Preheat oven to 425F. Line a baking sheet with parchment paper. In a large bowl toss brussels with olive oil, salt and pepper and add them to the baking sheet in a single layer.
Bake until Brussels begin to brown on the edges - 20-25 minutes. Remove from oven and set aside.
Heat a dutch oven or large skillet over medium heat and add in bacon. Cook, stirring occasionally, until bacon is fully cooked and crisp - 8-10 minutes.
Using a slotted spoon, remove crisp bacon bits from pot/pan and allow to cool, until ready to use again, on a paper towel-lined plate. Pour balsamic and bourbon into the pot and scrape up the browned bits from the bottom of the pan. Bourbon and balsamic will bubble rapidly.
Add in maple syrup and brown sugar. Stir occasionaly until the sauce has thickened, 5-7 minutes.
Turn off the heat and add in cooked brussels, crisp bacon bits and slivered almonds. Stir well to combine. Season with salt and pepper as needed.
When you're ready to serve, plate your brussels on a platter and top with heaping spoonfuls of pomegranate salsa.