In a medium pot, heat 1/4 cup of the oil over medium heat. Add the onion
and cook, stirring, until soft and golden brown, about 7 minutes.
Add the garlic and cook, stirring, until fragrant, about 30 seconds. Stir
in the red pepper. Add the tomato paste and cook, stirring frequently, about
1 minute. Stir in the brown sugar. Pour in the coffee, vinegar, and tomatoes;
bring to a boil; and then lower to a simmer. Simmer 10 minutes. Set aside to
Working in small batches, transfer the tomato-coffee mixture to a blender
and puree. Season with salt and pepper to taste. Set aside.
Heat the oven to 275 degrees F.
Season the brisket with salt and pepper. In a Dutch oven with a tight-fitting
lid, heat the remaining 1/2 cup oil. Brown the brisket on both sides. Drain
off the oil, leaving the brisket in the Dutch oven. Turn the brisket so that
the fat side is facing up and then coat it with the pureed tomato-coffee mixture.
Cover the Dutch oven and place it in the oven. Bake for 3 hours, basting frequently.
Remove the lid and bake uncovered until the brisket is glazed and very tender,
about an hour and a half more.
Remove the brisket and set it aside to rest for 10 minutes, covered with
foil, before slicing thinly across the grain.