Place the BButternut Squash (12 ounce) in a medium saucepan and cover with cold water. Bring to a boil and then lower to a simmer. Cook for approximately 10 minutes until fork tender.
Strain squash, add back to pot and add half of the Butter (2 tablespoon). Mash with a potato masher. Season with half a teaspoon of Sea Salt (1/2 teaspoon) and Ground Black Pepper (1/4 teaspoon). Cover and hold.
Trim Asparagus (8 ounce) by snapping the thicker ends where they break naturally. Discard woody ends. Slice the asparagus in half on a bias cut. Pat Turkey Cutlets (4) dry with a paper towel and season with Sea Salt (1/4 teaspoon) and Ground Black Pepper (1/4 teaspoon).
Evenly distribute Fresh Sage (0.25 ounce) leaves on top of each cutlet, approximately 2 per, and place 1 slice of Prosciutto (1 package) on top. Press the prosciutto into the turkey to make the sage and prosciutto stick.
Heat Olive Oil (1 tablespoon) and half of the remaining Butter (1 tablespoon) in a large saute pan over medium-high heat. When butter is melted, add turkey cutlets with the prosciutto face down and cook for 2 minutes.
Turn over and cook for another 2 minutes. Transfer cutlets to a plate and cover with foil to keep warm. Keep pan over heat for next step.
After removing cutlets from the pan, with the pan still hot, add the Port Cooking Wine (1/2 cup). Cook until the steam disappears and wine is reduced by half. Stir in remaining Butter (1 tablespoon). Remove from heat and hold for plating, being careful not to over reduce or burn the sauce!
Heat Olive Oil (2 teaspoon) in a medium saute pan over medium-high heat. Add Garlic (2 clove) and saute for 1 minute or until golden brown.
Add asparagus, Sea Salt (1/4 teaspoon) and a pinch of black pepper. Cook for approximately 4 minutes until asparagus is tender but still has a bite.
Add any drippings from turkey to the sauce. If sauce becomes too loose, heat again and stir to tighten. Remove from heat. Evenly distribute the butternut squash mash between two dishes toward the bottom of plate. Using a spoon, spread it across the plate.
Lay two cutlets over the squash side by side, slightly overlapping. Plate the asparagus behind the turkey by stacking them with height. Drizzle port reduction over the cutlets.