The steak and wheat berries are refrigerated overnight in a marinade made with substantially spicy chipotle chiles in adobo, so plan accordingly.
1 cup whole wheat berries (7 ounces)
3 cups water
1 large tomato--peeled, seeded and chopped
3 chipotle chiles in adobo sauce, seeded and chopped, plus 1 tablespoon of the sauce
1/2 cup tomato paste
2 tablespoons fresh lemon juice
2 teaspoons honey
1 large garlic clove, minced
1/2 teaspoon cinnamon
1/4 teaspoon ground cumin
3 tablespoons plus 1 teaspoon extra-virgin olive oil
Salt and freshly ground pepper
One 2-pound sirloin steak
2 teaspoons white wine vinegar
16 cherry tomatoes, halved (1/2 pound)
1 medium cucumber--peeled, seeded and cut into 1-inch dice
2 tablespoons coarsely chopped flat-leaf parsley
How to Make It
In a medium saucepan, combine the wheat berries with the water and bring to a boil. Cover and simmer over low heat until the wheat berries are tender but still chewy, about 2 hours.. Drain and let cool to room temperature.
Meanwhile, in a mini food processor, puree the chopped tomato with the chipotles and adobo sauce. Transfer to a medium bowl. Stir in the tomato paste, lemon juice, honey, garlic, cinnamon and cumin. Add 3 tablespoons of the olive oil; season with salt and pepper.
Put the steak in a shallow dish and coat with 1/4 cup of the tomato-chipotle sauce. Stir the wheat berries into the remaining sauce and season with salt. Cover and refrigerate the steak and wheat berries overnight.
Light a grill or preheat a grill pan. Bring the steak and wheat berries to room temperature. Oil the grill and cook the steak over a medium-hot fire for about 4 minutes per side, or until lightly charred on both sides and medium rare within. Transfer the steak to a cutting board and let rest for 5 minutes.
In a medium bowl, mix the vinegar with the remaining 1 teaspoon of olive oil. Add the cherry tomatoes, cucumber and parsley, season with salt and pepper and toss well. Slice the steak 1/4 inch thick and serve with the wheat berries and the tomato salad.
Make Ahead: The tomato-chipotle sauce and the wheat berry salad can be refrigerated for up to 3 days.
Wine Recommendation: The rare steak and intense tomato dressing point to an equally rich red wine, with plenty of ripe fruit. Choose a juicy, supple Syrah from Washington State, one without too much tannin or smoky oak, such as the bargain 2000 Snoqualmie or the 1999 Hogue.
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