Peel the potatoes and cut them into chunks. Place them in a large pot and cover with salted water. Bring to a boil over medium-high heat, then reduce to a simmer and cook until the potatoes are tender when pierced with a fork, about 15-20 minutes. Drain the potatoes and set aside.
While the potatoes are boiling, chop the cabbage if not already done. In a separate pot, add the chopped cabbage and 2 tablespoons of water. Cover and cook over medium heat until the cabbage is soft and wilted, about 8-10 minutes. Drain off any excess water.
In a skillet over medium heat, cook the bacon slices until they are crispy, turning occasionally, about 7-10 minutes. Remove the bacon to a paper towel-lined plate to drain, then crumble or chop into small pieces once cool enough to handle. I like to save a little bit of bacon to sprinkle on top as a garnish.
Return the drained potatoes from Step 1 to the pot. Add unsalted butter and milk to the potatoes. Mash together until the mixture is smooth and creamy. If desired, adjust the texture by adding a splash more milk.
Stir the cooked cabbage from Step 2 and most of the crumbled bacon from Step 3 into the mashed potatoes from Step 4. Mix until evenly incorporated. Season with additional kosher salt and black pepper to taste. For extra flavor, I like to add a pinch of black pepper right at the end.
Transfer the finished mixture to a serving bowl or individual plates. Serve warm as a hearty side dish or enjoy it as a satisfying main. For a nice presentation, sprinkle any reserved bacon pieces on top.