Olive Stuffed Flank Steak With Cherry Tomato Confit

“This is an adopted recipe. IHHDRO.”
3hrs 16mins

Ingredients Nutrition


  1. Steak: (A step ahead: Make the olive stuffing a day or two ahead and store it, covered, in the refrigerator. Stuff and tie the steaks early in the day and store them, covered, in the refrigerator. Bring the steaks to room temperature about 1/2 hour before cooking) To make the stuffing: Heat the 2 tablespoons oil in a saute pan over medium heat.
  2. Add the onion and cook until soft and caramelized, stirring occasionally, about 10 minutes.
  3. Add the garlic and cook until aromatic, a few minutes more.
  4. Remove from the heat and transfer to a bowl.
  5. Stir in the olives, herbs, pine nuts and currants.
  6. Set aside to cool.
  7. To prepare the flank steaks for stuffing: Place one of the steaks on a work surface, cover it loosely with a piece of plastic wrap, and use a meat pounder to pound the steak until about 1/3 inch thick.
  8. The surface area of the steak should increase by only about 25 percent.
  9. Then, use your knife to score the steak in a crisscross pattern, making 3 or 4 shallow cuts in each direction, not cutting all the way through.
  10. Turn the steak over to the unscored side and spread half the stuffing evenly over the surface of the steak, then roll it up the long way, like a jelly roll.
  11. Using kitchen twine, tightly tie the steak in 5 or 6 places to keep it securely rolled up.
  12. Season the outside of the steak with salt and pepper.
  13. Repeat with the other steak and the other half of the stuffing.
  14. To pan-sear and roast the steaks, preheat the oven to 400 degrees.
  15. Pour about 2 tablespoons of olive oil into a roasting pan and place the pan over two burners over medium-high heat.
  16. When the oil is hot, put the steaks in the pan and sear them well on all sides, turning with tongs, until nicely browned, 6 to 8 minutes.
  17. Remove the pan from the heat and transfer the steaks to a plate.
  18. Discard any fat in the pan and scrape out any burned bits that may have escaped from the stuffing.
  19. Put the steaks back in the roasting pan, put the pan in the oven, and roast, uncovered, for 7 to 8 minutes.
  20. Turn the steaks over and continue to roast until the internal temperature of the steaks reads between 120 degrees and 130 degrees on an instant-read thermometer, after 7 to 8 minutes more.
  21. Remove the pan from the oven and allow the steaks to rest for 5 to 8 minutes.
  22. Cut and remove the kitchen string, transfer the steaks to a cutting board, and use a sharp knife to cut them into slices 1/2 to 3/4 inch thick.
  23. Arrange the slices on a platter and pour any pan juices that have collected over the top.
  24. Serve the steak with the cherry tomato confit.
  25. CONFIT: (A step ahead: Make the confit up to 5 days ahead and store, with the oil, covered and refrigerated. The flavor improves significantly after 1 day. When you are ready to serve the confit, bring it back to room temperature, drain off the oil, and season as ) Preheat the oven to 225 degrees.
  26. Put the tomatoes in a baking pan large enough to hold them in a single layer.
  27. Pour the oil over the tomatoes, add the herb sprigs and garlic cloves, and season generously with salt and pepper.
  28. Roast, uncovered, until the tomatoes are swollen and the skins are wrinkled, about 3 hours.
  29. Remove the tomatoes from the oven, allow to cool, then pour into a small bowl.
  30. For the best flavor, cover and refrigerate overnight, bringing the confit back to room temperature when you are ready to serve.
  31. When you are prepared to serve, pour the tomatoes into a strainer set over a bowl, reserving both the tomatoes and the oil.
  32. Place the drained tomatoes in a small bowl, discarding the herb sprigs and garlic cloves.
  33. Add the vinegar, chopped thyme, and 1 tablespoon of the reserved oil (reserving the rest for another use).
  34. Mix gently, being careful not to break up the tomatoes.
  35. Season to taste with salt and pepper.

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