- 8 dried guajillo chiles, seeded
- 4 large garlic cloves
- 2 teaspoons dried oregano
- 6 tablespoons canola oil, plus more for brushing
- Salt and freshly ground pepper
- 1 trimmed hanger steak (about 1 pound), cut into 4 pieces
- 1 large onion, finely chopped
- 1/4 cup light brown sugar
- 1/4 cup cider vinegar
- In a medium microwave-safe bowl, cover the chiles with water and microwave at high power until softened, 5 minutes. Let cool slightly. Transfer the chiles and 1/2 cup of the soaking liquid to a blender. Add the garlic, oregano and 4 tablespoons of the canola oil; puree until very smooth. Strain the puree and season with salt and pepper.
- Season the steaks with salt and pepper and rub with half of the chile puree. Transfer the steaks to a resealable plastic bag and refrigerate overnight.
- In a medium saucepan, heat the remaining 2 tablespoons of oil. Add the onion and cook over moderate heat until softened, about 7 minutes. Add the remaining chile puree and cook, stirring, for 2 minutes. Add the brown sugar and vinegar and simmer for 3 minutes. Season the glaze with salt and pepper.
- Light a grill or preheat a grill pan. Brush the steaks with oil and grill over moderate heat until medium-rare, 12 minutes; brush with 3 tablespoons of the glaze in the last 2 minutes. Let the steaks rest for 5 minutes before slicing 1/2 inch thick. Serve the steaks with the remaining chile glaze.
A rich, peppery Zinfandel.