To bring this entire recipe together, I suggest making the candied jalapenos and bacon jam first. You can even do it a day before. Once that’s ready, prepare your soup and while it cooks, make your grilled cheese.
To make the candied jalapeños, Add the vinegar, sugar and garlic powder to a small saucepan over medium heat and whisk until the sugar dissolves. Allow the mixture to boil for 2 to 3 minutes, then add in the peppers and stir with a wooden spoon, making sure all of the slices are submerged. Cook for 3 to 4 minutes. Remove the peppers with a slotted spoon and place them in a jar or a bowl. Continue to cook the liquid for another 5 minutes until it has reduced by half, then pour it over the jalapeños. Allow the peppers to cool completely – you can do this a day ahead of time too.
Heat a large dutch oven over medium-low heat and add the bacon. Cook until the fat is started to render and a few pieces of the bacon are crispy. Stir in the onion, paprika, salt and pepper and cook for 5 minutes. Stir in the brown sugar and cook for another minute or so.
Stream in 3/4 cup bourbon and 1/2 cup of chicken stock, stirring with a wooden spoon to release any bits of flavor from the bottom of the pot. Simmer the mixture, stirring occasionally, for about 10 minutes until the liquid has evaporated and the mixture has thickened. Stir in the remaining bourbon and 1 cup of stock, cooking again for 10 more minutes while stirring, until that liquid has evaporated too. Add the last of the chicken stock.
Transfer the mixture to a blender and very carefully, blend until pureed. (I put a towel over the top and hold it down.)
Return the mixture to the same pot and cook for another 10 minutes until it has cooked down a bit more and thickened. Taste and add more salt and pepper if needed. Stir in the butter. Let cool completely before scooping into an airtight container and storing in the fridge.
To make the grilled cheese, heat a griddle or skillet over medium-low heat. To assemble the sandwich, spread one of the inside slices with bacon jam. Top with the grated cheese and a few spoonfuls of the jalapenos. Cook until the bread is toasty and golden brown and the cheese is melted. Serve with a soup dipper!