To prepare the crumbles, heat a tablespoon of olive oil in a cast iron skillet on a medium grill and fry the country ham until brown and crispy. Remove the pieces and drain on a paper towel to crisp. Brush asparagus spears with olive oil, sprinkle with a pinch of salt and place on a hot grill for 3-4 minutes on each side. Remove to a serving dish. To make the vinaigrette, whisk together mustard, vinegar, molasses, bourbon, salt, pepper, and shallot until incorporated. Slowly drizzle in all but a tablespoon of the olive oil in a thin stream, continually whisking until the mixture has emulsified.