1Warm 1 tablespoon olive oil in a large saucepan over medium-high heat. Add the sausage and cook, stirring and breaking it up, until lightly browned, about 8 minutes. Transfer the sausage to a bowl, straining off any fat if necessary. Reduce the heat to medium and add a drizzle of olive oil (unless there is some fat in the pan) and add the onion. Cook, stirring, until tender, about 6 minutes. Stir in the garlic and cook until fragrant, about 1 minute. Add the tomatoes, olives, wine, balsamic, oregano, ground fennel, and red pepper flakes and stir to loosen any browned bits on the pan bottom. Bring to a boil, reduce the heat to medium-low, add the reserved sausage, and simmer about 10 minutes.
2While the sauce is simmering, bring a large pot of salted water to a boil over high heat. Add the tortellini and cook according to the package directions. Drain well.
3Add the tortellini to the sauce and stir to coat. Re-warm over medium-low heat just until heated through. Serve, garnished with Parmesan.