Bring a large pot of water to a boil. Meanwhile, cut two shallow cross hatches into the bottom of each tomato. Add the tomatoes to the boiling water and cook for 30 seconds. Using tongs or a metal spider, transfer the par-boiled tomatoes to an ice bath.
Once chilled, peel the skin off of the tomatoes, then cut the tomatoes in half. Scrape out the seeds and pulp, then set them aside in a bowl. Dice the remaining tomatoe flesh and place them in a separate bowl. Strain the reserved tomatoe pulp/seeds into the diced tomatoes, then discard the seeds.
Add the guanciale to a large cold skillet. Begin heating the skillet over medium-low heat and cook the guanciale until most of the fat has rendered out, about 8-10 minutes. Using a slotted spoon, remove the cooked guanciale, leaving the rendered fat in the skillet.
Add the onion and cook until translucent, 3-5 minutes. Then, add the chopped calabrian chili and cook for 30 seconds to 1 minute or until fragrant.
Deglaze the pan with the wine and cook for 1 minute or until the alcohol burns off. Make sure to scrape the fond off the bottom of the pan using a wooden spoon or spatula.
Add the 1 cup of the chopped tomato mixture and the tomato puree to the skillet. Cook the sauce, while stirring periodically, for 10-12 minutes or until thickened.
Meanwhile, bring a pot of water to a boil, then season with 1 tablespoon of salt.
Add the fresh pasta to the boiling and cook until al dente, about 2 minutes. Using tongs, transfer the cooked pasta to the large skillet with the tomato sauce. Reserve the cooking water.
Add about ½ cup of cooking water to the skillet, then stir/toss to combine the sauce with the pasta.
Turn off the heat and stir in the pecorino cheese, reserved guanciale, and a drizzle of extra virgin olive oil. Season the pasta to taste with salt and pepper.
Serve immediately and garnish with a sprig of basil leaves.