Garlic Fennel Flank Steak with Oranges

Chef John's recipe for garlic fennel flank steak with oranges draws inspiration from Italian, Spanish, and Chinese cuisines.

• Preparation Time: 15 mins
• Cooking Time: 15 mins
• Total Time: 30 mins
• Calories: 319 Calories

Ingredients

• 2 teaspoons salt
• 2 tablespoons olive oil
• 2 tablespoons ground black pepper
• 1 tablespoon fennel seed
• 4 cloves garlic, crushed
• 1 pinch cayenne pepper, or to taste
• 1 tablespoon olive oil, or as needed
• 1 (2 pound) flank steak
• 1 orange, juiced
• 2 oranges, halved
• 4 sprigs rosemary, leaves stripped and bruised

Recipe Instructions

Step 1

Preheat an outdoor grill for medium-high heat and lightly oil the grate.

Step 2

Grind black pepper and fennel seed together in a mortar with a pestle. Pour half the pepper mixture into a small bowl and stir in salt.

Step 3

Stir remaining pepper mixture, garlic, rosemary, 2 tablespoons olive oil, orange juice, and cayenne pepper together in a bowl.

Step 4

Rub rosemary mixture over both sides of flank steak, poking mixture into steak several times with a fork. Transfer steak to a resealable plastic bag and marinate in the refrigerator for 2 hours. Remove steak from marinade; scrape off and discard any excess marinade.

Step 5

Sprinkle reserved pepper-fennel mixture over steak. Drizzle 1 tablespoon olive oil over orange halves.

Step 6

Cook steak on the preheated grill until it begins to firm and is reddish-pink and juicy in the center, about 5 minutes per side. An instant-read thermometer inserted into the center should read 130 degrees F (54 degrees C). Remove to a plate to rest for 10 to 15 minutes before slicing across the grain.

Step 7

Place oranges, flesh-side down, on the grill and cook until flesh is golden and caramelized, 3 to 5 minutes. Place steak and 3 orange halves on a serving platter. Squeeze remaining caramelized orange half over the steak.