Prepare a medium hot fire in a charcoal grill with a cover, or preheat a gas grill to medium high.
In a large mixing bowl, whisk together the mayonnaise and cream cheese until smooth. Stir in the cheese, pimiento peppers, and bacon. Add salt and pepper to taste. (This will make way more than you will need for the burgers. Makes a great dip or sandwich spread.)
To make the patties, combine the beef, chopped onion, wine, Worcestershire sauce, 4 teaspoons salt, and 4 teaspoons cracked black pepper in a large bowl. Handling the meat as little as possible, mix well. Form into 16 equal portions and shape the portions into patties. Lay 8 patties on a large baking sheet that has been covered in wax paper or foil. Place a small amount of the pimiento cheese spread (about a tablespoon) in the center of each patty. Place the remaining patties on top of the cheese and pinch the sides of the meat to seal well.
Brush the grill rack with vegetable oil. Place patties on grill rack, cover, and cook, turning once, until done to preference, about 5-7 minutes on each side for medium. Toast buns on grill rack the last few minutes of cooking. Dress burgers with lettuce, onion, and tomatoes and your choice of condiments. 8 burgers.