Flank steak is a very versatile and lean cut of steak, so it really benefits from a marinade. The marinade helps tenderize the meat and infuse it with flavor. Poking the steak with a fork here helps the marinade penetrate better and faster. Double cooking sweet potatoes in both the microwave and the grill, yields the creamiest insides and crisp charred skin.
Put the steak in a resealable plastic bag along with the garlic, 2 tablespoons bourbon, the brown sugar, Worcestershire sauce, chili powder, cumin, 1/2 teaspoon salt and a few grinds of pepper. Rub the marinade into the steak and refrigerate, 6 to 12 hours.
Preheat a grill to medium high. Remove the steak from the marinade; pour the marinade into a small saucepan, discarding the garlic. Add 2 tablespoons water and the remaining 2 tablespoons bourbon. Bring to a boil, reduce the heat and simmer until slightly reduced, 3 to 5 minutes. Remove from the heat, stir in the vinegar and season with salt and pepper. Meanwhile, prick the sweet potatoes with a fork and microwave until soft, 5 to 7 minutes.
Season the steak with salt and pepper. Toss the broccolini with the melted butter and season with salt and pepper. Grill the steak, turning once, 10 to 12 minutes for medium rare, and the sweet potatoes, turning, until charred, 15 to 18 minutes. Once the steak is done, grill the broccolini, turning, until tender, 6 to 8 minutes.
Thinly slice the steak and divide among plates; spoon the reduced marinade on top. Serve with the broccolini and sweet potatoes; top the sweet potatoes with butter.
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Photograph by Andrew Purcell
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