In Venezuela's capital city, Caracas, large cuts of beef are roasted in a rich caramel sauce whose sweetness is tempered by vinegar. The result is beef cloaked in a sauce as dark as an ink pot bobbing in the middle of the ocean on a moonless night. Our version captures the traditional essence with a flavorful reduction of red wine, demi-glace, and Worcestershire sauce. We serve it with the classic accompaniment of twice-fried plantain chips for a delicious mixture of new and familiar flavors.
Mince garlic. Peel plantain and cut into ½” slices. Trim zucchini ends and cut on an angle into ¼" slices. Trim and quarter radishes. Peel and halve shallot. Slice half the shallot into thin strips (julienne) and cut other half into a fine dice. Rinse steaks, pat dry, and season both sides with ½ tsp. salt and a pinch of pepper.
Begin Tostones and Sear Steak
Line a plate with a paper towel. Heat 2 Tbsp. olive oil in a medium non-stick pan over medium heat. Add plantains to hot pan and cook 3-4 minutes per side, or until lightly browned. Remove to towel-lined plate and let cool. Drain all but 2 tsp. oil from pan and place over medium-high heat. Add steaks to hot pan and cook 2 minutes per side, or until browned. Transfer steaks to a plate. No need to wipe pan clean.
Finish Steaks and Cook Vegetables
Place zucchini, radishes, and julienned shallots on one half of prepared baking sheet. Toss with 2 tsp. olive oil and a pinch of salt and pepper. Spread into a single layer and bake 15 minutes. Remove from oven and place steaks on other half of baking sheet. Bake 2-4 minutes, or until steaks reach a minimum internal temperature of 145 degrees and vegetables are tender and lightly charred.
Finish the Tostones
While vegetables are cooking, replace paper towels on plate. Lay plantain slices on a clean surface and smash to ¼” thickness with bottom of a clean pan. Place pan used to cook steaks over medium heat, replenishing olive oil if necessary. Return plantains to hot pan and cook 4 minutes per side, or until golden brown. Transfer to towel-lined plate and season with a pinch of salt and pepper.
Make the Sauce
Heat 1 tsp. olive oil in a small pan over medium-high heat. Add garlic, oregano, and finely diced shallots. Cook 30 seconds, or until fragrant. Add red wine and cook 2-4 minutes, or until mostly evaporated. Add demi-glace, Worcestershire sauce, and ¼ cup water. Return to a simmer and cook 30 seconds, or until sauce thickens slightly. Remove pan from burner and swirl in butter. Season with a pinch of salt and pepper.
Plate the Dish
Place vegetables and tostones on a plate. Pool sauce in front of vegetables and serve steak in sauce.