Preheat oven to 400 degrees F.
Peel honey squash and cut in half lengthwise. Remove seeds and slice into ½-inch thick slices. Toss with sliced red onion, garlic cloves, olive oil, cumin, paprika, sumac, salt, and pepper. Spread vegetables in an even layer on baking sheet. Roast for 40-45 minutes, flipping over vegetables halfway through.
Meanwhile, braise beans. Combine drained beans with vegetable stock, olive oil, bay leaf, garlic, salt, and pepper in a medium pot. Bring to a boil, reduce heat to low, and continue to simmer for 20 minutes.
Make garlic vinaigrette. Combine ¼ cup oil and garlic cloves in a small pot. Bring to a simmer over medium heat and continue to cook until garlic is golden brown and softened. Remove from heat and transfer to a blender. Add lemon juice, mustard, water, sugar, salt, and pepper. While the blender is on, slowly add remaining ¼ cup oil and blend until smooth. Transfer to a bowl and let cool.
Make croutons. Toss torn bread pieces with 1 tablespoon olive oil, ½ teaspoon garlic powder, and ¼ teaspoon salt. Spread on baking sheet and toast for 7-8 minutes or until golden brown. Remove from oven and let cool completely.
Toss chopped kale and shaved brussels sprouts with a couple spoonfuls garlic vinaigrette, massaging dressing into the greens.
Arrange roasted squash on serving platter. Spoon braised beans on top with a slotted spoon, discarding braising liquid. Top with kale and brussels sprouts, croutons, and goat cheese. Drizzle extra virgin olive oil and season with freshly cracked black pepper and Maldon salt. Serve with extra garlic vinaigrette on the side if desired.