How to Make It
Preheat oven to 400°F. Heat olive oil in a 12-inch cast-iron skillet over medium. Sprinkle pork chops with salt and pepper, and add to hot oil. Sear pork chops until golden brown, 3 to 4 minutes on each side, lightly searing the sides to render some of the fat. Transfer pork chops to a plate.
Add tomatoes, fennel, thyme, and garlic to skillet over medium; toss to combine. Cook, scraping skillet to loosen browned bits, until fragrant, about 2 minutes. Remove and discard garlic. Place pork chops on top of vegetable mixture, and roast in preheated oven until a thermometer inserted in thickest portion of chops registers 145°F and vegetables are tender, 6 to 10 minutes.
Remove and discard thyme. Transfer pork chops to a plate, and let rest 5 minutes. Add red wine vinegar to vegetables, and stir to combine. Serve pork chops over vegetables, and top with reserved fennel fronds. For a heartier meal, serve over polenta.