Heat 1 tablespoon oil in a large, heavy-bottomed pot over medium-high heat.
Brown the turkey in batches, breaking it into small pieces as it cooks, about 8-10 minutes total. Transfer to a plate.
Add remaining 2 tablespoons oil to the pot.
Add onions, celery, carrots, pumpkin, and both bell peppers to the pot. Saute until softened, 6-7 minutes.
Add the chipotle peppers, adobo sauce, cumin, paprika, and garlic. Cook for 2 minutes, until fragrant.
Return the turkey to pot along with the crushed tomatoes, black beans, pinto beans, beer, molasses, cocoa powder, Cajun seasoning, salt, and pepper. Bring to a simmer, reduce heat to medium-low, and cook uncovered for 45 minutes, stirring occasionally. The chili should reduce slightly and flavors should meld. Taste and adjust seasoning as desired.
Serve the chili in bowls topped with cheddar, salsa, scallions, diced jalapeño, and cilantro.