Place tomatoes on a sheet pan covered with parchment paper, cut side up.
Drizzle with a small amount of EVOO and balsamic vinegar, 2 minced cloves of garlic, kosher salt, pepper, and a light sprinkle of sugar.
Roast at 450’for 25-30 minutes until tomatoes are concentrated and beginning to caramelize. Cool and cut into chunks.
While tomatoes are roasting, heat oil in a large saute pan. Add bread cubes and salt and cook over low-medium heat tossing frequently for 10 minutes until lightly browned on all sides. Add more oil if needed.
Mix all salad ingredients and dress, adding croutons and tomatoes just before serving.