Bring a large pot of salted water to a boil. Working in batches cook the kale for 2 minutes and transfer with tongs to a collander. Let cool and then squeeze all of the water with hands. Rough chop and set aside
Empty water from pot and then add 1/4 cup of olive oil, rosemary and the 1 chile broken in 3-4 pieces over medium heat. Let sizzle for about 1 minute shaking mixture around often. Then reduce heat to medium-low and add the 1 cup sliced onion, 1/2 tsp salt and a pinch of pepper. Cook and stir often for about 2 minutes or until the onion starts to soften up and turn a golden brown. About 5 minutes.
Add remaining 2 tbsp of olive oil to kale and stir to coat. Season with remaining 1/4 tsp salt and continue to cook on medium-low stirring often until the kale darkens and becomes slightly crispy on the edges. Let cool and discard the rosemary and chile pieces.
Preheat oven to 400 degrees.
Place dried bread pieces in a large bowl and drizzle with 1/2 cup olive oil. Mix around gently with hands or large spoon until the bread is coated and the olive oil is evenly distributed.
If you haven't already toast the fennel in a small pan over medium heat shaking the pan often to ensure all the seeds become golden and colour. Let cool and then in a spice mill or a clean coffee grinder coursely grind the fennel seeds
Heat a large pan over medium heat for 2 minutes. Add remaining 1/4 cup of olive oil and butter. When butter is melted add the rosemary sprigs and chili halves and let sizzle for one minute. Add crushed fennel seeds, fresh fennel, onions, thyme and garlic. Season with salt and pepper.
Saute until vegetables are tender and slightly caramelized about 6-8 minutes. Discard the rosemary and chile.
Add kale and vegetable mixture to a large 9 X 13 backing dish. Add croutons.
In the same pan bring wine to a boil over medium high heat and cook until reduced by 3/4 about 2 - 3 minutes. Add broth and bring to a bowl. Add to Kale and crouton mixture in large pan. Add 2 large eggs and mix until eggs and liquid mixture are evenly distributed.
Cover with foil and back for 30 minutes until heated through. Remove foil and bake for another 25-30 minutes or until croutons are golden. Serve immediately.