Heat 2 tablespoons of olive oil in a large, heavy bottomed pot or Dutch oven over medium high heat until shimmery. Working in batches so you do not crowd the pan, add the beef pieces in the pot, season with salt and pepper and sear them until they form a deep brown crust on all sides, about 5 to 8 minutes per batch. Transfer the browned beef to a plate and set it aside.

Lower the heat to medium and add the remaining 1 tablespoon of olive oil to the same pot. Toss in the finely diced yellow onion and diced jalapeños, cooking for 5 to 6 minutes until the onions turn translucent and soft, scraping up the browned beef bits from the bottom of the pot.

Stir in the minced garlic, chili powder, ground cumin, smoked paprika, dried oregano, and ground cinnamon. Stir constantly for about 1 minute until the spices become highly aromatic and darken slightly.

Add the tomato paste and the chopped chipotle peppers with their adobo sauce to the pot. Stir well to coat the vegetables, cooking for another 2 minutes until the paste turns a deep brick-red color.

Return the browned beef and any accumulated juices back into the pot. Pour in the crushed tomatoes and beef stock, then drop in the bay leaves. Stir until everything is completely combined.

Bring the chili to a boil, then immediately lower the heat to low so it reaches a gentle simmer. Cover the pot with a lid and let it cook for 2 hours, stirring occasionally to make sure nothing sticks to the bottom.

Remove the lid and continue to simmer uncovered for an additional 20 to 30 minutes, or until the beef is melt-in-your-mouth tender and the chili has thickened to your liking.

Taste the chili and adjust the salt and pepper if needed. Serve with your favorite chili toppings and enjoy!