In a large skillet or sauté pan, heat 1/4 cup of olive oil over medium heat. Add the cubed potatoes and cook, stirring occasionally, until golden brown and slightly crispy on the edges (about 7-10 minutes). Remove the potatoes with a slotted spoon and set aside on a paper towel-lined plate to drain excess oil.
Add the ground beef to the same skillet set over medium-high heat. Breaking it up with a wooden spoon, cook it until it's browned and no longer pink (about 5-7 minutes). Remove the beef and set aside. Drain any excess fat, leaving just 1-2 tablespoons in the pan.
Reduce the heat to medium and add the diced onion, red bell pepper, and yellow bell pepper. Stir and cook until softened (about 6 minutes).
Add the minced garlic, oregano, salt, black pepper, and cumin powder, stirring for 30 seconds until fragrant.
Return the browned beef to the pan and stir in the tomato sauce, beef broth, and dry white wine. Bring to a simmer, add the bay leaf, and reduce the heat to low. Simmer uncovered for 10 minutes (or longer), stirring occasionally.
Add the fried potatoes, green olives, raisins, and capers, and mix well. Continue to simmer for an additional 5-7 minutes, allowing the flavors to develop.
Season to taste with salt and black pepper, and remove the bay leaf. Serve over white rice with sweet plantains or warm tortillas. Enjoy!