Preheat oven to 375°F.
Bring a few inches of water to a boil in a deep skillet. Salt water, add broccoli rabe or broccolini, cook 3-4 minutes then drain well and chop into 1 1/2-inch pieces.
Combine meats in large bowl with salt, pepper, breadcrumbs, milk, egg, Parm, garlic and rosemary then form meatloaf on a parchment-lined baking sheet into a rectangle about 12x15 inches and 3/4-inch thick. Scatter the shredded cheese across the meat and top with the broccoli rabe or broccolini then the cherry peppers, stopping a few inches short of the end of the rectangle. Roll the loaf and press seam together to close, smooth out the roll of meatloaf and drizzle with EVOO. Roast 1 hour or until it reaches an internal temperature of 150-155°F. Let rest a few minutes before serving.
While the meatloaf cooks, prepare the sauce: Heat EVOO in saucepot, add finely chopped vegetables and stir until golden and soft. Add garlic, season with salt and pepper then add rosemary and stir to soften 3-4 minutes. Add tomato paste and stir a minute more, add wine and cook a minute or two. Add consommé and tomatoes, and simmer 20 minutes to thicken.
Slice meatloaf and set into a generous puddle of red wine sauce. Make a well in a scoop of garlicky mashed potatoes to serve alongside.
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