, cook for another two minutes or so. Uncover the steak, stir extra juice from the platter into the sauce.
Pour the sauce into a serving bowl. Stir in the truffle oil if you are fortunate enough to have it.
Cut the steak into slices about 1/2 inch thick. Plate several slices of steak, topped with some sauce. Repeat for the other servings. Pass extra sauce at the table and enjoy!