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Three slices of rolled and stuffed flank steak with visible herbs, spinach, and bacon, garnished with salt and surrounded by fresh spinach and seasoning.
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Grilled Flank Steak Pinwheels

This may be the fanciest way to grill a 'steak.' Butterflied flank steak layered with bacon, prosciutto, mushroom saute, provolone, and pesto, rolled tight, sliced, and grilled to perfection.
Prep Time25 minutes
Cook Time10 minutes
freeze time15 minutes
Total Time45 minutes
Course: Main Course
Cuisine: American, BBQ
Servings: 5 servings (1 pinwheel per serving)
Calories: 673kcal
Author: Brittany Lauren

Equipment

Ingredients

For the Filling

  • 1/2 to 1 lb bacon, uncooked
  • 2 tbsp reserved bacon fat
  • 1 medium onion, diced
  • 8 white button mushrooms, diced
  • 2-3 cloves garlic, minced

For the Pinwheels

  • 2 to 2.5 lbs flank steak
  • 2 tbsp Worcestershire sauce
  • 6 oz prosciutto, thin-sliced
  • 1/2 tbsp steak seasoning
  • 1 to 1.5 cups raw spinach
  • 12 thin slices provolone, cold
  • 2 tbsp pesto
  • 1 tsp dried rosemary
  • Kosher salt, to finish

Instructions

Chill the Steak

  • Place flank steak on a baking sheet and freeze 10-15 minutes until semi-firm. This helps when slicing.

Cook the Filling

  • Fry bacon in batches over medium heat until cooked but still pliable, 4-5 minutes per batch. Reserve 2 tablespoons drippings.
    Six strips of bacon cooking in a white frying pan on a wooden surface.
  • Sauté the onion, mushrooms, and garlic in bacon fat over medium-high heat until onions are translucent and mushroom moisture has cooked off, 5-8 minutes. Cool to room temperature.
    A white frying pan with chopped mushrooms and onions cooking in oil on a wooden surface.

Butterfly the Steak

  • Cut along the long edge, slicing horizontally toward the opposite side without cutting through. Open flat to 1/4 inch thickness; it should look like an open book. If your piece is uneven or too thin to butterfly, pound with a mallet to create a large, thin rectangle.

Preheat Grill

  • Heat grill to 450 - 500 degrees F.

Layer and Roll

  • Brush the inside surface with Worcestershire sauce.
  • Then layer in this order: prosciutto, seasoning, spinach, mushroom/onion/garlic mixture, provolone cheese, pesto, and bacon.
    A wooden cutting board holds a butterflied flank steak layered with spinach, sauteed mushroom filling, and six slices of cheese.
  • Starting at the long end, tightly roll the flank steak up, pushing the fillings in as you roll.
    Raw flank steak rolled up with filling on a wooden cutting board.

Skewer and Slice

  • Thread skewers through the roll at even intervals. Slice between skewers into 5-6 pinwheels.
    Eight raw beef pinwheels with spinach and cheese are arranged on metal skewers on a wooden cutting board; a hand is holding one skewer.

Grill

  • Place the pinwheels with the skewers on the grill, cover and cook, rotating for 2 ½ minutes per side, or until desired doneness.
    For medium rare, cook until the internal temperature reaches around 130 degrees F. 
    Three rolled and stuffed flank steak pinwheels on skewers are grilling over open flames on a barbecue grill.

Rest & Serve

  • Rest 10 minutes before removing skewers and serving.

Notes

  • Make ahead: Roll the whole log, wrap tightly, refrigerate up to 8 hours. Slice immediately before grilling.
  • The par-freeze step matters: a cold steak butterflies in a straight line; room-temperature meat is harder to slice evenly.
  • Refrigerate in airtight container up to 4 days. Freeze individually wrapped up to 3 months.
  • Reheat at 325 degrees F on a wire rack, 10-12 minutes to 130 degrees F. Avoid the microwave.
Charcoal grill: Bank coals to one side so you have a safe zone if the cheese starts running. Direct heat over hot coals gives a better sear on the cut faces than gas.
Gas grill: Preheat all burners to high, then cut the center burner off once the pinwheels are on. This gives you direct heat on the cut faces without the flare-ups that melting cheese causes over an open flame.

Nutrition

Serving: 1serving | Calories: 673kcal | Carbohydrates: 7g | Protein: 51g | Fat: 48g | Saturated Fat: 17g | Polyunsaturated Fat: 6g | Monounsaturated Fat: 20g | Trans Fat: 0.1g | Cholesterol: 169mg | Sodium: 799mg | Potassium: 1009mg | Fiber: 1g | Sugar: 3g | Vitamin A: 669IU | Vitamin C: 6mg | Calcium: 92mg | Iron: 4mg