How to Make It
In a medium skillet, melt 2 tablespoons of the butter. Add half of the onion and 1 celery rib and cook over moderate heat until softened, about 5 minutes. Stir in 1 teaspoon of the sage, 2 tablespoons of the butter and the dates and remove the skillet from the heat.
In a large bowl, combine the corn bread with the contents of the skillet. Add the egg and blend well, then season with salt and pepper.
In a medium saucepan, heat 1 teaspoon of the oil. Add the remaining onion and cook over high heat until browned, about 3 minutes. Add the carrot and the remaining celery and cook over moderate heat, stirring occasionally, until softened, about 3 minutes. Add the tomato paste and cook, stirring, until glossy, about 30 seconds. Add the port, orange zest and orange juice and boil over high heat until reduced by three-fourths, about 3 minutes. Add the chicken stock, bay leaf, thyme sprig and black peppercorns and bring to a boil, then simmer over moderate heat until reduced to 3/4 cup, about 30 minutes. Strain the sauce into a small saucepan.
Preheat the oven to 350°. Scoop up 1/2 cup of the corn bread stuffing and squeeze to form it into a fat cylinder. Slide the cylinder into a quail and press to shape the quail around the stuffing. Pull the neck skin over the stuffing and secure with a toothpick. Repeat with the remaining stuffing and quail.
In a small bowl, mix the ground fennel with 1 teaspoon of salt, 1/4 teaspoon of pepper and the remaining 1/4 teaspoon of sage. Rub the quail all over with oil and sprinkle with the spice mixture.
In a large skillet, heat 1 tablespoon of the oil. Add 4 of the quail, breast side down, and cook over high heat until browned, about 4 minutes. Turn the quail and cook for 2 minutes longer. Transfer the quail to a large rimmed baking sheet. Repeat with the remaining 1 tablespoon of oil and 4 quail.
7. Roast the quail in the oven until an instant-read thermometer inserted in the center of the stuffing registers 155°, about 12 minutes.
Meanwhile, bring the port sauce to a boil. Off the heat, whisk in the remaining 1 tablespoon of butter and season with salt and pepper. Spoon the sauce onto plates, set 2 stuffed quail in the center of each and serve.