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1
Place beans and soaking water in a large, heavy pot.
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2
Add halved onion and bring to a gentle boil.
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3
Skim off any foam that rises, then add crushed garlic and bay leaf, reduce heat, cover and simmer 30 minutes.
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4
Add salt and continue to simmer another 45 minutes to an hour.
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5
Using tongs or a slotted spoon, remove and discard onion and bay leaf.
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6
.
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7
Meanwhile, heat oil over medium heat in a heavy skillet and add chopped onion.
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8
Cook, stirring often, until tender, about 5 minutes.
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9
Add a generous pinch of salt, stir in chopped garlic, stir together for 30 seconds to a minute, until fragrant, and add ground chili and cumin.
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10
Cook, stirring, for 2 to 3 minutes, until mixture begins to stick to pan.
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11
Add chopped tomatoes with juice, pinch of sugar, and salt to taste.
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12
Bring to a simmer and cook, stirring often, until tomatoes have cooked down and mixture is beginning to stick to the pan, about 10 minutes.
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13
Stir in tomato paste dissolved in water and bring back to a simmer.
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14
Simmer, stirring often, for 10 minutes, until mixture is thick and fragrant.
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15
Stir tomato mixture into beans.
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16
Add winter squash and bring to a simmer.
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17
Taste and adjust salt.
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18
Simmer, stirring often so that the chili mixture doesnt settle and stick to the bottom of the pot, for 45 minutes.
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19
Add more water if chili seems too thick.
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20
Stir in corn and simmer for another 10 minutes.
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21
The beans should be very soft and the chili thick and fragrant.
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22
Taste and adjust seasonings.
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23
Shortly before serving stir in cilantro.
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24
Simmer for 5 minutes.
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25
Spoon into bowls.
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26
If you wish, top with grated cheddar, Monterey jack, or crumbled queso fresco.
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27
Serve with biscuits or cornbread.
