Chicken and Green Olive Enchiladas

READY IN: 3hrs 30mins




  • Place chicken and broth in heavy large pot. Bring to a boil.
  • Reduce heat to medium-low, partially cover pot and simmer until chicken is cooked, about 30 minutes.
  • Cool chicken in broth.
  • Strain broth and spoon off fat; reserve broth.
  • Remove chicken skin and bones; discard.
  • Shred chicken coarsely; transfer to a large bowl. Set aside.
  • Heat 3 Tbl oil in a large saucepan over medium-low heat.
  • Add 1 cup onion, garlic, oregano, cumin and cinnamon to the saucepan. Cook until onion is almost tender, stirring occasionally, about 10 minutes.
  • Mix in chili powder and flour; stir 3 minutes.
  • Gradually whisk in 4.5 cups of the broth (reserve remaining broth for Red Rice).
  • Increase heat to medium-high and bring to a boil.
  • Boil until reduced to about 3 cups, stirring occasionally, about 35 minutes.
  • Remove from heat and whisk in chocolate. Season with salt and pepper, cool.
  • Heat 1 Tbl oil in medium skillet over medium heat.
  • Add 1 tortilla and cook until just pliable, about 20 seconds per side.
  • Transfer to a paper-towel-lined baking sheet. Repeat with remaining tortillas, adding oil as needed.
  • Spread 1/3 cup of sauce in each of two 13x9x2 -inch glass baking dishes.
  • Mix 1 cup of the sauce into the chicken.
  • Arrange 8 tortillas on work surface.
  • Spoon 3 Tbl cheese, 1 Tbl olives, 1 Tbl onions, and 1/4 cup chicken over center of each tortilla.
  • Roll up tortillas. Arrange seam side down in 1 prepared dish.
  • Repeat with remaining tortillas (can be prepared 1 day ahead. Cover sauce and enchiladas separately, cool).
  • Pre-heat oven to 375 degrees F. Top each enchilada with remaining sauce, then sprinkle with remaining cheese.
  • Cover with foil; bake for 20 minutes (30 minutes if chilled.).
  • Remove foil and bake until sauce and cheese bubbles, about 10 minutes.
  • Let stand 10 minutes and serve.