Guacamole Enchiladas with Guajillo-Tomatillo Beef Sauce

From: Chef Roberto Santibanez, Fonda, New York City. Yield: 12 enchiladas.

1 lb. tomatillos (10 to 12), husked and rinsed
3 oz. guajillo chiles (12), wiped clean, stemmed, slit open, seeded and deveined
4 cups water, or more if necessary
2 large garlic cloves, peeled
¼ tsp. aniseed
¼ teaspoon dried oregano, preferably Mexican
1 tsp. fine salt, or 2 tsp. kosher salt
2 Tbsp. mild olive oil
1¼  lb. beef sirloin or chuck, excess fat removed and meat finely chopped, or 1 lb. ground beef
12 corn tortillas
1¾  cup guacamole (recipe follows)
¼ cup vegetable oil

Classic Guacamole:
2 Tbsp. finely chopped white onion
1 Tbsp. minced fresh Serrano or jalapeno chile, including seeds, or more to taste
½ tsp. kosher salt, or ¼  teaspoon fine salt
¼ cup chopped cilantro, divided
1large or 2 small ripe Mexican Hass avocados, halved and pitted
as desired, a squeeze of lime
 
For guacamole: Mash the onion, chile, salt (the coarseness of kosher salt helps you make the paste), and half of the cilantro to a paste in a molcajete or other mortar. You can also mince and mash the ingredients together on a cutting board with a large knife or a fork, and then transfer the paste to a bowl.

Score flesh in avocado halves in a crosshatch pattern (not through the skin) with a knife and then scoop it with a spoon into mortar or bowl. Toss well, then add the rest of the cilantro and mash coarsely with a pestle or a fork. Season to taste with lime juice (if you’d like) and additional chile and salt.

For enchiladas: Put tomatillos and chiles in a 3- to 4-quart heavy saucepan or pot, add 4 cups of water (or more to cover the tomatillos), and bring water to a simmer over medium-high heat. Lower heat and simmer gently, turning tomatillos and chiles occasionally, until tomatillos have turned a khaki-green color and are tender, but still intact, about 15 minutes. If necessary, let tomatillos stand in the pan off the heat for up to 15 minutes longer, or until they are fully cooked through. Gently drain tomatillos and chile in a sieve set over a large bowl, being careful to keep the tomatillos intact and reserving the cooking liquid.

Transfer tomatillos and chiles to the blender jar. Add the garlic, aniseed, oregano and salt and blend until smooth, adding a little of the reserved cooking liquid if necessary to help blend. Be careful when you’re blending hot ingredients: Cover the top with a kitchen towel and hold the top firmly in place with your hand. Work in batches to avoid blending with a full jar. Strain sauce through a medium-mesh sieve and into a bowl.

Wipe the saucepan clean, and heat olive oil in the saucepan over medium-high heat until it shimmers. Carefully pour sauce into the oil (it may splatter), and let the sauce simmer, stirring often, until it has thickened slightly, 5 to 7 minutes. To avoid making a mess of your stove, use a splatter screen to partially cover the pot.

Add the rest of the reserved cooking liquid and return sauce to a boil. Add the beef, stirring to break up the meat (a sturdy whisk is great for this), and simmer vigorously, stirring occasionally, until the sauce is just thick enough to coat the meat (like a thick Bolognese sauce or Sloppy Joe mixture), about 15 minutes. Season to taste with additional salt, and keep the sauce warm.

Heat vegetable oil in a small skillet just large enough to fit a tortilla over medium heat until it shimmers. Put a tortilla in the oil (the oil should be hot enough so that it sizzles around the edges of the tortilla) for 8 to 12 seconds, then carefully turn the tortilla over with tongs and cook until the other side bubbles but the tortilla is still soft, 8 to 12 seconds more. With tongs, transfer tortilla to paper towels, and blot on both sides. Repeat procedure with remaining tortillas, adding more oil and using more towels as necessary and stacking the tortillas on the plate once they are blotted. Fill tortillas using 2 Tbsp. guacamole for each tortilla. Roll it up and transfer it, seam-side down, to a serving dish.

To serve, divide rolled, filled tortillas among 4 plates. Spoon the meat sauce generously over them. Serve immediately.