Pork Tenderloin & Sauce:
Heat a tablespoon of the olive oil in a 12-inch skillet over medium heat. Add the onions and cook, stirring occasionally, until softened and light golden brown, about 5 – 8 minutes. If needed, add a bit of water to the pan to prevent scorching.
When the onions are caramelized, add the orange juice, zest, balsamic & dried cherries, cover and cook over low heat until cherries are plump and onions very soft, about 5 minutes longer. Add spinach and cook, uncovered until spinach is wilted and all the liquid has evaporated, about 5 minutes more. Season to taste with salt and pepper. Leave to cool as you prep the tenderloin.
Pork Tenderloin & Sauce:
Heat the oven to 425°F.
Slice the tenderloin, lengthwise into one flat piece: Cut about an inch into the tenderloin, then using small slices and turning the tenderloin bit by bit, keeping the outside portion as even as you can, cut the tenderloin at about 3/4 inch to one inch, until it lays flat. (Basically, cut it at a spiral.) Place between two pieces of plastic wrap cut side up and pound gently until; it reaches a thickness of about 1/2″.
In a small bowl, mix the ground allspice and 1/4 teaspoon black pepper then stir in about 1/2 tablespoon olive oil. Rub the mixture on both sides of the pork and season generously with salt. Spread the stuffing mixture down the center of the cut side of the tenderloin, leaving a generous inch and a half along one of the long edges bare. Sprinkle with bacon & cheese and roll tightly, from the long end without the unspread edge towards the bare edge. Tie with butcher twine at 1-inch intervals.
Heat the remaining 2 tablespoons olive oil in an ovenproof 12-inch skillet over medium-high heat. Brown the pork on all sides until golden, about 5 to 6 minutes. Transfer to the oven and roast until an instant-read thermometer inserted in the thickest part of a tenderloin reads 145 to 160 degrees F, 10 to 15 minutes. Transfer the pork to a cutting board and tent with foil.
Set the skillet over medium-high heat, add the wine, and deglaze the pan by scraping up the cooked bits with a wooden spoon. Bring to a boil & reduce the wine by about half, 1 to 2 minutes. Add the chicken broth, bring to a boil, and reduce by about half, 2 to 3 minutes. Turn off heat, remove from burner & add butter, gently swirling it around with a fork until melted. Season to taste with salt and pepper.
Remove the strings from the pork and slice it into 3/4-inch-thick slices. Serve drizzled with the sauce.
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