Bring 4 quarts water to boil in large pot. Combine shrimp, 2 tablespoons oil, cherry peppers, cherry pepper brine, ?½ teaspoon salt, and ?¼ teaspoon pepper in bowl; set aside.

Heat remaining oil, garlic, and pepper flakes in large nonstick skillet over medium-high heat until fragrant, about 1 minute. Add tomatoes and simmer until slightly thickened, about 8 minutes. Add shrimp mixture and simmer covered, stirring occasionally, until shrimp are just cooked through, about 3 minutes.

While sauce simmers, add 1 tablespoon salt and pasta to boiling water and cook until al dente. Reserve ?½ cup cooking water. Drain pasta and return to pot. Add tomato-shrimp mixture and oregano to pot and toss to combine, adding reserved pasta water as needed. Season with salt and pepper. Serve.