Season the pork chops with salt and black pepper to taste. Set aside.
Cut the stems from the greens and discard. Fill a large bowl with water and fully plunge the leaves and agitate gently. Lift the greens from the water and place in a colander.
Empty the water from the bowl and repeat to ensure ensure that all sand is washed from the greens. Do not shake away the excess water.
Cut the greens crosswise into wide ribbons (about 2 1/2 inches).
Heat olive oil in a large skillet over medium, add garlic and cook, stirring for 1 minute.
Add greens and crushed red pepper and continue to cook, stirring occasionally, until wilted and the excess moisture is evaporated and the greens are tender, 8 to 10 minutes.
Transfer to a serving dish and keep warm.
Heat the remaining 2 teaspoons olive oil in a large nonstick pan over medium-high heat.
Add pork chops and cook until the bottom is side is golden brown, about 3 minutes.
Flip chops and reduce heat to medium and continue to cook until done (145°F), about 6 more minutes.
Transfer to a plate and keep warm.
Reduce pan heat to medium-low and add pears in a single layer.
Cook until golden, turning once, about 2 minutes per side. add orange juice, 3 tablespoons water and sage.
Stir to loosen the any browned bits from the pan bottom. Add pork chops and any accumulated juices from the plate back to the pan and let cook for 1 minute before removing from the heat.
Serve pork chops topped with pears and pan juices and alongside the greens.