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To make the pumpkin seed filling: Heat a large skillet over medium heat.
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Add the pumpkin seeds.
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Cook, stirring and shaking the pan, until fragrant and slightly golden, about 4 minutes.
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They will pop as they cook, so stand back.
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Transfer toasted pumpkin seeds to a food processor to cool slightly.
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In the same skillet, heat the olive oil over medium-low heat.
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Add the garlic and saute until softened, about 4 minutes.
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Stir in the jalapenos and cook another minute.
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Stir in the chicken broth, turn heat to medium, and cook for another 3 minutes, until the stock is slightly reduced and the jalapenos are softened.
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Add the mixture to the pumpkin seeds in the processor.
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Blend until the mixture is a coarse but spreadable paste.
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Place in a medium bowl and cool while you prepare the butternut sauce.
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To make the butternut sauce: Wash leeks thoroughly and then thinly slice the white and pale green parts only.
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Peel the butternut squash.
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Cut it in half, and scoop out and discard seeds and stringy flesh.
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Cut the squash into 3/4-inch pieces.
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In a large skillet, heat the olive oil over medium heat.
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Add the leek and saute until soft, about 3 minutes.
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Add the squash and chicken broth, increase the heat to high, and bring to a boil.
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When it reaches a boil, reduce the heat to a low simmer, cover, and cook until the squash is tender, 10 to 15 minutes.
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Transfer to a blender.
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Add the cumin, salt, and whipping cream.
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Puree until the sauce is completely smooth.
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Return to the skillet.
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If the sauce is too thick (possibly because you started with too heavy a squash), thin with a bit more chicken broth.
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To make the chicken breasts: Lay each breast flat and pound until 1/8 to 1/4 inch thick.
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Spread 1/4 of the pumpkin seed filling across each breast.
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Sprinkle 1/4 of the Dry Jack cheese over the filling.
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Fold each breast in half, short-end to short-end, to create a pocket.
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Heat the olive oil and butter over medium heat.
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Place the flour in a shallow bowl and carefully dredge each chicken pocket in the flour.
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Add to the pan, one by one.
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Cook until all pink is gone, about 5 minutes per side.
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In the meantime, gently reheat the squash sauce.
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Divide the rice among 4 plates, top each with a stuffed chicken breast.
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Spoon the butternut sauce over all.