Preheat the oven to 400ºF and spread the butternut squash out on a baking sheet. Toss the butternut squash with 1.5 tablespoons of olive oil. Season with 1 teaspoon of salt and ½ teaspoon of ground black pepper. Toss and bake for 25-30 minutes or until fork tender. Remove from the oven and let cool.
While the squash is roasting, prepare the chicken. Place the chicken breasts onto a cutting board and cover with plastic wrap. Pound the chicken with a meat tenderizer until the chicken is about ½-inch thick.
Add the panko and grated parmesan to a large bowl and mix and add the eggs to another bowl.
Dredge each chicken breast through the egg mixture. Allow any excess egg wash to drop from the chicken breast. Then, dredge the chicken through the panko mixture until coated. Then repeat, until both chicken breasts have been double-dredged.
Heat 2 tablespoons of olive oil in a large skillet over medium/high heat. When the olive oil is fragrant, add the chicken breasts to the pan and cook for 2-3 minutes on each side until golden brown and the internal temperature of 165ºF. Remove from the heat and let it rest for 5 minutes.
While the chicken rests, add the kale and ½ tablespoon of olive oil to a large salad bowl and massage until the kale has softened, about 1-2 minutes.
Carefully cut the chicken into bite-sized pieces and add it to the bowl with the kale. Add the butternut squash, radicchio, and shaved parmesan cheese. Toss.
Finally, add the caesar dressing to the salad and toss until all the ingredients are coated.