Heat 1 tablespoon olive oil in a Dutch oven or large high-walled skillet over medium-high heat. Add ground turkey and saute over medium-high heat until meat is no longer pink. Remove meat from pan with a slotted spoon.
Heat remaining 1 tablespoon olive oil in same pan over medium-high heat. Add butternut squash, onion, carrot, and celery to pan and cook over medium-high heat 3-5 minutes until onion is translucent. Add garlic and cook 1 additional minute until fragrant.
Pour half and half into pot and let simmer 3-5 minutes until liquid is nearly evaporated. Add wine to pot and let simmer an additional 5-8 minutes until wine is nearly evaporated.
Add browned turkey, tomatoes, sugar, tomato paste, Italian seasoning, and bay leaf. Bring sauce to a simmer over medium-high heat, breaking up tomatoes against the side of pan with a wooden spoon.
Reduce heat to low and allow sauce to simmer uncovered at least 45 minutes or up to 1-1/2 hours, stirring occasionally. If at any point sauce gets too dry, add a splash of water as needed.
Remove bay leaf from sauce. Season sauce with salt and pepper to taste and fold warm cooked pasta into sauce when ready to serve. Top with Parmesan and basil for serving. Enjoy!