In a small sauce pan, add the dark brown sugar, pineapple juice, bourbon, soy sauce, and garlic powder and mix thoroughly. Bring the sauce to a low boil, then reduce to a simmer. Be sure to stir often while bringing the sauce to boiling so it doesn't burn.
Reduce the sauce by about half, 15 minutes or so.
Spoon a small amount of the bourbon glaze into a small bowl to use for basting the shrimp later on. This will prevent the majority from becoming contaminated form the raw shrimp as this will be used for the dipping sauce. Place the sauce in the fridge for an hour.
Heat the oven to 400 degrees and soak 30 toothpicks in water.
Place the bacon on 2 sheet pans. If you do not have 2 sheet pans, you can cook the bacon in batches.
Put the sheet pans in the oven and cook the bacon for 10-12 minutes. The fat should start to render and the meat should slightly begin to darken. Drain the bacon on a plate lined with paper towels. Cut each piece of bacon in half.
Season each shrimp with salt and pepper then wrap a piece of bacon around each one. Use a toothpick to hold the bacon in place.
Place a cooling rack on a sheet pan and spread the bacon wrapped shrimp on the rack. Using a basting brush, coat the side of the shrimp facing up with the bourbon glaze. Place the sheet pan in the oven and cook for 5 minutes.
Take the sheet pan out of the oven and turn the shrimp over. Brush the other side of the shrimp with the bourbon glaze. Put the pan back in the over and cook for another 5 minutes or until the shrimp are opaque.
Serve on a plate with the bourbon glaze as a dipping sauce. Garnish with chopped chives and enjoy!