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1
Preheat oven to 500F with rack in middle.
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2
Toss tomatoes with shallots, garlic, oil, and 1 1/2 teaspoons salt, 1 tsp freshly ground black pepper & pinch of crushed red pepper flakes in a shallow 3-quart baking dish, then arrange tomatoes cut sides up.
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3
Roast, uncovered, basting once, until tomatoes are tender but still hold their shape and are starting to brown, 35 to 45 minutes.
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4
Cool to room temperature.
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5
While tomatoes cool, prepare grill for direct-heat cooking over hot charcoal (medium-high heat for gas).
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6
Sprinkle each steak all over with 1/4 teaspoon salt and 1/4 teaspoon pepper (total per steak).
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7
Oil grill rack, then grill steaks, covered only if using a gas grill, turning over once, 5 to 6 minutes total for medium-rare.
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8
Transfer to a cutting board.
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9
Lightly brush both sides of bread slices with some of oil from roasted tomatoes and grill, covered only if using a gas grill, turning over once, until lightly toasted and grill marks form, about 1 minute total.
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10
Stir together vinegar and sugar until sugar is dissolved, then stir in herbs.
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11
Spread one side of each bread slice with some of herb mixture (about a tablespoon per slice).
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12
Slice steaks thinly & on a bias, then make into sandwiches with bread, roasted tomatoes and shallots, and arugula.
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13
Serve with an herbed potato salad, corn on the cob and a green vegetable, Seasoned Green Beans(we made them w/out basil)recipe #17425.
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14
*Tomatoes can be roasted 1 day ahead, cooled, and chilled, covered.
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15
Bring to room temperature before using.
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16
** Steaks can be cooked in a hot lightly oiled large (2-burner) ridged grill pan.
