Add the olive oil, smashed garlic and red chile flakes to a large saute pan. Turn the heat to medium-high and allow the garlic to become fragrant and the oil heated. Once heated, add the tomatoes and oregano, and season with salt. Stir to combine. Cook until the tomatoes release their water, 2 to 3 minutes. Deglaze the pan with the white wine. Cook until the wine is bubbling and has begun to reduce, about 1 minute. Add the squid, stir to combine, and cook until the squid becomes opaque in color--be careful not to overcook it! Taste and adjust the seasoning as needed.
Meanwhile, bring a large pot of salted water to a boil. Add the tagliatelle and cook for about 2 minutes. Remove the pasta from the water and add it directly to the sauce along with about 2 tablespoons of the pasta water, some more oregano, some grated parm and a drizzle of big fat finishing oil. Gently toss to combine.
Plate and garnish with more grated parm.