Preheat the oven to 375 degrees.
To make the breadcrumbs: Tear the bread into 1-inch pieces and place in a large bowl. Add 4 tablespoons of olive oil and 1 garlic clove minced, using your hands gently squeeze the bread this will help it to absorb oil. Spread out onto baking sheets and bake in the oven for about 15 minutes stirring a couple of times. Once the croutons are chewy with a crispy edge remove from the oven and set aside.
Once the croutons are cooled place them in a large bowl.

In a pot of salted boiling water blanch the kale. Drain and cool the kale, make sure to squeeze out the excess water, and roughly chop and set aside.
In a dutch oven heat 3 tablespoons of olive oil over medium heat. Add the rosemary sprigs and chilis and cook for 1 minute. Reduce the heat to medium-low and add the sliced onions. Add the thyme, salt, and pepper and cook for 10 minutes stirring often until they are soft and beginning to brown.
Add the kale to the pan with the onions, season with salt, and stir. Allow this to cook for about 15 minutes until everything is soft and incorporated.
Remove rosemary stem and pour the kale mixture over the croutons. Mixing everything together.
In the same pan, you were using pour in the Madeira bringing to a boil and reduce by half. Add the stock bring to a boil. Carefully pour over the croutons and kale and combine.
Return the pan to the stove adding 4 tablespoons of butter, once the butter begins to foam add the chestnuts, season with salt and pepper, and cook for about 4 minutes until the chestnuts are nicely cooked and the butter is browned. Add the sage leaves, combine and pour this over the croutons and kale mixture. Place the stuffing into an oven-safe dish cover with foil, and bake covered for 40 minutes. Remove the cover from the stuffing, add the 2 tablespoons butter to the top and continue to bake uncovered for 20 minutes until golden and crispy.