Preheat oven to 400°F (200°C). Line a baking sheet with parchment paper. Season medallions with pepper. Heat oil in a skillet over medium-high heat, add medallions and cook, turning once, until browned, about 2 to 3 min. per side. Place medallions on a plate and let cool in refrigerator.
In the same skillet, melt 2 tsp (10 mL) butter, add leeks and onions and cook until softened, about 5 min. Add prosciutto and cook until tender, about 5 min. Add wine and cream, simmer until liquid evaporates. Remove from heat, let cool slightly and then mix in Parmesan and foie gras. Set aside.
Lay a sheet of phyllo on work surface and brush with melted butter. Repeat with remaining phyllo to create a layered crust. Cut into 4 equal rectangles. Place 1/4 cup (60 mL) of the foie gras mixture in the centre of rectangle and top each with a medallion. Fold one corner of pastry up onto top of medallion. This creates a natural crease. Fold crease up towards top of medallion. Repeat until foie gras and medallion is completely enclosed. Brush packet with melted butter and pinch together any loose ends to seal. Place, seam-side up, on prepared baking sheet. Repeat with remaining phyllo.
Bake until a meat thermometer reads 145°F (63°C), about 12 to 15 min. Remove Wellingtons from oven and let rest 5 min. before serving with Creamy Pear Sauce.
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