Bring Olive Oil to med heat in Saute Pan and add onion. Cook until slightly translucent and add sugar. Stir until the onion is well caramelized and add balsamic and stir until evaporated.
Strip Kale of main ribs and any substantial axial ribs. Slice into 1 inch ribbons and add to onions. Reduce heat cover and allow to wilt slightly (about 10 minutes). Add tomatoes and squash and stir to coat. Cook until squash has slightly softened, add broth and cover on med-low heat for 10 to 15 minutes stirring occasionally. Broth should be almost totally absorbed.