Bring 1 cup water to a boil and pour over the dried cherries in a small bowl. Steep the cherries until plump and soft, about 20 minutes. Puree the water, cherries and tomatoes in a blender and reserve.
Sprinkle the beef cubes with salt and pepper. Heat the oil a large heavy-bottomed pot or Dutch oven over medium-high heat. Add the beef, in two batches, stirring occasionally, until browned, about 7 minutes per batch. Remove the beef to a plate.
Reduce the heat to medium, add the onions and peppers and cook, stirring, until the vegetables begin to soften, about 3 minutes. Add the chili powder and oregano, stirring until fragrant, about 30 seconds. Pour in the tomato-cherry sauce, the soy sauce, chipotle and 2 cups water. Return the beef to the pot and simmer the chili until the meat is tender, about 3 1/2 hours, adding water if necessary to keep the beef submerged.
Add the black beans and bean liquid to the chili during the last 30 minutes of cooking. Serve with rice and sprinkle with Cheddar.
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