Place the bread in a food processor or blender. With the machine running add the vinegar, garlic, sugar and chili, and blend until smooth.
Add the extra virgin olive oil until the bread will absorb no more then, a little at a time, add the tomatoes, tomato ketchup, tomato juice, spring onions, red pepper, cucumber and pesto. Continue to blend to form a smooth emulsion. Season to taste with salt and black pepper.