Picadillo (Ground Beef):
In a large skillet, heat 2 tablespoons of olive oil over medium heat and cook the onion and bell pepper until soft (about 4-5 minutes). Add the garlic and cook for 20-30 seconds. Mix in the ground beef and stir. Add bay leaf, cumin, salt, and pepper; drain off excess grease. Return meat to pan.
Add the tomato sauce, sugar, and wine. Cover and continue cooking over medium-low heat (about 20 minutes), stirring occasionally. If the sauce thickens too much, you can add a little bit of water.
Add capers and olives and mix well. Taste and adjust any salt and pepper, if needed. Remove from heat.
Place picadillo into an oven-proof baking pan. Transfer the entire pan to the refrigerator and chill 2-3 hours or place in the freezer for 30 minutes.
Sweet Plantain Mash:
Bring water to a boil (filled a third of the way up) in a large saucepan over medium-high heat. Trim each end from plantain and cut in half. Add plantains, 1 teaspoon salt, and juice from ½ a lime to boiling water; cover and cook until tender, about 25-30 minutes.
Drain plantains thoroughly (reserving ½ cup water) and steam dry 5-10 minutes.
In the same pan used to cook the plantains, heat oil on low heat. Add garlic and infused oil 1½ – 2 minutes, making sure garlic does not brown. Set aside until ready to use.
Peel the skin off when cool enough to handle and add plantains to the pan with the infused garlic. Mash to desired consistency, add remaining lime juice, ½ teaspoon salt, black pepper, and reserved water; mix until combined.
To Assemble Pie:
Preheat oven to 350F.
Remove pan from freezer. Sprinkle fresh cilantro over the picadillo, and spread sweet plantain mash over the meat and cilantro. Use a fork to rake over the surface. Sprinkle with parmesan, drizzle with butter. Bake for 30 minutes. Let rest for 5 minutes before serving. Enjoy!
