- 3 tablespoons fruity olive oil, divided
- 4 garlic cloves; 2 thinly sliced, 2 pressed
- 1/4 teaspoon dried crushed red pepper
- 1 bay leaf, preferably fresh, broken in half
- 1/3 cup finely chopped shallots
- 1/4 cup finely chopped fresh Italian parsley
- 2 tablespoons finely chopped pitted Kalamata olives
- 2 tablespoons red wine vinegar
- 2 14- to 16-ounce 2-inch-thick grass-fed New York strip steaks
- 1 teaspoon coarse kosher salt
- 1/4 teaspoon cayenne pepper
Heat 2 tablespoons oil in heavy medium skillet over medium heat. Add sliced garlic, red pepper, and bay leaf. Stir until fragrant, about 1 minute. Add shallots and sauté until just translucent, about 2 minutes. Remove from heat; stir in parsley, olives, and vinegar. Add 1 tablespoon water. Add more water by teaspoonfuls to thin as needed. Season chimichurri with salt and pepper. DO AHEAD Can be made 2 hours ahead. Let stand at room temperature.
Rub steaks with 1 tablespoon oil and pressed garlic. Sprinkle both sides of each steak with 1/2 teaspoon paprika, 1/4 teaspoon coarse salt, cayenne, and generous amount of black pepper. Let stand at room temperature 30 minutes or up to 2 hours.
Preheat oven to 400°F. Brush heavy very large ovenproof skillet (preferably cast-iron) with oil. Heat over high heat until almost smoking. Add steaks. Cook until browned, about 5 minutes. Turn steaks and transfer skillet to oven. Roast until instant-read thermometer inserted horizontally into steaks registers 110°F to 115°F for rare, about 10 minutes.
Let steaks rest 5 minutes. Thinly slice crosswise. Spoon chimichurri over.