Place a large skillet over medium-high heat with the olive oil. Season the pork chops liberally with salt and pepper and sear in the pan until deep golden brown and cooked through, about 5 minutes per side. Remove the chops to a plate and let them rest.
Return the same skillet to medium heat and add in the fennel, onion and caraway seeds. Saute, stirring frequently, until the vegetables begin to tenderize, 3 to 4 minutes. Add the mustard, vinegar and whiskey (if using) and continue cooking until the liquids have mostly reduced, 3 to 4 minutes more. Remove the pan from the heat and stir in the grated apple and reserved fennel fronds; adjust the seasoning as needed with salt and pepper.
Serve the pork chops over the warm fennel-apple slaw.
Grating the apple is a great way to save time when preparing this dish, especially since we're looking more for the flavor than the texture. Run it over the large holes of a box grater or through a food processor fitted with a grater attachment, just be careful not to do it more than a few minutes before adding it to the pan as the cut apple will begin to turn brown.