Cut the cherry tomatoes in half and toss them in a bowl with the sugar. Let them sit at room temperature for about 1 hour, stirring once or twice during this time.
Heat a large non-stick skillet over medium-high heat. Add tomatoes, any accumulated juices and shallots. Cook, stirring frequently for 12-15 minutes, or until the jam is thick, glossy and the tomatoes are almost broken down.
Stir in remaining ingredients and cook for an additional 1-2 minutes. Remove from the heat and set aside.
Once cooled, the tomato-shallot jam can be stored in an airtight container in your refrigerator for 7-10 days. This recipe makes enough jam for 6-8 burgers.
Pre-heat grill to high.
Add ground beef, brown sugar, Worcestershire sauce, olive oil and about 1/2 teaspoon salt and black pepper to a medium bowl. Using your hands, combine the ingredients together, being careful not to over mix. Form the mixture into 3 or 4 patties, depending on your preferred burger size. Sprinkle the tops of the patties with additional black pepper.
Add burger patties to the grill and cook for 4-5 minutes per side. During the last minute, add one Castello Blue Cheese Slice to each burger. You can also add hamburger buns to the grill at this time for a lightly toasted effect. Remove burgers and buns from the grill.
Spread some tomato-shallot jam onto the bottom half of each hamburger bun. Top with lettuce, burger patties, French fries (if desired) and the top half of the hamburger bun.