Heat 1 tablespoon olive oil in a large skillet over medium-high heat for 1 minute. Add ground beef and cook 4-5 minutes, breaking it up with a wooden spoon, until no pink remains and beef is deeply browned. Transfer to a plate.
1 lb ground beef, 2 Tbsp olive oil
Add remaining 1 tablespoon olive oil to the same skillet. Add diced onion and green bell pepper, cook 5 minutes over medium heat, stirring occasionally, until softened and translucent. Add minced garlic, cook 1 minute until fragrant.
1 medium onion, 1 medium green bell pepper, 4 cloves garlic, 2 Tbsp olive oil
Return browned beef to the skillet. Stir in tomato sauce, cumin, bay leaf, salt, and pepper. Add green olives and raisins, stir to combine.
1 lb ground beef, 1 cup tomato sauce, 1 tsp ground cumin, 1 leaf bay leaf, 0.25 cup green olives, 2 Tbsp raisins
Bring mixture to a simmer, then reduce heat to medium-low. Cook uncovered 10-15 minutes, stirring every 3-4 minutes, until sauce thickens and coats the beef. The mixture should look glossy and slightly reduced, not watery.
1 lb ground beef, 1 cup tomato sauce, 1 tsp ground cumin, 1 leaf bay leaf, 0.25 cup green olives, 2 Tbsp raisins
Remove from heat, discard bay leaf. Let Picadillo sit 5 minutes off heat so flavors meld and sauce thickens further. Taste and adjust salt or add a splash of vinegar if it tastes too sweet.
1 leaf bay leaf
