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Chop the lacy leaves off of the fennel. Set aside. Chop the bulb into small pieces.
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Heat the olive oil in a large skillet.
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Add the fennel and sauté until the fennel softened and starts to caramelize.
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Stir in the garlic, cooking for one minute. Mix in the tomato paste.
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Add the chopped cherry tomatoes and sauté for a few minutes until they soften.
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Season with salt and freshly ground black pepper.
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Mix in the wine, strained tomatoes, and the bay leaf.
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Add the peeled tomatoes and break them up with a spoon. Stir to combine everything.
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Bring to a boil, lower the heat, cover and simmer for 15 minutes. Remove the bay leaf.
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Use a stick blender to puree the mixture. Alternately, transfer to a food processor working in batches, if necessary, and puree.
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At this point, you can transfer the mixture to a pot or return it to the pan.
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Over medium heat, stir in the cream.
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Add the sugar and season with sugar, salt, and freshly ground pepper to taste.
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Cook for another 10 minutes. Season again to taste.
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Remove from heat, garnish with the fennel leaves and serve.