Step 1: Preheat the oven to 350F.
Step 2: Make the Pesto - toast 1/2 cup of pine nuts , on a cookie sheet, at 350F for 5-8 minutes until fragrant, then set aside to cool- In a food processor, combine the 1/4 cup of the toasted nuts, basil leaves, spinach, Parmesan, salt/pepper and garlic, then add the olive oil- set the pesto aside.
Step 3: Increase the oven temperature to 425F.
Step 4: Make the stuffing - in a saucepan, heat the vegetable oil over medium, add the spinach and saute until wilted, add the garlic and shallots- saute for a minute more then set aside.
Step 5: Stuff the chicken - cut a pocket into each breast, stuff each breast with 1/4 of the stuffing mixture, 1 Tablespoon of pesto and 1/8 cup Parmesan - season with salt, pepper and oregano.
Step 6: In a large bowl, place the asparagus, 1 Tablespoon olive oil, 1 clove chopped garlic and season with paprika, salt, pepper and oregano - toss to coat well and set aside.
Step 7: Heat , over med-high, 3 Tablespoons olive oil in a large, deep and oven proof skillet, until very hot and there are wisps of smoke, place the chicken ( skin side down if the skin was left on) in the hot skillet and brown well ( to make crispy) for a few minutes on each side.
Step 8: Place the asparagus into the pan and put the pan in the oven, sprinkle the remaining 1/4 toasted pine nuts on top.
Step 9: Roast for 20 minutes or until the chicken reaches 165 and is no longer pink.
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