Heat broiler. Cut pork into 1x4-inch strips that are ¼-inch thick. Cut bacon slices in thirds.
Place one slice of bacon on top of each slice of pork; thread onto skewers. Sprinkle bacon with chipotle powder.
Place skewers, bacon side up, on rack in broiler pan. Broil, 4 to 6 inches from heat until bacon is done but not crisp, about 5 minutes. Turn and broil until pork starts to brown. Turn back to bacon on top and broil until bacon is crisp.