Heat oil in a large skillet over medium-high heat. Add onion, garlic, and bay leaves and saute until onion is soft, stirring frequently, about 4 minutes.
Add ground beef to skillet and cook until browned. Once the meat is browned, carefully away from the flame, tilt pan and remove excess fat with a large spoon.
Add the white wine and stir for another minute. Then add the chopped cherry tomatoes, tomato paste, pimento stuffed Spanish olives, raisins, dried oregano, cumin and cayenne pepper. Simmer over low heat for another 8 minutes, stirring occasionally. Season with salt and pepper.
As a filling for empanadas or tacos
Over white rice with fried plantains or black beans
With a side salad and black beans
To make Picadillo soupier for serving over rice, add additional wine, chicken or beef stock.