Bourbon and Soy Marinated Flank Steak with Balsamic Caramelized Onions

Bourbon and Soy Marinated Flank Steak with Balsamic Caramelized Onions
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Ingredients for flank steak
  1. 1 flank steak, about 2 pounds
  2. 1/4 cup Worcestershire sauce
  3. 1/3 cup bourbon
  4. 1/4 cup soy sauce
  5. 1/4 cup dark brown sugar
  6. 4 anchovy filets
  7. 2 garlic cloves, smashed
  8. 2 tablespoons of Dijon mustard
  9. 2 tablespoons of tomato paste
  10. 1/2 cup canola oil
Ingredients for caramelized onions
  1. 1 tablespoon of butter
  2. 1 large onion, cut in half lengthwise, then cut crosswise in thin slices
  3. 1 tablespoon of brown sugar
  4. 2 tablespoons of balsamic vinegar
  5. 3-4 thyme sprigs
  6. salt and pepper, to taste
Instructions
  1. To make marinade, in a blender or using an immersion blender combine all ingredients, except flank steak, until smooth and emulsified. Pour one-third of marinade in separate bowl and set aside. Pour remaining marinade in sturdy gallon size zip lock bag. Add flank steak to bag with marinade. Press air out of bag, seal bag and turn to coat steak. Let steak marinate in refrigerator for 1 to 4 hours.
  2. While steak is marinating, make onions. Heat butter in a large sauté pan over medium-low heat. Add sliced onions and thyme sprigs to the pan and toss onions to coat in butter. Season with salt and pepper and cook onions until soft, about 15-20 minutes, stirring occasionally. Onions should be al dente, with a bit of a bite. Add sugar and balsamic vinegar and cook, stirring frequently, until onions caramelize, about 10 minutes. Remove thyme sprigs and season to taste with salt and pepper.
  3. To cook steak, preheat oven to 450 degrees. Set a wire rack in a foil lined rimmed baking sheet. Remove steak from marinade and pat dry with paper towels. Heat 2 tablespoons canola oil in cast iron skillet over high heat until shimmering. Add steak to hot pan and sear on both sides. Once both sides have a deep brown sear move to wire rack in baking sheet and transfer to oven. Cook until steak registers 125 degrees for medium rare, or 135 degrees for medium. Remove steak from oven and let rest on wire rack for 5-10 minutes. Cut steak against the grain on a bias. Move to serving platter, top with caramelized onions and drizzle with a few tablespoons of reserved marinade, passing remaining marinade at the table.
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