Pat the pork chunks completely dry with paper towels and season generously with salt and pepper. Dust the pork pieces lightly with flour, shaking off any excess.

Heat a large Dutch oven or heavy-bottom pot over medium-high heat. Add the chopped bacon and cook until crispy and the fat has rendered, about 6-8 minutes. Remove the bacon with a slotted spoon and set aside, leaving the bacon fat in the pot.

Working in batches to avoid crowding, add the floured pork chunks to the hot bacon fat. Sear until deeply golden brown on all sides, about 3-4 minutes per side. Remove the browned pork and set aside with the bacon.

If the pot looks dry, add the olive oil. Add the minced garlic and cook for 30 seconds until fragrant. Add the bourbon to deglaze the pot, scraping up all the browned bits from the bottom. Let the bourbon reduce by half, about 2-3 minutes.

Return the pork and bacon to the pot. Add the balsamic vinegar, beef broth, brown sugar, thyme leaves, and bay leaf. Stir to combine, then bring the mixture to a boil.

Once boiling, reduce the heat to low, cover the pot with a tight-fitting lid, and let the stew simmer gently for 1.5 hours, stirring occasionally.

After 1.5 hours, add the sliced apples and prunes to the pot. Stir gently to incorporate, then cover and continue simmering for another 30-45 minutes until the pork is fork-tender.

Remove the bay leaf and discard. Taste the stew and adjust seasoning with additional salt and pepper if needed. If the sauce seems too thin, simmer uncovered for 10-15 minutes to reduce and thicken.

Let the stew rest for 10 minutes before serving. Serve hot in deep bowls with plenty of sauce.