Trim and rinse the leeks. Pat dry as they can be with a paper towel.
Heat a large pot over medium-low heat and add the olive oil and butter. Add the leeks, salt, pepper and crushed pepper flakes and toss well to coat. Cook, stirring every few minutes, until the leeks begin to brown, about 20 to 25 minutes. Once the leeks are starting to brown, stir in the brown sugar and cook for another 10 minutes until they are super caramelized. Stir in the roasted garlic. Increase the heat slightly to medium and add the wine. Stir to combine, then cook for a few minutes until most of the wine cooks off. Pour in the stock and stir. Bring the soup to a boil, then reduce to a simmer and cook for 15 minutes.
Turn off the heat and carefully add the entire mixture to a blender and puree until smooth. Pour the pureed soup back in the pot and heat it over low heat. Stir in the half and half, then tasted and add more salt and pepper if desired.
To prepare the maple glazed bacon preheat oven to 375 degrees F.
Line a baking sheet with aluminum foil and place a nonstick wire rack on top. Bake for 18 to 20 minutes, until bacon is starting to get crispy in parts and the fat is rendered. Remove the bacon from the oven and brush it on both sides with maple syrup. Bake for another 6 to 8 minutes until the bacon is crispy and dark. Remove from the oven and brush with maple syrup once more, then let cool completely. Once cooled, crushed into bits.
Serve and enjoy!