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Preheat your oven to 375°F (190°C) and lightly grease a 9x13-inch baking dish.
Pat the pork chops dry with paper towels and season both sides generously with salt and black pepper. Heat olive oil in a large skillet over medium-high heat. Sear the pork chops for 2 to 3 minutes per side until golden brown. Transfer them to the prepared baking dish.
In a small bowl, whisk together the reserved pineapple juice, brown sugar, soy sauce, minced garlic, ketchup, and ground ginger until the sugar mostly dissolves.
Place one pineapple ring flat on top of each seared pork chop. Pour the sweet brown sugar glaze evenly over the chops and pineapples, letting it pool in the bottom of the dish around them.
Bake uncovered for 15 to 20 minutes (depending on thickness), or until the internal temperature of the pork reaches 145°F (63°C). Spoon the pan juices over the top of the pineapples halfway through baking.
Let the pork chops rest for 5 minutes before serving. Drizzle with extra pan sauce over a bed of fluffy white rice if desired.