Remove the base and stem of the pineapple. Place the pineapple on a cutting board, remove the outer rind, and separate the flesh from the core. Slice the remaining pineapple flesh into long, thin strips (roughly the same size as each pork chop).
In a high sided pan, heat 1 Tbsp of oil and brown the seasoned pork chops on medium high heat for approximately 3 minutes on each side. Set the chops aside on a plate, add another tablespoon of oil to the pan, and brown pineapple slices on each side for 1 minute, remove from the pan, and place on top of the pork chops.
Place the pineapple topped pork chops back in the pan and season lightly with pepper. Top with slices of cheese, cover, and simmer on medium heat for 2-3 minutes.
Top with cherry tomato slices and serve.