Cook bacon in a medium skillet until golden brown and crispy. Remove to a paper towel lined plate and crumble. Discard all but 1 tablespoon bacon grease and heat over medium-high heat. Add pineapple and stir in ancho chile powder. Cook until golden brown and caramelized, stirring occasionally, about 5 minutes. Remove from skillet and cool.
In a medium mixing bowl and using a fork, mash together red onion, garlic, cumin, avocado, and lime juice. Season generously with Kosher salt. Stir in pineapple and bacon, garnish with chopped cilantro, and serve.