Heat the oil in a braising pan, ronddeau, or sauté pan. Add the bacon and cook over medium heat until fully cooked and a little crispy on the outside.
Remove bacon from the pan and set aside. Reduce heat to low and add the whole garlic cloves and the Calabrian chilis to the bacon grease. Cook until the garlic is golden and soft.
While the garlic is cooking, core and cut the cabbage into bite-size pieces. Once the garlic is fully roasted, remove the garlic and chilis from the bacon fat and set aside (if you’re using red pepper flakes, leave them in with the cabbage).
Carefully add the chopped cabbage to the pan and stir to coat. Turn the heat back up to medium and cook until cabbage is soft, about 10-12 minutes. If it starts to caramelize, you can turn the heat down or add a splash of water to help steam the cabbage.
Once the cabbage is cooked to your preference, add the cooked bacon and heavily season with salt and pepper. Taste both the bacon and the cabbage and add additional seasoning, if desired. Serve hot.
Spread garlic cloves on bread of choice and serve with the cabbage.