1. 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.
2. 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.
3. 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.
4. 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.
5. 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.