Grilled Steak & Roasted Tomato Sandwiches

Hope's in the kitchen's Note:

This interesting combination of sophisticated flavors makes an excellent sandwich. What I love is the tomatoes can be roasted ahead, chilled, and brought back to room temp, making this a excellent take-your-lunch-to-work option. -- modified from Gourmet magazine, August 2007.

• Total Time: 1 hrs 20 mins
• Prep Time: 20 mins
• Cook Time: 1 hrs

Ingredients:

Servings: 4

• 6 medium tomatoes , halved crosswise
• 3 shallots , thinly sliced into rings
• 3 garlic cloves , smashed
• ½ cup extra virgin olive oil
• 1 ½ teaspoons salt
• 1 ¾ lbs steaks , boneless (3/4-inch thick, approximately 3 total)
• 8 slices sourdough bread
• 2 tablespoons rice vinegar (not seasoned)
• 2 teaspoons sugar
• ½ cup finely chopped cilantro
• ½ cup finely chopped mint
• 1 bunch watercress , tough stems discarded

Directions:

1. Preheat oven to 500°F with rack in middle.
2. Toss tomatoes with shallots, garlic, oil and 1 1/2 teaspoons salt in a shallow 3 quart baking dish, then arrange tomatoes cut sides up. Roast uncovered, basting once, until tomatoes are tender but still hold their shape and are starting to brown, 35 to 45 minutes. Cool to room temperature.
3. Whole tomatoes cool, prepare grill for direct-heat cooking over hot charcoal (medium high heat for gas).
4. Sprinkle each steak all over with 1/4 t salt and 1/4 t pepper (total per steak). Oil grill rack, then grill steaks, coved only if using gas grill, turning once (5-6 min total for medium rare.
5. Transfer to a cutting board. Lightly brush both sides of bread slices with some oil from roasted tomatoes and grill, turning over once until lightly toasted and grill marks form (about 1 min total).
6. Stir together vinegar & sugar until sugar dissolves, then stir in herbs. Spread one side of each bread slice with some herb mixture (about 1 T per slice).
7. Slice steaks, then make into sandwiches with bread, roasted tomatoes, shallots, and watercress.