Preheat oven to 425°. In a large bowl toss together butternut squash, rosemary, 1 tsp salt, 1/2 tsp pepper, and 1 tbsp olive oil. Transfer to a sheet pan and bake for 30 minutes, tossing halfway through.

Meanwhile, heat 1 tbsp olive oil over medium-high heat in a Dutch oven. Season pork on all sides with salt and pepper. Add to pan and sear for 1-2 minutes per side. Whisk together broth, balsamic vinegar, and brown sugar in a small bowl. When done searing add balsamic mixture and garlic to the pot and bring to a simmer. Reduce heat to low, cover, and cook for about 10-15 minutes, turning halfway through until pork is cooked to 145°. Transfer to a cutting board to rest before slicing. Turn heat to medium and simmer balsamic mixture until slightly thickened then remove from heat.

In a large bowl toss bread with 1 tbsp of olive oil and a pinch of salt. Add bread to sheet pan with the squash after it has roasted for 30 minutes. Return to oven for 5-10 minutes until bread is lightly toasted.

Add radicchio, arugula, pepitas, and green olives to a large bowl. In a small bowel whisk together Dijon, red wine vinegar, maple syrup, and 1 tbsp olive oil. When done roasting add squash and bread to the large bowl and toss together with the dressing. Add salt and pepper to taste. Divide panzanella onto plates and serve with sliced pork drizzled with balsamic reduction.