1. Preheat oven to 450 degrees F. Chop 1 bunch broccoli into florets and spread on a large baking pan. Toss with 1 Tbs. olive oil, 1/4 tsp. each kosher salt and pepper and roast until browned, about 15 to 20 minutes.
2. In a nonstick skillet over medium heat, cook 3 to 4 Italian sausages (12 oz. total), turning occasionally, until lightly browned, about 3 to 4 minutes. Reduce heat to medium-low, cover, and cook until the sausages are cooked through, about 15 minutes longer. Transfer the sausages to a cutting board, do not drain skillet.
3. Add 2 pints grape tomatoes, 2 peeled and smashed garlic cloves, and 1 tsp. sugar to the skillet. Cook over medium-high heat, stirring often, until tomatoes have softened and started to brown and burst, about 5 to 6 minutes. Remove from heat and add 3 Tbs. water. Using a potato masher, mash tomatoes into a sauce. Cut sausages into slices and…