1. Preheat oven to 425 degree F.
2. Toss tomatoes with 1 tablespoon oil in a shallow heavy baking pan; spread out, leaving room in center for beef. Season with salt and pepper.
3. Rinse and pat beef dry. Wrap with bacon, slightly overlapping slices and tucking ends under beef.
4. Roast, turning tomatoes occasionally, until an instant-read thermometer inserted in center of beef registers 122 degree F for medium-rare and tomatoes are golden brown, 30 to 35 minutes.
5. Transfer beef in pan to rack; let stand 15 minutes before carving into 1/3-inch-thick slices, discarding string. Meanwhile, toss arugula with cheese, vinegar, and remaining 1 tablespoon oil. Salt and pepper to taste.
6. Place tomatoes on opposite sides of a large serving platter, gently combine with salad and sprinkle with cheese. Arrange beef slices in center of platter; season with pepper. Makes 6 servings.