Place a large pot or Dutch oven with a tight-fitting lid over medium-high heat.
Add the oil.
Once hot, add the chopped onions and cook, stirring occasionally, until soft, about 5 minutes.
Stir in the minced garlic and cook for one more minute until fragrant.
Add the chopped tomatoes, espresso, chili powder, brown sugar, cinnamon stick, and dried black beans.
Pour in enough water to cover all the .
Bring the mixture to a boil, then reduce the heat to a steady simmer.
Cover the pot and cook, stirring occasionally, for 30 to 40 minutes, or until the beans begin to soften.
Add a generous pinch of salt and pepper.
Continue to cook, covered, until the beans are fully tender, which can take another 45 minutes to 1. 5 hours.
Once the beans are tender, taste the chili and adjust the seasoning as needed, adding more sugar, salt, or pepper to your liking.
Remove the cinnamon stick before serving.