Make the bruschetta: In a medium bowl, combine 2 cups diced tomatoes, 2 pressed garlic cloves, ¼ cup julienned fresh basil, ¼ cup olive oil, 1 teaspoon salt, and ½ teaspoon black pepper. Stir to combine and set aside to marinate while you prepare the pasta.
Season the chicken: Pat 2 chicken breasts (about 1 pound total) dry and season both sides with 1 teaspoon salt, 1 teaspoon paprika, 1 teaspoon garlic powder, 1 teaspoon onion powder, ½ teaspoon dried oregano, and ½ teaspoon black pepper.
Sear the chicken: Heat 2 tablespoons olive oil in a large Dutch oven or deep skillet over medium heat. Add the chicken and cook for 4–5 minutes without moving, until deeply golden. Flip and cook another 3–4 minutes. Transfer to a plate (the chicken does not need to be fully cooked).
Build the sauce: Reduce the heat to medium and add 1 tablespoon butter. Once melted, add 1 finely diced shallot and cook for 2–3 minutes until softened. Stir in 3 pressed garlic cloves and cook for 30 seconds until fragrant.
Deglaze the pan: Pour in ¼ cup dry white wine and scrape up all the browned bits from the bottom of the pan. Let the wine simmer for about 3 minutes, or until mostly reduced.
Cook the pasta: Add 8 ounces penne, 2 cups chicken broth, and 1 cup heavy cream. Stir well, then return the chicken to the pot. Bring to a gentle simmer, cover, and cook for 12–15 minutes, stirring once or twice, until the pasta is tender and the chicken reaches 165°F.
Finish the sauce: Remove the chicken and slice it into strips. Stir 1 cup freshly grated Parmesan cheese into the pasta until the sauce is smooth and creamy.
Assemble: Top the creamy pasta with the sliced chicken, then spoon the marinated bruschetta over everything just before serving. Finish with extra Parmesan and fresh basil if desired.
