Dice the onion and bell pepper into 1/2-inch pieces, mince the garlic, and chop the fresh cilantro. Measure out all your spices (chili powder, allspice, thyme, cinnamon, and nutmeg) into a small bowl so they're ready to go when you need them. Having everything prepped and organized makes the cooking process smooth and prevents burning spices by giving you time to add them at just the right moment.
Heat the olive oil in a large pot over medium-high heat, then add the diced onion, bell pepper, and minced garlic. Season with kosher salt and freshly ground black pepper, and cook for 5-8 minutes, stirring occasionally, until the vegetables are soft and the onion becomes translucent. Once the vegetables have softened, add the spice mixture from Step 1 and cook for about 1 minute, stirring constantly, until the spices become fragrant and the raw spice smell goes away. I like to bloom my spices in the hot oil like this—it awakens all those jerk flavors and creates a much deeper, more complex base for the whole chili.
Add the shredded cooked turkey to the pot and stir to coat it with the spice-infused oil, then pour in the chicken broth and stir well. Add the stewed diced tomatoes (with their juices), drained cannellini beans, drained black beans, and pickled jalapeños. Stir everything together until well combined, then bring the mixture to a simmer over medium heat. Once simmering, reduce the heat to low and let the chili cook gently for 30 minutes. This slower simmer allows all the flavors to meld together and deepens the jerk seasoning throughout the broth.
After the 30-minute simmer, remove the pot from heat. Melt the bittersweet chocolate (you can do this quickly by stirring it in directly—the heat of the chili will melt it), then stir in the cornmeal and chopped cilantro from Step 1. The chocolate adds a subtle richness that deepens the jerk spice complexity without making the chili taste sweet, and the cornmeal gives it a pleasant, slightly thickened texture. Let the chili sit undisturbed for 10 minutes to allow the flavors to settle and the cornmeal to fully hydrate.
Stir the chili gently to recombine everything, then taste and adjust the seasoning with additional kosher salt and freshly ground black pepper as needed. The chili should have bold jerk spice, a slight heat from the jalapeños, and balanced complexity from the chocolate. Serve hot and enjoy the authentic Caribbean-inspired flavors.