2 lb. mixed-size cherry tomatoes, on the vine if desired (about 4 pints)
4 large garlic cloves, crushed
1/4 c. plus 1 tbsp. extra virgin olive oil
1/4 tsp. crushed red pepper
Kosher salt and black pepper
1 1/2 lb. chicken breast cutlets (about 1/3″ thick)
1 1/2 tbsp. chopped tarragon
Heat oven to 500°F. Heat grill on medium-high. Cut about 1 cup of largest tomatoes in half. On rimmed baking sheet, toss all tomatoes with garlic, 1/4 cup olive oil, red pepper and 3/4 teaspoon salt.
Roast on upper oven rack, stirring halfway through, until tomatoes burst and soften and some are beginning to char, about 20 minutes. (If most juices have evaporated, stir in 1 to 2 tablespoons water to create more sauce.)
Meanwhile, coat chicken cutlets with remaining tablespoon olive oil and season with 1/4 teaspoon each salt and black pepper. Grill until lightly charred and just cooked through, 2 to 3 minutes per side.
Gently toss tomatoes with chopped tarragon. Spoon tomatoes and juices on top of chicken.