Put wings, half of garlic and 1 teaspoon sea salt in a sealable plastic bag. Use hands to massage wings with garlic and salt. Set aside in refrigerator for 2 hours.
Remove chicken from bag and pat dry, reserving garlic. In large pan over medium high heat, warm ¼ cup olive oil. Add wings in single layer, and cook until golden brown, about 10 minutes. Transfer wings to large bowl, and set aside.
Pour remaining ¼ cup oil in pan, then add reserved and remaining garlic. Cook until garlic begins to change color. Do not let garlic burn. Add tomatoes with juices, crushing gently. Stir to scrape browned bits from bottom of pan, and add wings. Add parsley, oregano, 1 teaspoon salt, black pepper and red pepper flakes. Cook until wings are cooked through and sauce coats thickly, about 10 minutes. Season with salt, to taste. Serve immediately, or enjoy later at room temperature or chilled in refrigerator. Serves 4.
Marchesi Antinori 2018 Pian delle Vigne (Rosso di Montalcino). Though Rosso di Montalcino is the less-exalted younger sibling of Brunello di Montalcino, this pairing is a good example of where its easy drinkability can make it the better choice. Both are made from 100% Sangiovese, but Rosso di Montalcino tends to be less tannic and concentrated, and is aged for just one year with no oak requirements. This bottle shows dried herb and spice notes that go well with this flavorful dish.