Bring a large pot of water to a boil over medium-high heat. Remove the stems from the tomatoes and rinse under cold water. Use a sharp knife to score a shallow X on the bottom of each of the tomatoes. Lower the tomatoes into the boiling water and boil for 1 minute.
Use a slotted spoon to transfer the tomatoes to an ice bath and let them sit in the ice water for about 1 minute.
The tomato skin should now easily peel off. Peel the tomatoes, discarding the skin, and slice the tomatoes in half horizontally. Use a small spoon to scoop out the seeds, discard the seeds.
Roughly chop the tomatoes and place them in a large bowl. Use a potato masher to crush the tomatoes until well crushed. Set aside.
Using a long sharp knife, butterfly the pork tenderloin by slicing down the center lengthwise without cutting through the other side then open like a book and flatten evenly (about 1/4-inch thick) using a meat mallet. Lay the pork out flat with the shorter side facing you.
In a bowl mix together the breadcrumbs, Parmesan, parsley, red pepper flakes, 1/4 tsp salt and 2 TBSP of the oil. Spread the mix on the top of the pork then press the mixture flat into the pork using your hands. Roll the pork up tightly (short side facing you) and tie the ends with kitchen twine. Generously season the pork roll all over with salt & pepper.
Heat the remaining 2 TBSP of oil in a dutch oven over medium-high heat. When the oil is hot sear the pork until browned all over, 2 to 3 minutes per side. Transfer the seared pork to a plate and set aside.
Keep the dutch oven over medium-high heat and add the onion. Cook, stirring occasionally, until onion is browned and softened, about 8 minutes. Add the garlic and stir until fragrant, about 5 seconds. Add the crushed tomatoes, oregano, 1/4 tsp salt, and 1/8 tsp pepper. Cook while breaking up the tomatoes for about 5 minutes. Taste the sauce and season with salt & pepper if necessary.
Nestle the pork in the tomato sauce and reduce heat to medium-low. Place a lid on the dutch oven and simmer until pork is cooked through (an internal temperature of about 145°F), about 25 minutes.
Take the pan off the heat. Transfer the pork to a cutting board and let rest for 10 minutes.
Remove the twine from the pork then slice and serve with the sauce.
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