In a bowl, combine the tomatoes and Maui onion. Season with salt and pepper and toss to combine. Add the Maui Onion Dressing and toss to combine. Place the greens on a large platter and season with salt. Top with the tomato salad and serve.
Preheat the oven to 350 degrees F. Place the onion on a large piece of aluminum foil. Drizzle the onion with 2 tablespoons of the olive oil and season with salt and pepper. Wrap the onion tightly in the foil and roast until tender and lightly golden brown, about 50 minutes to 1 hour.
Remove from the oven and cool. When cool, roughly chop the onion and place in the bowl of a food processor. Process until smooth. With the machine running, slowly add the remaining 1/4 to 1/2 cup olive oil through the feed tube, until the dressing is smooth. Season with salt and pepper.