1 cup plus 3 tbsp. canola oil
1 1-lb. piece boneless pork shoulder
Kosher salt, to taste
4 plum tomatoes, cored and roughly chopped
3 cloves garlic, roughly chopped
2 ancho chiles, stemmed, seeded, and roughly
1 small white onion, roughly chopped
1 tsp. distilled white vinegar
1 tsp. sugar
13 14" x 14" pieces fresh or frozen
and thawed banana leaf,
trimmed of hard edges, rinsed, and patted dry
1 tsp. achiote paste (ground annatto seed and
2 cups masa harina (corn flour for tamales;
preferably Maseca brand)
1 cup rice flour
1⁄4 cup capers, rinsed
15-20 large pitted green olives
1⁄2 red bell pepper, cored, seeded, and
1. Heat 2 tbsp. oil in a skillet over medium-high heat. Season pork with salt; cook, turning occasionally, until browned, 10–12 minutes. Remove from heat and let cool. Cut pork into 3"–4"-long slices about 1⁄2" thick and set aside.
2. To make the chile sauce: Purée tomatoes, garlic, chiles, onions, and 1⁄4 cup water in a blender. Heat 1 tbsp. oil in a saucepan over medium-high heat. Slowly add purée, vinegar, sugar, and salt; boil. Reduce heat to medium-low; simmer, stirring occasionally, until thick, about 40 minutes. Set sauce aside.
3. Heat a skillet over medium-high heat. Toast 10 banana leaf pieces in skillet, one at a time, turning once, 20–30 seconds. Transfer to a plate. Alternately layer banana leaves, dull side up, with 14" squares of foil; trim protruding leaves.
4. To make the corn-flour dough: Put achiote paste and 1 quart warm water into a bowl. Mash paste with your fingers to dissolve. Add masa harina, rice flour, remaining oil, and 2 tbsp. salt; whisk. Transfer mixture to a medium pot; cook over medium-high heat, whisking constantly, until dough is very thick and pulls away from sides of pot, 6–8 minutes. Transfer dough to a bowl.
5. To assemble the tamales: Place about 1⁄2 cup dough into middle of a banana leaf; form dough into a 4" square. Top with 2 pieces pork, 4–5 capers, 1–2 olives, 2 slices bell pepper, and about 2 tbsp. chile sauce. Fold sides of banana leaf over filling to make a snug rectangular package. Repeat process with remaining dough, pork, capers, olives, peppers, and a little chile sauce to make 10 tamales in all. (Reserve remaining chile sauce for another use.)
6. Place a large collapsible steamer inside a deep wide pot; pour in enough water for a depth of 1". Line steamer with the 3 remaining banana leaf pieces. Arrange tamales in steamer, standing them upright. Cover pot; boil. Reduce heat to medium and steam tamales, covered, until firm and cooked through, 45–50 minutes. Unwrap; serve tamales hot or at room temperature.