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Ingredients
- 1 cup red wine (or beef broth)
- 1 tablespoon sugar, divided
- ½ cup red wine vinegar
- 2–3 shallots, finely chopped
- 1 teaspoon kosher salt, divided
- ½ teaspoon pepper, divided
- 1 cup extra-virgin olive oil
- 2 oz fresh whole baby portabellas
- 2 oz fresh whole shiitake mushrooms
- 2 oz fresh whole cremini mushrooms
- 1 (24-oz) beef tenderloin
- ½ cup canola oil
- 1 teaspoon unsweetened cocoa powder
- 8 oz watercress (or arugula), torn into bite-size pieces
- 5 oz shaved Parmigiano-Reggiano cheese
Steps
- Combine wine and 1 teaspoon sugar in small saucepan; bring to boil on high. Reduce heat to medium-low and continue cooking, stirring occasionally, until reduced to syrup consistency (should yield about ¼ cup). Remove from heat and reserve.
- Whisk together vinegar, remaining 2 teaspoons sugar, shallots, ½ teaspoon salt, and ¼ teaspoon pepper until blended. Add olive oil in a slow stream, whisking constantly until combined. Reserve one-half of vinaigrette; add mushrooms to remaining one-half vinaigrette and toss to coat. Marinate 5 minutes.
- Preheat grill (or grill pan) on medium-high. Rub tenderloin with canola oil. Combine in small bowl cocoa powder, remaining ½ teaspoon salt, and remaining ¼ teaspoon pepper until blended. Season tenderloin with cocoa mixture. Place tenderloin on grill and cook 2–5 minutes on each side until 125°F (for medium rare; warm red center), 130°F (for medium; warm pink center), or up to 170°F (for well done).* Transfer to cutting board; let stand 5–10 minutes before slicing. Temperature will rise 5–10°F during this time.
- Strain mushrooms (discard marinade); grill 5 minutes, turning frequently, until golden brown. Transfer to cutting board and cool to room temperature. Cut portabellas into ½-inch-wide wedges, then halve shiitake and cremini mushrooms. Combine in large bowl: mushrooms and reserved one-half vinaigrette until well coated. Add watercress, cheese, and red wine reduction; toss to coat.
- To serve, slice tenderloin into ¼-inch slices and serve with salad on the side.
Amount per ¼ recipe serving: Calories 1240, Total Fat 106g, Sat Fat 21g, Trans Fat 1g, Chol 145mg, Sodium 1050mg, Total Carb 14g, Fiber 3g, Sugars 4g, Protein 55g, Calc 40%, Vitamin A 0%, Vitamin C 0%, Iron 30%