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Preheat oven to 180°C (350°F).
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In a small bowl, mix together pesto and garlic, then set aside. In an ovenproof skillet, heat oil over medium-high heat. Season pork tenderloins with pepper to taste. Sear 1 to 2 minutes each side, one tenderloin at a time if necessary. Set skillet aside.
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Place pork tenderloins on clean work surface and brush all over with pesto mixture. Set aside. Place four slices of prosciutto, overlapping, on a clean surface and place eight basil leaves on top. Place one pork tenderloin along the edge then roll up tightly.
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Repeat same steps with second tenderloin. Pour off any excess oil before placing tenderloins in skillet. Bake in oven for 15 minutes or until meat is pinkish inside and an instant-read thermometer inserted in centre of tenderloins reads 70°C (160°F) and prosciutto is crispy.
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Cover tenderloins with foil and let stand for 5 minutes. Slice pork tenderloins and serve with rapini and orzo or risotto with fresh herbs.
VARIATION : Replace prosciutto with pancetta and sprinkle basil leaves with 60 mL (1/4 cup) crumbled goat cheese.