- 6 large tomatoes (about 3 pounds), coarsely chopped
- 1 medium green bell pepper (about 6 ounces), cored, seeded, deveined, and coarsely chopped
- 1 medium yellow onion (about 8 ounces), coarsely chopped
- 8 garlic cloves, peeled
- 20 Caribbean sweet peppers (ajíes dulces), seeded and cut in half
- 1/2 cup tomato sauce
- 1/4 cup coarsely chopped cilantro
- 2 broad-leaf culantro leaves
- 1 1/2 tablespoons cider vinegar
- 1 teaspoon dried oregano
- 1/4 cup achiote-infused extra-virgin olive oil
- 8 ounces slab bacon, rind removed, cut into 1/4-inch dice
- 1 1/2 pounds boneless pork shoulder or butt, cut into 1/2-inch dice
- 1/4 cup chicken broth
- 1/3 cup whole milk
- 1 1/2 pounds malanga, peeled and cut into 1-inch cubes
- 1 1/2 pounds green bananas, peeled and thickly sliced
- 1/2 green plantain, peeled (see Cooks' notes) and thickly sliced
- 8 ounces calabaza (West Indian pumpkin) or Hubbard or kabocha squash, peeled, seeded, and cut into 1-inch cubes
- 1/4 cup achiote-infused extra-virgin olive oil
- 1/2 to 1 teaspoon salt, or to taste
- Twenty-five 12-inch plantain leaf squares (4 to 5 packages; see Cooks' notes for how to prepare)
- 1/4 cup achiote-infused extra-virgin olive oil
- Twenty-five 42-inch pieces of kitchen twine
- 1/3 cup dark raisins
- One 15-ounce can chickpeas, drained and rinsed, or 2 cups cooked chickpeas
- 2 medium red bell peppers (about 6 ounces), roasted (see Cooks' notes), peeled, cored, seeded, and cut into 1/4-inch-wide strips
- 50 pimiento-stuffed olives, cut in half
- Place all the ingredients in a blender or food processor and puree. Set aside. DO AHEAD: You can make the seasoning base (recado) the day before.
- Heat the oil in a 12-inch skillet over medium heat. Add the bacon and brown for 2 to 3 minutes. Add the pork and cook, stirring, until it begins to release its fat, about 15 minutes.
- Stir in the recado, reduce the heat to low, and cook, covered, for about 50 minutes, or until the pork is tender when pierced with the tip of a sharp knife. Add some chicken broth if the sauce thickens too much during cooking. When the meat is done, transfer it to a plate with a slotted spoon. Set the sauce aside. DO AHEAD: You can make the sofrito the day before.
- Working in 2 or 3 batches, puree the milk, malanga, green bananas, green plantain, and calabaza in a blender or food processor and pour into a large bowl. Add the oil and salt and mix well to color the masa evenly. Stir in the reserved sauce. Taste for seasoning and set aside.
- Place one plantain leaf square on a work surface with the veins perpendicular to you. Brush generously with achiote oil. Place 3 heaping tablespoons of masa in the center of the leaf and spread into a 6-inch square, leaving a 3-inch margin on all sides. Place 3 tablespoons of the diced pork on top, forming a rectangle. Garnish with 4 raisins, 4 chickpeas, a strip of red pepper, and 4 olive halves. Tie the tamal following the instructions for the pastel wrap (see Cooks' notes). Repeat with the remaining wrappers and ingredients. DO AHEAD: You can prepare the plantain leaves the day before.
- Using two steamers (or working in batches), steam for about 1 hour (see Cooks' notes).