Start by roasting the poblano peppers over an open flame. When charred on all sides, carefully place them in a bag to sweat. After 5-10 minutes remove them from the bag, scrape off the skin and dice the peppers. Set aside.
In a large pot or Dutch oven over medium heat, cook the bacon until crisp. Remove the bacon from the pot and set it aside. Leave the bacon drippings in the pot.
In the same pot with the bacon drippings, add the diced smoked brisket. Brown the brisket on all sides, then remove it from the pot and set it aside with the cooked bacon.
Add the diced onion and minced garlic to the pot. Sauté until the onions are soft and translucent, about 5 minutes.
Stir in the smoked paprika, chipotle pepper in adobo, cumin, oregano, chili powder, cinnamon, bay leaves and chocolate. Cook for an additional 1-2 minutes, until the spices are fragrant.
Deglaze the Pot. Pour in the Worcestershire sauce and coffee, scraping the bottom of the pot to loosen any browned bits.
Preheat your smoker to 350F.
Add Remaining Ingredients: Return the cooked bacon and brisket to the pot. Add the diced roasted poblano and jalapeno peppers, beef broth, crushed fire-roasted tomatoes, and chili beans. Stir well to combine. Tip: you can also add the beans towards the end of the cook to keep them plump.
Bring the chili to a simmer on your stove top.Then transfer it to the smoker and let it simmer gently for at least 1 hour, stirring occasionally. For even better flavor, let it simmer for 2-3 hours.
Adjust seasoning, taste for salt, pepper and adjust accordingly. Remove the bay leaves.
Serve hot garnished with shredded cheese, sour cream, avocado, cilantro, corn chips, tortillas.
Notes
Make it the day before - I know, I know planning is hard for some of us :) letting the Chili sit for a while will allow the flavors to meld and fully develop. Low and Slow - don't rush the process; this helps all the flavors to develop and the meat to become tender. Texture - you want thick, hearty with chunks of meat and beans. Add the beans towards the end of the cookBuild layers of flavor - start by browning your meat, sauté the aromatics, before adding liquids. Be mindful of the spices you use and how much you add. Taste as you go and adjust the seasoning accordingly. Don't Forget Acidity: balance the flavor with a splash of vinegar or citrus to brighten up the flavors and add depth.Add the beans towards the end of the cook to avoid them from becoming mushy and soft. Texture!