Like most homestyle comfort foods, there are a million and one ways to make picadillo. Some call for oven roasted tomatoes, some call for a sofrito base, some add capers or chili powder. I've adapted this picadillo recipe from several variations over the years into a fast and kid-friendly weeknight dinner that my family loves. I keep the prep time low by blending a spicy tomato sauce using canned fire-roasted tomatoes. They're a quick way to add depth and flavor without any extra work.
Place the onion, tomatoes, jalapeno, garlic, and apple cider vinegar in a blender. Blend on high until pulverized and smooth.
Heat a dutch oven over medium high heat. Add the olive oil and heat until shimmering. Add the beef and cook until no longer pink, breaking into small pieces with a wooden spoon, 4-5 minuets.
Add the raisins, tomato paste, cumin, oregano, salt, and pepper. Stir until the tomato paste and seasonings are incorporated into the beef.
Pour in the tomato puree, add the bay leaf, and stir. Cover, reduce heat to medium and simmer 20 minutes, stirring occasionally to prevent the bottom of the pot from scorching.
Stir in the olives and 1-2 tbsp olive brine. Simmer until the olives are heated through, 2-3 additional minutes.
Serve over rice or cauliflower rice and garnish with fresh chopped cilantro.