I created this sandwich one day when I was looking to make an impressive sandwich for a lunch time event at my home. I started with the classic Dagwood, then “kicked it up a notch!” I sliced each sandwich in half and arranged them on a large serving platter. I love how every layer adds a different texture and taste. The sweet-tangy raspberry-basil-mustard is what brings it all together. If you’d like, you can garnish with fresh, whole raspberries.
In a medium bowl, add tomato slices. Sprinkle with sugar and salt. Let sit while preparing sandwich.
In a medium bowl, stir together raspberry preserves, mustard, and basil until well combined.
In a large, nonstick skillet, over medium high heat, heat olive oil. Add onions. Cook, stirring occasionally, 5-6 minutes or until soft and tender. Remove from heat; transfer onions to a plate.
Wipe skillet clean. Spread butter over both sides of bread slices. Place on skillet, over medium heat; toast lightly on both sides, about 3 minutes.
To assemble: Spread raspberry-mustard on one side of 2 bread slices. Top each with arugula, one slice of Monterey Jack cheese, layer 2 slices of pastrami, tomato slices, and peperoncini. Spread raspberry-mustard on one side of 2 bread slices; place raspberry-mustard side up on each sandwich. Top each with 2 slices Gouda cheese, layer 2 slices smoked turkey, arugula, and sautéed onions. Sprinkle each sandwich with black pepper to taste. Close with remaining bread slices. Use a toothpick to secure a basil leaf and a black olive on top of each sandwich.