Preheat your oven to 400°F and line a large rimmed baking sheet with parchment paper for easy cleanup.
Pat the chicken breast completely dry with paper towels and season both sides with half of the sea salt, black pepper, garlic powder, and smoked paprika.
Trim the tough, woody ends off the asparagus spears so they are uniform in length.
Divide the asparagus into three small bundles and wrap one slice of bacon tightly around the center of each bundle, securing the ends underneath.
Place the seasoned chicken breast and the bacon-wrapped asparagus bundles onto the prepared baking sheet.
Drizzle the olive oil over the chicken and the exposed parts of the asparagus.
In a small ramekin, whisk together the maple syrup and the remaining spices to create a thick glaze.
Roast in the center of the oven for 15 to 18 minutes, or until the chicken is cooked through and the bacon starts to crisp.
During the final 3 minutes of roasting, brush the maple glaze generously over the bacon-wrapped asparagus bundles before returning to the oven to caramelize.