Heat the olive oil in a medium size skillet. Add the onions and toss to coat. Cook for 2 - 3 minutes.
Add the kale and the garlic and continue to cook for another 5 minutes or so. The kale should be wilted and somewhat tender and the onions and garlic should be golden.
Add a little half and half to keep things moist and continue to cook until everything is very tender. Set aside
If you choose to precook the bacon, lay the strips in a medium skillet and cook over low heat 5 -7 minutes until the bacon begins to render some fat. Remove from the pan and drain on paper towels while you prepare the tenderloin.
Trim any fat from the tenderloin. Using a sharp knife, cut along the length of the tenderloin so that it lays flat. Be careful not to cut all the way through. Set aside.
Spoon the filling into the pork tenderloin stopping a bit short of the ends. Smooth the filling out stopping about 1/2 inch from the edges.
Pull the cut edges together so that the filling is completely enclosed and the tenderloin is more or less back to its original shape.
Wrap the bacon strips around the tenderloin covering it completely. Overlap the strips as necessary to create the coverage. Secure with tooth picks. Know how many you are putting in and make sure to take the same number out prior to serving.
Place the tenderloin on a preheated grill and cook over medium high heat, turning as needed to brown and cook evenly, 20 - 25 minutes. Tenderloin is done when it reaches an internal temperature of 145 degrees.
Allow the tenderloin to rest at least 5 minutes before slicing.
Heat oven to 375 degrees. Lightly coat a baking pan with cooking spray. Combine the sliced potatoes, onions, and garlic in the pan. Add the olive oil and toss to coat. Add 1 teaspoon of coarsely ground pepper and a pinch of salt. Roast for 30 minutes.
While the potatoes roast, prepare the pork. Lay the bacon strips crosswise on a cutting board. Brush a little of the mustard down the center of the bacon. Brush mustard on one side of the pork. Lay the pork in the center of the bacon mustard side down.
Brush the remaining mustard on all the other sides of the pork.
Wrap the bacon around the pork at a slight diagonal. Fasten with toothpicks. Sprinkle the remaining pepper on all sides of the pork/bacon bundle.
Remove the pan from the oven. Place the pork on top of the potatoes and return it to the oven and roast for about 20 -25 minutes.
Check for doneness with a meat thermometer after 20 minutes. The internal temperature should be 145 degrees. Continue to roast, checking often for the correct internal temperature.
When the meat is cooked, remove the pan from the oven. Transfer the pork to a warm platter, cover loosely with foil and allow to rest for 10 - 15 minutes.
Remove the foil and cut into thick slices. Serve with the potatoes and onions.
Place the squash and cranberries in the basket of a steamer pan. Add water to the pan, cover and steam for 7 - 10 minutes. The squash should be tender and the cranberries slightly plumped. Set aside.
In a large skillet, heat the olive oil. Season the pork slices with onion herb mixture and dredge lightly in the flour. Add the slices to the skillet and cook, turning once until browned on both sides. This should take about 5 minutes. Place pork in a low oven to stay warm.
Add the broth to the pan. Scrape up any brown bits and cook over medium heat until reduced by half. Set aside.
In a medium fry pan, melt the butter. Add the apple and onion pieces, pepper flakes, and sugar. Toss to coat everything and let it cook for 4-5 minutes. The apples and onions should begin to soften.
Add the squash and cranberries to the pan. Toss to coat and cook for a minute or two. Add the reduced chicken broth and any yummy bits stirring to combine. Let this cook for another minute.
Add the pork slices and any accumulated juices and let everything get happy together for several more minutes.