Set a large saute pan over medium high heat, coat with olive oil.

Add celery and onions to saute pan, season with salt and pepper. Cook for 3 minutes or until the vegetables soften slightly, add the apples and kale. Continue to cook vegetable mixture for another 2 to 3 minutes until vegetables are soft and translucent.

Remove vegetables from pan to a separate dish. Add sweet Italian chicken sausage to the pan, breaking apart the sausage with a spatula or wooden spoon while cooking.

When sausage is cooked half way, add ½ cup marsala wine to deglaze the pan.

Add vegetable mixture back to the pan and stir to combine. Once the apples and vegetables absorb most of the wine, add the remaining ¼ cup of marsala wine. Continue cooking on medium-low heat for 15 minutes or until almost all the liquid is reduced, about 3 tablespoons will remain. Remove from heat and let cook for 5 minutes.

Set up area to wrap the sausage/vegetable mixture. Lay out a cutting board and a long piece of plastic wrap.

Add sausage mixture to the plastic wrap in a long skinny row to prevent any liquid from running of the plastic wrap. Bring the two longest ends together over the sausage mixture tightly, removing as much air as possible and compacting the mixture into a 'log' form. Mixture will still be hot, but the heat will help plastic wrap stretch and stick to itself. Tie off the plastic wrap on each end to prevent juices from running.

Using a second piece of plastic wrap, the same size as the first, wrap the mixture again, compacting the ingredients as much as possible so it will freeze as a solid piece. Place in freezer for at least 5 to 6 hours, overnight is best

Insert a long knife in one end of the pork and carefully repeat on the other side, lining the cut up with the previous one. Wiggle a wooden spoon* back and forth inside the cut to create enough space for the frozen stuffing log.

Remove the stuffing log from the freezer and discard the plastic wrap. Slide the stuffing log through the pork roast. It may require a little elbow grease, but it should go through the entire roast with some of the stuffing hanging out of each end. Any stuffing not inside the log will eventually roast off and flavor the pan sauce. Season the roast with salt and pepper.

Pre heat the oven to 375F.

Heat a roasting pan over medium high to high heat and coat with olive oil. Braise the roast on all sides until brown, about 10 minutes total. Remove the roast from the pan and discard any fat/grease.

Add the roast back to the pan along with 1 cup of chicken stock. Place roasting pan in the oven and roast for 35 minutes or until most of the liquid has been evaporated. Add remaining chicken stock and red wine. Addition chicken stock can be added if liquid is reducing too quickly. Continue roasting for 25 more minutes or until a meat thermometer reads 130F. Be sure to measure the temperature for the inner most part of the pork and not the stuffing. Total cooking time should be about 1 hour.

Allow to rest 15 minutes before slicing.

Strain the drippings from the pan. Lightly lay a piece of regular bread over the top of the sauce to remove any excess grease. Both side of the bread can be used.