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1
Pound the steak on both sides with a meat tenderizer or pierce with a fork.
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2
Transfer to a large resealable plastic bag; add 2 tablespoons olive oil, the lemon juice, 1/2 teaspoon salt and a few grinds of pepper.
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3
Seal the bag and shake to coat; marinate in the refrigerator, 2 to 8 hours.
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4
Meanwhile, make the pesto: Toast the pine nuts in a small skillet over medium-high heat, tossing occasionally, until slightly golden, about 3 minutes; let cool.
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5
Pulse the parsley, garlic and red pepper flakes in a food processor until almost smooth.
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6
Add the toasted pine nuts, cheese and 5 tablespoons olive oil and pulse until combined.
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7
Transfer to a bowl and stir in 3 tablespoons water and the olives; season with salt.
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8
Remove the steak from the marinade and pat dry.
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9
Bring to room temperature, about 30 minutes.
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10
Heat a large cast-iron or other heavy skillet over medium-high heat; add the remaining 1 tablespoon olive oil, then add the steak and cook until a dark crust forms, about 7 minutes.
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11
Turn and cook until a thermometer inserted into the center of the steak (from the side) registers 130 degrees F for medium rare, about 8 more minutes.
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12
Transfer to a cutting board and let rest 10 minutes.
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13
Brush the steak with some of the pesto.
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14
Thinly slice against the grain and serve with the remaining pesto.
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15
Photograph by Anna Williams