Position a rack in the center of the oven and preheat the oven to 500 degrees F (or the highest setting).
Bring the steaks to room temperature.
Meanwhile, remove 1 garlic clove from the bulb and finely grate. Remove the other cloves with the skin still intact and spread them on a baking sheet along with the tomatoes. Toss with about 1/4 cup EVOO and season with salt and pepper. Turn the tomatoes cut-side down. Roast until the tomatoes are charred and softened, 20 to 25 minutes.
Lightly toast the pine nuts in a small skillet over medium heat, then remove to a plate to cool.
Combine the parsley, basil, endive, radicchio, thyme, pine nuts, lemon juice and cheese in a food processor. Season with salt and pepper. Pulse until chopped. With the motor running, drizzle in the remaining 1/2 cup EVOO in a slow stream until blended. Transfer the pesto to a serving dish. (Any leftover pesto is delicious on sandwiches or tossed with hot pasta and starchy cooking water.)
Heat a grill pan or heavy griddle over medium-high heat or prepare an outdoor grill.
Drizzle the steaks with EVOO and sprinkle with salt and pepper. Grill for 3 to 4 minutes, then flip and cook 3 more minutes for medium-rare. Remove to a cutting board and let rest for 5 to 10 minutes.
Place the steaks on serving plates and drizzle with the pesto. Serve the roasted tomatoes, garlic and bread on the side. To eat, squeeze the garlic from the skins and rub onto the bread, then top with the tomatoes.
Recipe courtesy of Rachael Ray