Heat 1 Tbsp. oil in a large pot over high. Cook ground beef, breaking up with a spoon, until browned but not completely cooked through, 6–8 minutes. Transfer to a medium bowl with a slotted spoon, leaving as much fat in pan as possible.
Reduce heat to medium and cook onions, chopped, red bell peppers, seeded, chopped, and remaining 1 Tbsp. oil, stirring, until tender but not browned, 6–8 minutes; season with salt and black pepper. Add ground cumin, sweet paprika, dried oregano, and cayenne pepper and cook, stirring, until fragrant, about 1 minute. Add low-sodium chicken stock or broth and reserved beef along with any accumulated juices to pot. Stir in sugar, salt, and black pepper. Bring to a simmer and cook, stirring and scraping up any brown bits, until most of the liquid is evaporated, 15–20 minutes; taste and season with salt and black pepper, if needed. Stir in raisins. Transfer to a medium bowl, cover, and chill at least 3 hours.
Preheat oven to 375°.
Roll the pie crust to 1/4-inch thickness. Cut dough into 5-inch circles. Place 2 Tbsp. filling in the center of each round.
Top with 2 olive halves. Brush water around half of outer edge of each round. Pinch edges to seal.
Using a fork, crimp edges. Transfer empanada to a parchment-lined sheet tray, spacing 1" apart. Repeat with remaining rounds.
Bake empanadas until golden brown and slightly darker around the edges, 25–35 minutes.
1 pound (3 1/4 cups) all purpose flour
1/2 pound (11/2 cups) shortening
1 teaspoon light brown sugar
1 teaspoon salt
1 teaspoon white vinegar
1 beaten egg
4 tablespoons cold water
In a large bowl, mix together flour, and shortening.
In a small bowl, combine the sugar, salt, vinegar, egg, and water.
Blend all ingredients to form a ball. Add more water if necessary.
Chill dough and use as needed.