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1
For the steaks: Place the skirt steaks in a nonreactive container.
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2
Combine 1/4 cup oil, the Worcestershire, garlic, juice, mustard and shallots in a food processor and blend until smooth.
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3
Pour the mixture over the steaks, coating with the marinade.
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4
Marinate in the refrigerator for at least 4 hours or up to overnight.
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5
For the peppers and onions: Heat the oil over high heat in a saute pan and sear the peppers and onions for 2 to 3 minutes.
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6
Stir in the tarragon and rosemary.
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7
Sprinkle in the vinegar and toss to coat.
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8
Season with salt and pepper.
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9
For the salad and vinaigrette: Mix together the vinegar and red onions in a small stainless-steel bowl Pour the orange juice into a saucepan and cook until reduced to a syrup, and then let cool.
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10
Whisk the orange juice reduction and olive oil into the vinegar to create an emulsified vinaigrette.
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11
Add salt and pepper to taste.
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12
For cooking the steaks: Heat 1/8 cup olive oil in a cast-iron skillet until it just begins to smoke.
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13
Lightly sprinkle the steaks with salt and pepper and sear over high heat on each side until medium rare, 34 minutes per side.
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14
Combine the arugula, cherry tomatoes and vinaigrette in a bowl.
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15
Season with salt and pepper if necessary.
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16
Divide the salad among 46 dinner plates.
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17
Slice steak against the grain and place on the plates.
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18
Garnish with the peppers, onions and Cheddar.
