Combine olives, rosemary, garlic, crushed red pepper, salt, and pepper in processor. Blend until olives and garlic are chopped finely. With machine running, add 4 tablespoons oil through feed tube and blend until coarse paste forms. (Olivada can be made 1 day ahead.
Transfer to small bowl, cover, and refrigerate.)
Position rack in bottom third of oven and preheat to 425°F. Starting at neck end of chicken, carefully slide hand under skin, loosening skin over breast, thighs, and top of drumsticks.
Spread olive paste as evenly as possible over meat under loosened skin. Rub outside of chicken with remaining 1 tablespoon oil. Fold wing tips under; tie legs together loosely to hold shape.
Place chicken on rack set in roasting pan.
Roast chicken until skin is golden brown and thermometer inserted into thickest part of thigh registers 180°F, about 1 hour 20 minutes. Using carving fork, tilt chicken to empty juices from cavity into pan.
Place chicken on platter; tent loosely with foil.
Pour pan juices into 2-cup glass measuring cup; spoon off fat that rises to top.
Add wine and enough broth to juices to measure 1 1/3 cups.
Pour liquid back into same roasting pan. Set pan over 2 burners and boil until sauce thickens and reduces to 3/4 cup, scraping up browned bits, about 5 minutes. Season sauce with salt and pepper; pour into gravy boat.
