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Steak: (A step ahead: Make the olive stuffing a day or two ahead and store it, covered, in the refrigerator.
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Stuff and tie the steaks early in the day and store them, covered, in the refrigerator.
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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.
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Add the onion and cook until soft and caramelized, stirring occasionally, about 10 minutes.
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Add the garlic and cook until aromatic, a few minutes more.
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Remove from the heat and transfer to a bowl.
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Stir in the olives, herbs, pine nuts and currants.
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Set aside to cool.
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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.
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The surface area of the steak should increase by only about 25 percent.
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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.
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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.
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Using kitchen twine, tightly tie the steak in 5 or 6 places to keep it securely rolled up.
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Season the outside of the steak with salt and pepper.
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Repeat with the other steak and the other half of the stuffing.
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To pan-sear and roast the steaks, preheat the oven to 400 degrees.
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Pour about 2 tablespoons of olive oil into a roasting pan and place the pan over two burners over medium-high heat.
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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.
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Remove the pan from the heat and transfer the steaks to a plate.
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Discard any fat in the pan and scrape out any burned bits that may have escaped from the stuffing.
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Put the steaks back in the roasting pan, put the pan in the oven, and roast, uncovered, for 7 to 8 minutes.
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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.
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Remove the pan from the oven and allow the steaks to rest for 5 to 8 minutes.
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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.
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Arrange the slices on a platter and pour any pan juices that have collected over the top.
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Serve the steak with the cherry tomato confit.
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CONFIT: (A step ahead: Make the confit up to 5 days ahead and store, with the oil, covered and refrigerated.
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The flavor improves significantly after 1 day.
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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.
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Put the tomatoes in a baking pan large enough to hold them in a single layer.
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Pour the oil over the tomatoes, add the herb sprigs and garlic cloves, and season generously with salt and pepper.
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Roast, uncovered, until the tomatoes are swollen and the skins are wrinkled, about 3 hours.
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Remove the tomatoes from the oven, allow to cool, then pour into a small bowl.
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For the best flavor, cover and refrigerate overnight, bringing the confit back to room temperature when you are ready to serve.
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When you are prepared to serve, pour the tomatoes into a strainer set over a bowl, reserving both the tomatoes and the oil.
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Place the drained tomatoes in a small bowl, discarding the herb sprigs and garlic cloves.
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Add the vinegar, chopped thyme, and 1 tablespoon of the reserved oil (reserving the rest for another use).
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Mix gently, being careful not to break up the tomatoes.
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Season to taste with salt and pepper.
