Preheat the oven to 450 degrees
In a large mixing bowl, toss the tomatoes, sliced
onions, kalamata olives, 2 tablespoons of olive oil, 1 tablespoon of white balsamic vinegar, 2 tablespoons of parsley, and some black pepper. Mix well and pour into a baking dish. Bake 20 to 25 minutes, or until onions carmelize and tomatoes brown. Pull from the oven and set aside.
In a large sauce pan, heat 1 tablespoon of olive oil over medium heat. Add the garlic and the remaining parsley and cook until the garlic softens. Add the squid and saute, turning over a few times. Add pepper to taste. After 5 minutes, add the white wine. Turn the heat down to medium-low, cover, and simmer 20 to 25 minutes. When the squid is tender all the way through, take it off the heat. Set aside.
With a slotted spoon, take the squid out of the saute pan and put into a medium mixing bowl. Set aside the liquid in the saute pan from the cooked squid for the dressing.
Pour out 1/4 cup of the reserved squid juices into a small mixing bowl. Add the squid to the large mixing bowl with the tomato/olive mixture. Toss in the remaining olive oil, white balsamic vinegar, lemon juice, and more black pepper to taste.
Pour the dressing over the squid mixture. Toss with more parsley and add salt and pepper to taste. Serve as a warm salad.